1977_The sulfophosphovanillin reaction for serum lipids a reappraisal_K. R. Johnson

黄磷生产工艺编辑：科技博士В.А..叶尔绍夫。

科技副博士B.H.别洛夫列宁格勒，（化学出版社）列宁格勒分社，1979年。

黄磷工艺学，B.H.别洛夫，А. П.博尔莎科娃，Я. Б. 丹尼斯等。

职业编辑：В.А.叶尔绍夫和科技副博士B.H.别洛夫。

1979年，336 页。

本书分析研究了黄磷的物理化学性质，在固相和液相还原磷酸钙的热力学和动力学现代知识，磷矿、硅石共熔体物理化学性质的系统化资料。

详细叙述了黄磷生产的全部过程和主要设备，原料产地与资源，生产废料的利用途径与具体方法。

特别值得注意的是工艺分析，黄磷电炉中的物流状态，炉子结构，电气和工艺指标。

本书可供黄磷生产和加工企业工程技术人员，科研设计院专家使用。

也适用于化工工艺高等院校的教师、研究生和大学生。

336页，99张表，79个插图，316篇参考文献。

编辑：В. А. 斯坦科维奇，技术编辑：3. Е.马尔科夫，校对：Г. А. 列别杰夫，装订：Н. А. 涅菲多夫。

出版：1979年2月16日，Поди, кпеч.：1979年8月3日，纸张规格：60X901/16，Бум.1号字体，高级印刷品. Усл. печ. л. 21,0. Уч.-изд. л. 23,7. 印数3000本。

Зак. № 67。

价格1卢布50k,产品号1650。

化学出版社列宁格勒分社，191186, 列宁格勒, Д-186, Невскийпр., 28。

苏联国家出版委，尤金雄鹰名誉« Союзполиграфпрома»， 获得劳动红旗勋章的列宁格勒第二印刷厂，198052, 列宁格勒, Л-52, Измайловскийпр., 29。

版权：化学出版社，1979年。

序言我国黄磷工业在短时间内从小车间发展到现代化的大型工厂。

由于党和政府的关怀爱护，形成了拥有现代技术的工业企业，在黄磷厂建立了大功率的独特装置，能加工处理各种磷矿原料。

目前，科学家、设计师、建筑师及工厂的工程技术人员正在研究改进现有的磷矿处理备料方法，研究黄磷生产新方法和残渣处理利用，自动化的工艺控制系统，建立无废渣的黄磷生产工艺。

你从未见过的美丽化学视频长度在30秒到6'30不等，请在wifi环境下观看《美丽化学》：美丽的化学反应这很可能是有史以来，中国人制作的最酷的关于化学的科学传播作品，纯粹化学，纯粹美丽。

这就是由中国科学技术大学先进技术研究院和清华大学出版社联合制作的一个原创数字科普项目《美丽化学》。

这个9月30日上线英文版的网站，一上线即刻在网络上引起了轰动，短短两周，包括美国《时代周刊》官网等媒体都对他进行了报道和高度评价。

2013年诺贝尔奖和平奖得主“禁止化学武器组织”特别提出希望能在他们的最新纪录片中使用这些视频。

近日，《美丽化学》又成功入围由美国国家科学基金会和美国《大众科学》杂志举办的VIZZIES国际科学可视化竞赛大奖，同时入围“游戏/应用”（Game/App）和“视频”（Video）两个奖项的竞选，截至目前，还没有来自中国大陆的团队在竞赛中取得过名次。

《美丽化学》包括“化学反应”和“化学结构”两部分，分别从宏观和微观两个尺度展现独特的化学之美。

在“化学反应”使用最新的4k高清摄影机捕捉化学反应中的缤纷色彩和微妙细节。

在“化学结构”部分，使用先进的三维电脑动画和互动技术，展示近年来在《自然》和《科学》等国际知名期刊中报道的美丽化学结构。

来自中国科学技术大学科技传播与科技政策系特任副研究员梁琰负责了这个项目。

加入中科大之前，他作为自由职业者为来自世界各地的研究人员提供科学可视化服务，他的作品作为封面发表在《科学》、《自然-材料》、《自然-生物技术》、《自然-光子学》等知名学术刊物。

2012年，他作为科学动画师，参与开发《地球上的生命》，这是一本具有革命意义的基于苹果iBooks平台的数字教科书。

2014年3月，梁琰加入中国科技大学科技传播系，《美丽化学》项目也随之正式启动，首先上线的英文版大概经历了7个月左右。

2014年10月底，中文版网站也顺利上线。

这些精致、美丽的视频，作为中国科学传播最高的制作水平必将更大范围的被人知晓和传播。

Bro¨nsted acid ionic liquid-catalyzed direct benzylation,allylation and propargylation of 1,3-dicarbonyl compounds with alcohols as well as one-pot synthesis of 4H -chromenesKazumasa Funabiki *,Takuya Komeda,Yasuhiro Kubota,Masaki MatsuiDepartment of Materials Science and Technology,Faculty of Engineering,Gifu University,1-1Yanagido,Gifu 501-1193,Japana r t i c l e i n f oArticle history:Received 14April 2009Received in revised form 3July 2009Accepted 3July 2009Available online 8July 2009Keywords:Ionic Bro¨nsted acid catalyst Substitution1,3-Dicarbonyl compounds Alcohola b s t r a c tRecyclable ionic Bro¨nsted acid was prepared in nearly quantitative yield by reacting 1-butylimidazole with an equimolar amount of 1,3-propanesultone,followed by treatment with an equimolar amount of tri-fluoromethanesulfonic acid.The ionic Bro¨nsted acid-catalyzed direct benzylation,allylation and prop-argylation of 1,3-dicarbonyl compounds with various alcohols in ionic liquid [N -ethyl-N -methyl imidazolium trifluoromethanesulfonate (EMIOTf)],at 100 C for 3h proceeded smoothly to give the cor-responding products in good to excellent yields without the use of any hazardous or volatile solvents and without any by-product such as salts.Furthermore,tandem benzylation–cyclization–dehydration of 1,3-dicarbonyl compounds to give functionalized 4H -chromenes was also achieved in this catalytic reaction.Ó2009Elsevier Ltd.All rights reserved.1.IntroductionThe alkylation of 1,3-dicarbonyl compounds usually requires not only the transformation of 1,3-dicarbonyl compounds into more re-active species,such as enolates by reacting the 1,3-dicarbonyl com-pounds with base,but also the use of alkyl halides,since the hydroxyl group is not a good leaving group and 1,3-dicarbonyl compounds do not have high nucleophilicity.However,these requirements are limitations,as is the production of a salt as a by-product.From the standpoint of atom-economical and environmentally friendly chemistry,the catalytic direct carbon–carbon bond formation of 1,3-dicarbonyl compounds using alcohols in place of alkyl halides is one of the most ideal and salt-free reactions in organic synthesis,since steps are not needed for the generation of reactive enolate or for pre-conversion to the alkyl halides,and only water is generated as a by-product.Although some excellent catalysts,such as indium trichloride,1proton-exchanged montmorillonite,2trifluoromethanesulfonic acid,3p -toluenesulfonic acid,3,4polymer-supported p -toluenesulfonic acid,4metal triflate,5iron(III)chloride 6and hetropolyacid 7have recently been examined for catalytic direct carbon–carbon bond formation in active methylene compounds using alcohols as alkylating reagents,most of the reported reactions require hazardous or volatile solvents,such as nitromethane,dichloromethane,acetonitrile and toluene,and the re-covery and reuse of the catalysts far are still limited.2,4,5b Therefore,thedevelopment of a much more convenient,reusable,environmentally friendly system for the catalytic alkylation of 1,3-dicarbonyl com-pounds without the use of any hazardous or volatile solvents is needed.In this report,for the first time,we present our recyclable Bro¨nsted acid-catalyzed direct benzylation,allylation and propargylation of 1,3-dicarbonyl compounds with various alcohols as well as the tan-dem benzylation–cyclization–dehydration of 1,3-dicarbonyl com-pounds to give functionalized 4H -chromene in an ionic liquid system.2.Results and discussion2.1.Preparation of Bro¨nsted acid ionic liquid catalyst 1Recyclable Bro¨nsted acid ionic liquid catalyst 1,which was used for esterification,was prepared by modification of the method reported by Forbes et al.8as shown in Scheme 1.1-ButylimidazoleNNn -Bu SO 2O TfO 150°C,5hNN 3H n -Bu rt,20min 1(97%)CF 3SO 3H (1equiv.)NN SO 3n-Bu(98%)Scheme 1.Preparation of Bro¨nsted acid ionic liquid catalyst 1.*Corresponding author.Tel.:þ812932599;fax:þ812932794.E-mail address:funabiki@gifu-u.ac.jp (K.Funabiki).0040-4020/$–see front matter Ó2009Elsevier Ltd.All rights reserved.doi:10.1016/j.tet.2009.07.012Tetrahedron 65(2009)7457–7463Contents lists available at ScienceDirectTetrahedronjournal homepage:www.elsevie /locate/tetwas allowed to react with an equimolar amount of 1,3-propane-sultone at room temperature to produce zwitterionic imidazolium salt in quantitative yield.Treatment of this zwitterionic imidazo-lium salt with an equimolar amount of trifluoromethanesulfonicacid at 150 C gave the Bro¨nsted acid ionic liquid catalyst 1in quantitative yield.2.2.Bro¨nsted acid ionic liquid 1-catalyzed direct benzylation,allylation and propargylation of 1,3-dicarbonyl compounds 2with alcohols 3The reaction of 2,4-pentanedione (2a )with 1-phenylethanol (3a )was conducted in the presence of 5mol %of the prepared Bro¨nsted acid ionic liquid catalyst 1in a commercially available ionic liquid,N -ethyl-N -methyl imidazolium trifluoromethanesulfonate (EMIOTf),at 100 C for 3h.After the mixture was allowed to cool to room temperature,repeated extraction with a mixed solvent of diethyl ether and hexane (v/v ¼1:1)from EMIOTf,evaporation under vacuum,and chromatography with silica gel gave 3-(1-phenyl-ethyl)pentane-2,4-dione (4aa )in 77%yield,together with a small amount (7%)of (E )-but-1-ene-1,3-diyldibenzene (5)(styrene dim-mer)(Table 1,entry 1).Other ionic liquids carrying other counter anions,such as N -butyl-N -methylimidazolium tetrafluoroborate (BMIBF 4)and N -butyl-N -methylimidazolium hexafluorophosphite (BMIPF 6),were used (entries 2and 3).As a result,in the case of BMIBF 4,only trace amount of the product 4aa was formed,and 1,10-oxybis-(ethane-1,1-diyl)dibenzene (bis(1-phenylethyl)ether)was obtained as a main product (33%yield,dr ¼50:50)(entry 2).The reaction in BMIPF 6proceeded smoothly to give 4aa in 94%yield (entry 3).Surprisingly,when the ionic liquid catalyst 1was not added,the reaction of diketone 2a with alcohol 3a also proceeded to give the corresponding product 4aa in lower yield (61%),to-gether with styrene dimmer 5(20%yield)(entry 4).9The use of an equimolar amount of diketone 2a resulted in significant decrease of the yield (39%)of 4aa (entry 5).Employing trifluoromethansulfonicacid in place of the Bro¨nsted acid ionic liquid catalyst 1gave the similar yield (74%)of 4aa ,together with styrene dimmer 5(8%)as well as 4-phenylpentan-2-one (20%)(entry 6).The results of the Bro¨nsted acid ionic liquid 1-catalyzed reaction of 1,3-diketones 2,such as 2,4-pentanedione (2a )and 1,3-diphenyl-propane-1,3-dione (2b ),with various alcohols,such as 1-phenyl-ethanol (3a ),diphenylmethanol (3b ),(E )-1,3-diphenylprop-2-en-1-ol (3c ),(E )-pent-3-en-2-ol (3d ),and 1,3-diphenylprop-2-yn-1-ol (3e )in EMIOTf,are summarized in Table 1.In the case of diphenylmethanol (3b ),the reaction also proceeded smoothly to give 3-benzhy-drylpentane-2,4-dione (4ab )in 94%yield (entry 7).Allylation and propargylation using (E )-1,3-diphenylprop-2-en-1-ol (3c ),(E )-pent-3-en-2-ol (3d )and 1,3-diphenylprop-2-yn-1-ol (3e )also proceeded to give the corresponding allylated and propargylated diketones 4ac ,4ad and 4ae in 47–90%yields (entries 8–10).1,3-Diphenylpropane-1,3-dione (2b )participated well in the reaction with 1-phenylethanol (3a )and diphenylmethanol (3b )to produce the corresponding ben-zylated diketones 4ba and 4bb in 81–98%yields,without formation of the styrene dimer 5(entries 11and 12).The results of the Bro¨nsted acid ionic liquid-catalyzed reactions of ethyl 3-oxobutanoate (2c ),ethyl 3-oxopentanoate (2d )and ethyl 3-oxo-3-phenylpropanoate (2e )with various alcohols are sum-marized in Table 2.The use of various alcohols 3a –c ,e gave the corresponding benzylated,allylated and propargylated products 4cb ,4cc and 4ce in 76–91%yields (entries 2–4).However,the re-action of 2c with 1-phenylethanol (3a )gave the corresponding ketoester 4ca in 30%yield,together with a moderate amount (40%)of styrene dimer 5,probably due to lower nucleophilicity of ketoester 2c than those of diketones 2a ,b .Other ketoesters 2d ,e also participated well in the catalytic reaction with alcohol 3b to give the corresponding products 4db and 4eb in 89–97%yields (entries 5and 6).Diastereoselectivities of the products 4ca ,4cc and 4ce are quite low.To confirm the reaction mechanism for the formation of styrenedimer 5,the Bro¨nsted acid ionic liquid-catalyzed reaction of 1-phenylethanol (3a )in EMIOTf in the absence of 1,3-dicarbonyl compound 2was carried out,as shown in Scheme 2.Table 1Bro¨nsted acid ionic liquid 1-catalyzed direct benzylation,allylation and prop-argylation of 1,3-diketones 2a ,b with various alcohols 3EMIOTf,100°C,3h1(5mol%)R 34OH R 1R 2O O +32R 1R 2O O R 4R 343a R 3=Ph,R 4=Me 3b R 3=R 4=Ph3c R 3=(E )-PhCH=CH,R 4=Ph 3d R 3=(E )-MeCH=CH,R 4=Me 3e R 3=PhC C,R 4=Ph 2a R 1=R 2=Me 2b R 1=R 2=PhNNEt TfO EMIOTfNNn -Bu BMIBF 4BF 4NNn -Bu BMIPF 6PF 6Yields of isolated products.Values in parentheses show the yields of styrene dimer 5.bBMIBF 4was used in place of EMIOTf.1,10-Oxybis (ethane-1,1-diyl)dibenzene was obtained in 33%yield.cBMIPF 6was used in place of EMIOTf.dIL catalyst 1was not added.eAn eqimolar amount of 2a was used.fTrifluoromethanesulfonic acid was used in place of IL catalyst 1.4-Phenylpentan-2-one was also obtained in 20%yield.PhPh5K.Funabiki et al./Tetrahedron 65(2009)7457–74637458As a result,styrene dimer 5was formed as a sole product in 50%yield.This result can be explained by the following mechanism:(1)protonation of the hydroxyl group of alcohol 3a and successive dehydration produces the benzyl cation,and subsequent deproto-nation gives styrene.(2)The obtained styrene attacks the other benzyl cation,and deprotonation at the b -carbon gives styrene dimer 5.After having successfully developed an efficient benzylation of 1,3-diketones 2a ,b and ketoesters 2c ,d ,e ,we then sought to apply this methodology to the synthesis of highly functionalized 4H -chromene 10via catalytic tandem benzylation,cyclization and de-hydration of the 2-(hydroxy(phenyl)methyl)phenol (3f ),prepared from salicylaldehyde and phenyllithium,as described in Table 3.This catalytic tandem reaction of 3f with diketones 2a ,b and ketoesters 2c ,d ,e proceeded smoothly to produce the corresponding 4H -chromenes,such as 1-(2-methyl-4-phenyl-4H -chromen-3-yl)-ethanone (6af ),(2,4-diphenyl-4H -chromen-3-yl)(phenyl)methanone (6bf ),ethyl 2-methyl-4-phenyl-4H -chromene-3-carboxylate (6cf ),ethyl 2-ethyl-4-phenyl-4H -chromene-3-carboxylate (6df )and ethyl 2,4-diphenyl-4H -chromene-3-carboxylate (6ef ),in good to excellent yields (77–98%),respectively.Furthermore,the Bro¨nsted acid ionic liquid-catalyzed reactions of 1,3-diphenylpropane-1,3-dione (2b )with an equimolar amount of a highly activated tertiary alkynol,1,1,3-triphenylprop-2-yn-1-ol (7),also proceeded smoothly to give not a propargylated product,but rather a dienyl product,1,3-diphenyl-2-(1,3,3-triphenylallyli-dene)propane-1,3-dione (8),in 66%yield,as shown in Scheme 3.Table 3Bro¨nsted acid ionic liquid 1-catalyzed tandem direct benzylation,cyclization and dehydration of 2with the alcohol 3f1(5mol%)R1R 2O O+3f2a R 1=R 2=Me 2b R 1=R 2=Ph2c R 1=Me,R 2=OEt 2d R 1=Et,R 2=OEt 2e R 1=Ph,R 2=OEtEMIOTf,100°C,3hO R 2O 6R 1R 1R 2O O OHOHOH2Yields of isolated products.Table 2Bro¨nsted acid ionic liquid 1-catalyzed direct benzylation,allylation and prop-argylation of ester 2with various alcohols 31(5mol%)R3R 4OH R1O O +32c R 1=Me 2d R 1=Et 2e R 1=PhOEtO O R 4R 343a R 3=Ph,R 4=Me 3b R 3=R 4=Ph3c R 3=(E )-PhCH=CH,R 4=Ph 3e R 3=PhC C,R 4=PhEMIOTf,100°C,3h2R 1Yields of isolated products.Values in parentheses show the yields of styrene dimer 5.bDetermined by GC.PhPhMe 5(50%)PhMeOH EMIOTf,120°C,3h1(5mol%)3a Scheme 2.Proposed reaction mechanism for the formation of 5.EMIOTf,100°C,24h1(5mol%)PhOH PhPhO O +72bPh PhO O Ph 8(66%)PhPh PhPhScheme 3.Bro¨nsted acid ionic liquid 1-catalyzed reaction of 1,3-diphenylpropane-1,3-dione (2b )with tertiary alkynol 7.K.Funabiki et al./Tetrahedron 65(2009)7457–74637459According to the previous report by Sanz et al.,3b this product could be produced by the tandem Meyer–Schuster rearrangement of tertiary alkynol 7,aldol condensation with diketone 2b and de-hydration,as shown in Scheme 4.2.3.Reuse of the Bro¨nsted acid ionic liquid catalyst 1Finally,reuse of the Bro¨nsted acid ionic liquid catalyst 1was carried out,as shown in Scheme 5.After the initial use of the catalyst 1in EMIOTf,the product 4aaand styrene dimer 5were extracted from EMIOTf three times with a mixed solvent of diethyl ether and hexane (1:1).Concentration of the mixed organic layer and purification by column chromatogra-phy gave the product 4aa with a trace amount of 5.Reuse of the catalyst in the second and third cycles gave the product 4aa in al-most the same yield along with a trace amount of 5.3.ConclusionIn conclusion,we have developed a new recyclable Bro¨nsted acid-catalyzed direct benzylation,allylation and propargylation of 1,3-dicarbonyl compounds with various alcohols in an ionic liquid,N -ethyl-N -methyl imidazolium trifluoromethanesulfonate (EMIOTf),without the use of any hazardous or volatile solvents and without any by-product such as salts.Furthermore,this method could also be applied to the tandem benzylation–cyclization–dehydration of 1,3-dicarbonyl compounds to give functionalized 4H -chromenes in good to excellent yields.4.Experimental4.1.General1H (400MHz)or 13C (100MHz)NMR spectra were measured with a JEOL a -400FT-NMR spectrometer in deuteriochloroform (CDCl 3)solution with tetramethylsilane (Me 4Si)as an internal stan-dard.Melting points were obtained on a Yanagimoto MP-S2micro melting point apparatus and are uncorrected.IR spectra were mea-sured on a SHIMADZU FT-IR 8100A spectrometer.HRMS were measured on a JEOL JMS-700mass spectrometer.LRMS were mea-sured on a JEOL JMS-K9mass spectrometer.The pure products were isolated by column chromatography using silica gel (Wakogel C-200,100–200mesh,Wako Pure Chemical Ind.,Ltd.).N -Ethyl-N -methyl imidazolium trifluoromethanesulfonate (EMIOTf)was a gift from the Central Glass Co.,Ltd.All chemicals were of reagent grade and,if necessary,purified in the usual manner prior to use.4.2.Preparation of 1-butyl-3-(3-sulfopropyl)-1H -imidazol-3-ium trifluoromethanesulfonate (1)To propanesultone (3.908g,31.97mmol)in a two-necked flask under argonwas slowly added 1-butylimidazole (4.005g,32.25mmol),and the mixture was stirred for 30min at room temperature.Repeated washing of the obtained solid with toluene (20ml Â5)and Et 2O (20ml Â5),and evaporation under vacuum at room temperature gave 3-(1-butyl-1H -imidazol-3-ium-3-yl)propane-1-sulfonate in 98%yield (7.797g).4.2.1.3-(1-Butyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonateYield 98%;Mp 176.7–177.1 C;IR (KBr)1566(C ]C),1179(SO),1038(SO)cm À1;1H NMR (D 2O,400MHz)d 0.99(t,J ¼7.37Hz,3H,C H 3CH 2CH 2CH 2),1.38(sext,J ¼7.37Hz,2H,CH 3C H 2CH 2CH 2),1.88(quint,J ¼7.37Hz,2H,CH 3CH 2C H 2CH 2),2.32(quint,J ¼7.37Hz,2H,–C H 2CH 2SO 3À),2.80(t,J ¼7.37Hz,2H,–CH 2SO 3À),4.23(t,J ¼7.37Hz,2H,–C H 2N ]), 4.43(t,J ¼7.37Hz,2H,–CH 2N þ^),7.68(d,J ¼15.46Hz,1H,imidazolium-H),7.68(d,J ¼15.46Hz,1H,imidazo-lium-H),9.02(s,1H,imidazolium-H);13C NMR (D 2O,100MHz)d 24.2(s),30.4(s),36.7(s),42.8(s),58.8(s),59.3(s),61.0(s),133.9(s),134.2(s),147.0(s);HRMS found m /z 247.1112,calcd for C 10H 19N 2O 3S:M þH,247.1118.A mixture of 3-(1-butyl-1H -imidazol-3-ium-3-yl)propane-1-sulfo-nate (2.473g,10.0mmol)and trifluoromethanesulfonic acid (1.628g,10.85mmol)was heated to 150 C and stirred at the same temperature for 5h.After being allowed to cool to room temperature,the obtained ionic liquid was washed repeatedly with toluene (20ml Â5)and Et 2O (20ml Â5)to remove non-ionic residues,and dried under vacuum at room temperature to give 1-butyl-3-(3-sulfopropyl)-1H -imidazol-3-ium trifluoromethanesulfonate (1)(3.924g,99%).4.2.2.1-Butyl-3-(3-sulfopropyl)-1H-imidazol-3-ium trifluoromethanesulfonate (1)Yield 99%;IR (neat)3415(SO 3H),1566(C ]C),1227(SO),1170(SO),1030(SO)cm À1;1H NMR (D 2O,400MHz)d 0.92(t,3H,J ¼7.34Hz,Ph OH 7PhPh H +PhOHPhPh Ph -H +PhPhPh Ph O PhPhPh OO PhPhPh HO-H 2OPhPhOO Ph8PhPhPhPh O O2b Scheme 4.Proposed reaction mechanism for the formation of 8.PhOH MeMeO O +initial use 4aa (77), 5 (7)first reuse 4aa (77), 5 (7)second reuse 4aa (75), 5 (5)Product (%)aaYields of isolated productsScheme 5.Reuse of the Bro¨nsted acid ionic liquid catalyst 1.K.Funabiki et al./Tetrahedron 65(2009)7457–74637460C H3CH2CH2CH2),1.33(sext,2H,J¼7.34Hz,CH3C H2CH2CH2),1.87 (quint,J¼7.34Hz,CH3CH2C H2CH2), 2.34(quint,J¼7.34Hz,2H,–C H2CH2SO3À), 2.93(t,2H,J¼7.34Hz,–CH2SO3À), 4.22(t,2H, J¼7.34Hz,–CH2N]),4.38(t,2H,J¼7.34Hz,–CH2Nþ^),7.54(d, 1H,J¼9.42Hz,imidazolium-H),7.54(d,1H,J¼9.42Hz,imidazolium-H),8.82(s,1H,imidazolium-H);13C NMR(D2O,100MHz)d23.2(s),29.4(s),35.8(s),41.8(s),57.9(s),58.4(s),60.1(s),50.2(s),130.3(q, J¼317.9Hz),133.0(s),133.3(s),146.0(s);HRMS found m/z247.1123, calcd for C10H19N2O3S:MÀCF3SO3,247.1116.4.3.Typical procedure for the recyclable Bro¨nsted acid1-catalyzed direct carbon–carbon bond formation of1,3-dicarbonyl compounds with alcoholsA mixture of1-butyl-3-(3-sulfopropyl)-1H-imidazol-3-ium tri-fluoromethanesulfonate(1)(0.060g,0.151mmol),1-phenylethanol (3a)(0.370g,3.029mmol)and pentane-2,4-dione(2a)(1.503g, 15.01mmol)in1-ethyl-3-methyl-1H-imidazol-3-ium trifluorome-thanesulfonate(1ml)under argon was stirred at100 C for3h.The mixture was then cooled to room temperature and extracted from the ionic liquid with a mixed solvent of Et2O/hexane(1:1) (30mlÂ3).After the solvent was removed under reduced pressure, the product was purified by column chromatography on silica gel with hexane/EtOAc(20:1)to give3-(1-phenylethyl)pentane-2,4-dione(4aa)(0.478g,77%)and(E)-but-1-ene-1,3-diyldibenzene(5) (0.022g,7%).4.3.1.3-(1-Phenylethyl)pentane-2,4-dione(4aa)3aYield77%;Mp46.9–47.9 C(lit.43–45 C);R f0.38(hexane/ EtOAc¼5:1);IR(CHCl3)1697(C]O),1722(C]O)cmÀ1;1H NMR (CDCl3,400MHz)d1.16(d,J¼7.00Hz,3H,CHC H3),1.78(s,3H, COCH3),2.22(s,3H,COCH3),3.51–3.59(m,1H,C H CH3),3.99(d, J¼7.00Hz,1H,C H COCH3),7.13–7.26(m,5H,aryl H);13C NMR (CDCl3,100MHz)d21.6(s),30.4(s),30.5(s),41.1(s),77.4(s),127.7 (s),128.0(s),130.0(s),143.8(s),204.1(s),204.2(s);HRMS found m/z204.1151,calcd for C13H16O2:M,204.1154.4.3.2.(E)-But-1-ene-1,3-diyldibenzene(5)3aYield7%;R f0.38(hexane);IR(neat)1600(C]C)cmÀ1;1H NMR (CDCl3,400MHz)d1.38(d,J¼7.00Hz,3H,CHC H3),3.55(quint, J¼7.00Hz,1H,C H CH3),6.30–6.32(m,2H,2Âvinyl H),7.08–7.28(m, 10H,aryl H);13C NMR(CDCl3,100MHz)d21.4(s),42.7(s),126.3(s), 126.4(s),127.2(s),127.4(s),128.6(s),135.3(s),137.7(s),145.7(s); HRMS found m/z208.1259,calcd for C16H16:M,208.1253.4.3.3.1,10-Oxybis(ethane-1,1-diyl)dibenzeneYield33%;dr¼50:50;R f0.60(hexane/CH2Cl2¼1:1);1H NMR (CDCl3,400MHz)d1.31(d,6H,J¼6.52Hz,2ÂCHC H3),1.39(d,6H, J¼6.52Hz,2ÂCHC H3),4.18(q,2H,J¼6.52Hz,2ÂC H CH3),4.46(q, 2H,J¼6.52Hz,2ÂC H CH3),7.13–7.31(m,20H,aryl H);13C NMR (CDCl3,100MHz)d23.9(s),25.6(s),75.3(s),75.5(s),127.1(s),127.2 (s),128.0(s),128.3(s),129.1(s),129.4(s),145.0(s),145.1(s);MS(EI) m/z226(M,7.5%).4.3.4.4-Phenylpentan-2-one11Yield20%;R f0.29(hexane/CH2Cl2¼1:1);IR(neat)1716 (C]O)cmÀ1;1H NMR(CDCl3,400MHz)d1.29(d,3H,J¼7.00Hz, C H3CHPh), 2.09(s,3H,COCH3), 2.68(dd,1H,J¼7.00,16.18Hz, CH2CO), 2.78(dd,1H,J¼7.00,16.18Hz,CH2CO), 2.78(sext, J¼7.00Hz,1H,CH3C H Ph),7.20–7.35(m,5H,aryl H);13C NMR (CDCl3,100MHz)d21.9(s),30.5(s),35.3(s),51.9(s),126.2(s),126.6 (s),128.4(s),146.1(s),207.8(s);MS(EI)m/z162(M,34.3%).4.3.5.3-benzhydrylpentane-2,4-dione(4ab)3aYield94%;Mp114.9–116.1 C(lit.112–114 C);R f0.43(hexane/ CH2Cl2¼1:3);IR(CHCl3)1697(C]O),1719(C]O)cmÀ1;1H NMR (CDCl3,400MHz)d2.00(s,6H,2ÂCOCH3),4.81(d,J¼12.32Hz,1H,C H Ph),4.73(d,J¼12.32Hz,1H,C H COCH3),7.15–7.20(m,2H,aryl H),7.24–7.29(m,8H,arlyl H);13C NMR(CDCl3,100MHz)d30.5(s),52.1 (s),75.4(s),127.9(s),128.6(s),129.8(s),142.1(s),203.8(s);HRMS found m/z266.1308,calcd for C18H18O2:M,266.1307.4.3.6.(Z)-3-(1,3-Diphenylallyl)pentane-2,4-dione(4ac)1Yield90%;Mp83.0–83.8 C(lit.85 C);R f0.20(hexane/ Et2O¼5:1);IR(CHCl3)1682(C]O),1732(C]O)cmÀ1;1H NMR (CDCl3,400MHz)d1.92(s,3H,COCH3),2.25(s,3H,COCH3),4.30–4.37(m,2H,C H COCH3and CHPh),6.16–6.22(m,1H,PhCH]C H), 6.43(d,J¼15.70Hz,1H,PhC H]CH),7.20–7.33(m,10H,aryl H);13C NMR(CDCl3,100MHz)d30.4(s),30.7(s),49.8(s),127.0(s),127.9 (s),128.4(s),128.6(s),129.2(s),129.7(s),129.9(s),132.3(s),137.2 (s),140.7(s),141.9(s),203.4(s),203.5(s);HRMS found m/z 292.1475,calcd for C20H20O2:M,292.1464.4.3.7.(E)-3-(Pent-3-en-2-yl)pentane-2,4-dione(4ad)Yield47%;R f0.18(hexane/Et2O¼5:1);IR(neat)1698(C]O), 1722(C]O)cmÀ1;1H NMR(CDCl3,400MHz)d0.96(d,J¼7.19Hz, 3H,CHC H3),1.62(d,J¼7.19Hz,3H,C H3CH:CH),2.11(s,3H,COCH3), 2.19(s,3H,COCH3), 2.97(sext,J¼7.19Hz,1H,C H CH3), 3.56(d, J¼7.19Hz,1H,C H COCH3),5.19–5.25(m,1H,CH3CH]C H),5.46–5.55 (m,1H,CH3C H]CH);13C NMR(CDCl3,100MHz)d17.8(s),19.0(s), 29.5(s),30.0(s),37.7(s),75.8(s),126.4(s),132.3(s),204.0(s),204.0 (s);HRMS found m/z168.1158,calcd for C10H16O2:M,168.1151. 4.3.8.3-(1,3-Diphenylprop-2-ynyl)pentane-2,4-dione(4ae)3bYield88%;Mp95.4–96.0 C(lit.90–92 C);R f0.50(hexane/ CH2Cl2¼1:3);IR(CHCl3)1701(C]O),1733(C]O)cmÀ1;1H NMR (CDCl3,400MHz)d1.93(s,3H,COCH3),2.39(s,3H,COCH3),4.22(d, J¼10.87Hz,1H,C H Ph),4.67(d,J¼10.87Hz,1H,C H COCH3),7.25–7.42(m,10H,aryl H);13C NMR(CDCl3,100MHz)d28.7(s),31.1(s), 38.0(s),75.6(s),84.9(s),88.0(s),122.7(s),127.7(s),128.1(s),128.2 (s),128.3(s),128.9(s),131.6(s),138.2(s),201.6(s),201.6(s);HRMS found m/z290.1310,calcd for C20H18O2:M,290.1307.4.3.9.1,3-Diphenyl-2-(1-phenylethyl)propane-1,3-dione(4ba)3aYield81%;Mp126.1–126.8 C(lit.126–127 C);R f0.15(hexane/ EtOAc¼20:1);IR(KBr)1683(C]O),1733(C]O)cmÀ1;1H NMR (CDCl3,400MHz)d1.33(d,J¼7.00Hz,3H,CHC H3),4.03–4.11(m, 1H,C H Ph),5.63(d,J¼7.00Hz,1H,C H COPh),7.04(t,J¼7.35Hz,1H, aryl H),7.14(t,J¼7.35Hz,2H,aryl H),7.22–7.26(m,4H,aryl H), 7.35–7.42(m,3H,aryl H),7.52(t,J¼7.35Hz,1H,aryl H),7.73(d, J¼7.35Hz,2H,aryl H),8.02(d,J¼7.35Hz,2H,aryl H);13C NMR (CDCl3,100MHz)d20.5(s),41.5(s),65.0(s),126.9(s),128.0(s), 128.7(s),128.8(s),129.1(s),129.1(s),133.3(s),133.9(s),137.1(s), 137.4(s),144.1(s),194.9(s),195.3(s);HRMS found m/z328.1467, calcd for C23H20O2:M,328.1464.4.3.10.2-Benzhydryl-1,3-diphenylpropane-1,3-dione(4bb)12Yield98%;Mp221.6–222.3 C(lit.228.6–230.2 C);R f0.28 (hexane/CH2Cl2¼1:1);IR(KBr)1661(C]O),1683(C]O)cmÀ1;1H NMR(CDCl3,400MHz)d5.32(d,J¼11.71Hz,1H,C H COPh),6.35(d, J¼11.71Hz,1H,CHPh),7.05(t,J¼7.46Hz,2H,aryl H),7.15(t, J¼7.46Hz,4H,aryl H),7.24(s,4H,aryl H),7.33(t,J¼7.46Hz,4H,aryl H),7.47(t,J¼7.46Hz,2H,aryl H),7.83(d,J¼7.46Hz,4H,aryl H);13C NMR(CDCl3,100MHz)d52.4(s),62.3(s),126.6(s),128.3(s),128.5 (s),128.6(s),128.6(s),133.2(s),136.9(s),141.7(s),194.1(s);HRMS found m/z390.1618,calcd for C28H22O2:M,390.1621.4.3.11.Ethyl2-acetyl-3-phenylbutanoate(4ca)2bYield30%;R f0.63(hexane/EtOAc¼5:1);IR(neat)1717(C]O), 1747(C]O)cmÀ1;1H NMR(CDCl3,400MHz)d0.85(t,J¼7.10Hz, 3H,COOCH2C H3),1.16(d,J¼8.88Hz,3H,CHC H3),1.21(t,J¼7.10Hz, 3H,COOCH2C H3), 1.22(d,J¼8.88Hz,3H,CHC H3), 1.85(s,3H,K.Funabiki et al./Tetrahedron65(2009)7457–74637461COCH3),2.22(s,3H,COCH3),3.44–3.48(m,2H,PhCH),3.67(d, J¼8.88Hz,1H,C H COCH3),3.72(d,J¼8.88Hz,1H,C H COCH3),3.80(q, J¼7.10Hz,2H,COOC H2CH3),4.14(q,J¼7.10Hz,2H,COOC H2CH3), 7.11–7.21(m,10H,aryl H);13C NMR(CDCl3,100MHz)d13.7(s),14.2 (s),20.4(s),20.6(s),29.6(s),29.9(s),39.8(s),40.1(s),61.2(s),61.5 (s),67.0(s),67.6(s),76.8(s),77.1(s),77.4(s),126.8(s),126.9(s), 127.4(s),127.5(s),128.5(s),128.7(s),143.1(s),143.3(s),168.2(s), 168.6(s),202.4(s);HRMS found m/z234.1263,calcd for C14H18O3: M,234.1256.4.3.12.Ethyl2-benzhydryl-3-oxobutanoate(4cb)3aYield91%;Mp87.8–89.0 C(lit.84–86 C);R f0.38(hexane/ CH2Cl2¼1:1);IR(CHCl3)1716(C]O),1738(C]O)cmÀ1;1H NMR (CDCl3,400MHz)d1.00(t,J¼7.10Hz,3H,COOCH2C H3),2.09(s,3H, COCH3),3.98(q,J¼7.10Hz,2H,COOC H2CH3),4.52(d,J¼12.20Hz, 1H,CHPh),4.76(d,J¼12.20Hz,1H,C H COCH3),7.14–7.18(m,2H,arylH),7.23–7.30(m,8H,aryl H);13C NMR(CDCl3,100MHz)d13.4(s),29.7(s),50.5(s),61.2(s),64.9(s),126.5(s),126.6(s),127.4(s),127.5 (s),128.3(s),128.5(s),140.9(s),141.2(s),167.3(s),201.4(s);HRMS found m/z296.1419,calcd for C19H20O3:M,296.1413.Found:C, 76.91;H,6.87.C19H20O3requires C,77.00;H,6.80.4.3.13.(Z)-Ethyl2-acetyl-3,5-diphenylpent-4-enoate(4cc)7Yield76%;R f0.20(hexane/EtOAc¼20:1);IR(neat)1714(C]O), 1741(C]O)cmÀ1;1H NMR(CDCl3,400MHz)d0.93(t,J¼7.10Hz, 3H,COOCH2C H3),1.16(t,J¼7.10Hz,3H,COOCH2C H3),1.99(s,3H, COCH3),2.26(s,3H,COCH3),3.89(q,J¼7.10Hz,2H,COOC H2CH3),4.05(d,J¼10.99Hz,2H,C H COCH3), 4.08(d,J¼10.99Hz,2H,C H COCH3),4.12(q,J¼7.10Hz,2H,COOC H2CH3),4.26(t,J¼10.99Hz, 2H,CHPh),6.18–6.30(m,2H,PhCH]C H),6.39(d,J¼10.99Hz,1H, PhC H]CH),6.43(d,J¼10.99Hz,1H,PhC H]CH),7.12–7.29(m,20H, aryl H);13C NMR(CDCl3,100MHz)d13.3(s),13.7(s),29.4(s),29.5 (s),48.3(s),48.5(s),60.9(s),61.1(s),64.8(s),65.1(s),125.9 (s),125.9(s),126.6(s),126.7(s),127.1(s),127.1(s),127.5(s),127.5(s), 128.0(s),128.2(s),128.4(s),128.8(s),129.0(s),131.0(s),131.3(s), 136.2(s),136.3(s),139.7(s),139.9(s),167.1(s),167.4(s),200.9 (s),201.2(s);HRMS found m/z322.1574,calcd for C21H22O3:M, 322.1570.4.3.14.Ethyl2-acetyl-3,5-diphenylpent-4-ynoate(4ce)3bYield84%;R f0.50(hexane/EtOAc¼15:1);IR(neat)1719 (C]O),1746(C]O)cmÀ1;1H NMR(CDCl3,400MHz)d1.00(t, J¼7.06Hz,3H,COOCH2C H3),1.24(t,J¼7.06Hz,3H,COOCH2C H3), 1.97(s,3H,COCH3),2.39(s,3H,COCH3),3.95(q,J¼7.06Hz,2H, COOC H2CH3), 3.98(d,J¼10.69Hz,1H,C H COCH3), 4.04(d, J¼10.69Hz,1H,C H COCH3),4.22(q,J¼7.06Hz,2H,COOC H2CH3), 4.60(d,J¼10.69Hz,1H,CHPh),4.63(d,J¼10.69Hz,1H,CHPh), 7.20–7.42(m,20H,aryl H);13C NMR(CDCl3,100MHz)d13.8(s), 14.1(s),29.8(s),30.6(s),37.8(s),37.8(s),61.6(s),61.8(s),66.5 (s),66.8(s),84.1(s),84.7(s),88.2(s),88.5(s),122.8(s),123.1(s), 127.6(s),127.7(s),128.1(s),128.2(s),128.2(s),128.2(s),128.3 (s),128.6(s),128.7(s),131.6(s),138.2(s),138.3(s),166.8(s), 167.1(s),200.3(s),200.7(s);HRMS found m/z320.1413,calcd for C21H20O3:M,320.1415.4.3.15.Ethyl2-benzhydryl-3-oxopentanoate(4db)Yield89%;Mp87.8–88.1 C;R f0.38(hexane/CH2Cl2¼1:1);IR (KBr)1714(C]O),1747(C]O)cmÀ1;1H NMR(CDCl3,400MHz) d0.84(t,J¼7.25Hz,3H,COCH2C H3),0.97(t,J¼7.25Hz,3H, COOCH2C H3), 2.18–2.28(m,1H,COC H2CH3), 2.46–2.56(m,1H, COC H2CH3),3.90–4.01(m,2H,COOC H2CH3),4.56(d,J¼12.20Hz, 1H,CHPh),4.82(d,J¼12.20Hz,1H,C H COCH2CH3),7.11–7.32(m, 10H,aryl H);13C NMR(CDCl3,100MHz)d7.1(s),13.6(s),36.6(s), 50.7(s),61.2(s),64.0(s),126.6(s),126.7(s),127.5(s),127.7(s),128.4 (s),128.6(s),141.3(s),141.5(s),167.5(s),204.1(s);MS(EI)m/z292 (MÀH2O,19.3%).4.3.16.Ethyl2-benzhydryl-3-oxo-3-phenylpropanoate(4eb)11Yield97%;Mp137.0–137.5 C(lit.141.9–143.1 C);R f0.54(hex-ane/CH2Cl2¼1:1);IR(KBr)1682(C]O),1730(C]O)cmÀ1;1H NMR (CDCl3,400MHz)d0.93(t,J¼7.12Hz,3H,COOCH2C H3),3.85–3.99 (m,2H,COOC H2CH3),5.08(d,J¼11.83Hz,1H,CHCOPh),5.41(d, J¼11.83Hz,1H,CHPh),7.03–7.07(m,1H,arlyl H),7.12–7.30(m,7H, arlyl H),7.34–7.45(m,4H,arlyl H),7.53–7.57(m,1H,arlyl H),8.00–8.02(m,2H,arlyl H);13C NMR(CDCl3,100MHz)d13.7(s),50.9(s), 59.4(s),61.5(s),126.5(s),126.8(s),127.7(s),128.2(s),128.5(s), 128.6(s),128.6(s),128.7(s),133.5(s),136.6(s),141.7(s),167.7(s), 192.8(s);MS(EI)m/z340(MÀH2O,46.4%).4.4.Typical procedure for the recyclable Bro¨nsted acid1-catalyzed tandem direct benzylation,cyclization and dehydration of the alcohol3fA mixture of1-butyl-3-(3-sulfopropyl)-1H-imidazol-3-ium tri-fluoromethanesulfonate(1)(0.020g,0.050mmol),2-(hydroxy-(phenyl)methyl)phenol(3f)(0.199g,0.994mmol)and pentane-2,4-dione(2a)(0.503g,5.024mmol)in1-ethyl-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate(1ml)under argon was stirred at 100 C for3h.The mixture was then cooled to room temperature and extracted from the ionic liquid with a mixed solvent of Et2O/hexane (1:1)(30mlÂ3).After the solvent was removed under reduced pressure,the product was purified by column chromatography on silica gel with hexane/CH2Cl2(1:4)to give1-(2-methyl-4-phenyl-4H-chromen-3-yl)ethanone(6af)(0.204g,77%).4.4.1.1-(2-Methyl-4-phenyl-4H-chromen-3-yl)ethanone(6af)Yield77%;R f0.58(hexane/CH2Cl2¼1:4);IR(neat)1682 (C]O)cmÀ1;1H NMR(CDCl3,400MHz)d2.13(s,3H,COCH3),2.43 (s,3H,CCH3),4.99(s,1H,CHPh),6.92–6.99(m,2H,aryl H),7.06–7.14 (m,3H,aryl H),7.19–7.30(m,4H,aryl H);13C NMR(CDCl3,100MHz) d20.5(s),30.5(s),42.6(s),114.5(s),116.7(s),124.9(s),125.2(s), 127.2(s),127.9(s),128.0(s),129.3(s),129.3(s),146.2(s),149.4(s), 159.5(s),199.2(s);HRMS found m/z264.1147,calcd for C18H16O2: M,264.1151.4.4.2.(2,4-Diphenyl-4H-chromen-3-yl)(phenyl)methanone(6bf)Yield98%;Mp152.5–153.0 C;R f0.30(hexane/CH2Cl2¼2:1);IR (KBr)1643(C]O)cmÀ1;1H NMR(CDCl3,400MHz)d5.35(s,1H, CHPh),7.02–7.19(m,9H,aryl H),7.22–7.28(m,4H,aryl H),7.36–7.39 (m,2H,aryl H),7.43–7.51(m,4H,aryl H);13C NMR(CDCl3,100MHz) d43.9(s),114.4(s),116.5(s),124.6(s),126.7(s),127.6(s),127.8(s), 127.9(s),128.1(s),128.6(s),129.1(s),129.3(s),129.5(s),129.7(s), 131.7(s),133.3(s),138.4(s),145.2(s),150.3(s),155.3(s),197.2(s); HRMS found m/z388.1471,calcd for C28H20O2:M,388.1464.4.4.3.Ethyl2-methyl-4-phenyl-4H-chromene-3-carboxylate(6cf)9Yield84%;R f0.75(hexane/CH2Cl2¼1:4);IR(neat)1710 (C]O)cmÀ1;1H NMR(CDCl3,400MHz)d1.16(t,J¼7.12Hz,3H, COOCH2C H3),2.51(s,3H,CCH3),4.02–4.15(m,2H,COOC H2CH3),5.04(s,1H,CHPh),6.94–6.98(m,1H,aryl H),7.00–7.06(m,2H,arylH),7.09–7.15(m,2H,aryl H),7.20–7.24(m,4H,aryl H);13C NMR (CDCl3,100MHz)d13.6(s),19.0(s),41.0(s),59.6(s),105.6(s),115.7 (s),124.0(s),124.3(s),125.9(s),127.0(s),127.3(s),127.9(s),128.7 (s),146.2(s),148.8(s),159.5(s),166.6(s),HRMS found m/z 294.1265,calcd for C19H18O3:M,294.1256.4.4.4.Ethyl2-ethyl-4-phenyl-4H-chromene-3-carboxylate(6df)Yield80%;R f0.50(hexane/CH2Cl2¼1:1);IR(neat)1703 (C]O)cmÀ1;1H NMR(CDCl3,400MHz)d1.17(t,J¼7.30Hz,3H, CCH2C H3),1.29(t,J¼7.30Hz,3H,COOCH2C H3),2.84–3.00(m,2H, CC H2CH3),4.02–4.15(m,2H,COOC H2CH3),5.03(s,1H,CHPh),6.94–6.98(m,1H,aryl H),7.02–7.07(m,2H,aryl H),7.10–7.16(m,2H,arylH),7.21–7.23(m,4H,aryl H);13C NMR(CDCl3,100MHz)d11.9(s),K.Funabiki et al./Tetrahedron65(2009)7457–7463 7462。

1.Beckmann 重排肟在酸如硫酸、多聚磷酸以及能产生强酸的五氯化磷、三氯化磷、苯磺酰氯、亚硫酰氯等作用下发生重排，生成相应的取代酰胺，如环己酮肟在硫酸作用下重排生成己内酰胺：反应机理：在酸作用下，肟首先发生质子化，然后脱去一分子水，同时与羟基处于反位的基团迁移到缺电子的氮原子上，所形成的碳正离子与水反应得到酰胺。

迁移基团如果是手性碳原子，则在迁移前后其构型不变，例如：2. Birch还原反应实例3.Cannizzaro 反应4.反应实例4. Chichibabin反应反应实例吡啶类化合物不易进行硝化，用硝基还原法制备氨基吡啶甚为困难。

本反应是在杂环上引入氨基的简便有效的方法，广泛适用于各种氮杂芳环，如苯并咪唑、异喹啉、吖啶和菲啶类化合物均能发生本反应。

5. Claisen酯缩合反应二元羧酸酯的分子内酯缩合见Dieckmann 缩合反应。

反应机理反应实例6. Claisen重排烯丙基芳基醚在高温(200°C)下可以重排，生成烯丙基酚。

当烯丙基芳基醚的两个邻位未被取代基占满时，重排主要得到邻位产物，两个邻位均被取代基占据时，重排得到对位产物。

对位、邻位均被占满时不发生此类重排反应。

交叉反应实验证明：Claisen重排是分子内的重排。

采用 γ-碳 14C 标记的烯丙基醚进行重排，重排后 γ-碳原子与苯环相连，碳碳双键发生位移。

两个邻位都被取代的芳基烯丙基酚，重排后则仍是α-碳原子与苯环相连。

芳环上取代基的电子效应对重排无影响。

取代的烯丙基芳基醚重排时，无论原来的烯丙基双键是Z-构型还是E-构型，重排后的新双键的构型都是E-型，这是因为重排反应所经过的六员环状过渡态具有稳定椅式构象的缘故。

反应实例Claisen 重排具有普遍性，在醚类化合物中，如果存在烯丙氧基与碳碳相连的结构，就有可能发生Claisen 重排。

7. Clemmensen还原醛类或酮类分子中的羰基被锌汞齐和浓盐酸还原为亚甲基：此法只适用于对酸稳定的化合物。

黄鸣龙还原反应是第一个以中国人姓名命名的反应，在国际上已广泛应用。

本书是一本汇集国内外关于黄鸣龙还原反应应用的成就、经过分析整理撰写而成的具有创见性的新著作。

书中系统介绍了黄鸣龙还原反应的发展历史、反应机理、应用范围和还原实例，是对黄鸣龙教授原始遗作及其有关工作的首次总结，可供有机化学专业的学生、科研人员及有机合成工作者学习和参考。

1911年，俄国化学家Nikolai Kishner将液体腙类化合物逐滴加到镀铂的多孔板与KOH混合体系中，加热后（约200 ℃）可消除N2得到相应的烷烃产物。

一年以后，德国化学家Ludwig Wolff又发现，将缩氨基脲溶于乙醇中，并加入乙醇钠作为碱，得到的乙醇溶液置于封管中加热至180 ℃，反应经历腙中间体，最终同样得到烷烃产物。

由于醛、酮等羰基化合物可与肼（NH2NH2）、氨基甲酰肼缩合制备相应的腙与缩氨基脲，所以这两种方法可用于羰基化合物脱氧还原。

这样的反应过程便叫作Wolff-Kishner还原（Wolff-Kishner Reduction）反应。

无论是Nikolai Kishner先生还是Wolff先生发展的方法，反应均需在封管、高压釜等密闭条件下进行，不仅操作不方便，反应过程中还会产生N2，体系压力过大则存在安全隐患。

为此，人们对这种方法的反应条件进行了改进：将醛、酮等羰基化合物溶于高沸点溶剂（如乙二醇、丙三醇）中，并加入NH2NH2与过量的碱（如金属钠、NaOEt），体系加热至回流状态。

此时反应的产率得到明显的提高，也无需在压力体系下进行。

但这种反应体系同样存在缺点，其中一个问题便是羰基化合物与NH2NH2缩合会形成水，由此导致体系温度降低，反应时间大大延长，一般需要加热反应50-100 h；除此之外，水会额外消耗一部分碱，因而体系中需要加入过量的碱与大量的溶剂。

1946年，中国化学家黄鸣龙对这一过程进行了改进，羰基化合物与NH2NH2缩合后形成相应的腙中间体，随后蒸馏除去形成的水与剩余的NH2NH2，此时不再需要大量的溶剂，体系规模也可进一步缩小。

卤氨化反应英语Here is an English essay on the topic of "Halogenation Reactions" with a word count of over 600 words:Halogenation reactions are a fundamental class of organic chemical transformations that involve the introduction of a halogen atom, such as chlorine, bromine, or iodine, into an organic compound. These reactions are of great importance in organic synthesis, as they provide a means to functionalize and modify organic molecules, leading to the creation of new and useful compounds.One of the most common types of halogenation reactions is the electrophilic halogenation of alkenes. In this process, an alkene, which is a carbon-carbon double bond, reacts with a halogen molecule (e.g., Cl2, Br2, or I2) to form a haloalkane, also known as an alkyl halide. The mechanism of this reaction typically involves the initial formation of a bromonium or chloronium ion intermediate, followed by the attack of a nucleophile, such as a halide ion, to displace the halogen and form the final product.For example, the reaction of ethene (C2H4) with bromine (Br2) would proceed as follows:C2H4 + Br2 → CH2Br-CH2Br (1,2-dibromoethane)The bromonium ion intermediate is formed first, and then the bromide ion attacks to displace one of the bromine atoms, resulting in the formation of 1,2-dibromoethane.Another important class of halogenation reactions is the radical halogenation of alkanes. This process involves the use of a radical initiator, such as ultraviolet light or peroxide, to generate a halogen radical, which then abstracts a hydrogen atom from the alkane to form a new alkyl radical. This alkyl radical then combines with another halogen molecule to produce the haloalkane product.For example, the reaction of methane (CH4) with chlorine (Cl2) under radical conditions would proceed as follows:CH4 + Cl· → CH3· + HClCH3· + Cl2 → CH3Cl + Cl·The initial chlorine radical abstracts a hydrogen atom from methane, forming a methyl radical, which then combines with another chlorine molecule to give chloromethane (CH3Cl).Halogenation reactions can also be used to functionalize morecomplex organic molecules, such as aromatic compounds. In these cases, the halogenation typically occurs through an electrophilic aromatic substitution mechanism, where the halogen electrophile replaces a hydrogen atom on the aromatic ring.For instance, the reaction of benzene (C6H6) with bromine (Br2) in the presence of a Lewis acid catalyst, such as FeBr3, would produce bromobenzene (C6H5Br):C6H6 + Br2 (FeBr3) → C6H5Br + HBrThe Lewis acid catalyst helps to activate the bromine molecule, facilitating the electrophilic substitution on the aromatic ring.Halogenation reactions have a wide range of applications in organic synthesis, including the preparation of various pharmaceutical intermediates, agrochemicals, and other valuable organic compounds. Furthermore, the halogenated products can serve as useful building blocks for further chemical transformations, allowing for the synthesis of more complex molecules.In conclusion, halogenation reactions are a versatile and essential tool in the field of organic chemistry, enabling the introduction of halogen atoms into organic compounds and facilitating the creation of a diverse array of useful and often complex chemical structures.。

磷自由基的偶联反应研究英文回答：The study of the coupling reactions of phosphorus radicals is an important area of research in organic chemistry. Phosphorus radicals are highly reactive species that can undergo various types of reactions, including radical-radical coupling reactions. These reactions involve the formation of a new bond between two phosphorus radicals, resulting in the formation of a dimeric product.One approach to studying the coupling reactions of phosphorus radicals is through the use of spectroscopic techniques. For example, electron paramagnetic resonance (EPR) spectroscopy can be used to detect and characterize phosphorus radicals in solution. By monitoring the changesin the EPR spectrum upon addition of a coupling agent, information about the reaction mechanism and the nature of the dimeric product can be obtained.Another method for studying the coupling reactions of phosphorus radicals is through the synthesis and characterization of model compounds. These model compounds are designed to mimic the reactivity of phosphorus radicals and can be used to gain insights into the factors that influence the coupling reactions. For example, the effect of different substituents on the reactivity and selectivity of the coupling reactions can be investigated using model compounds.In addition to spectroscopic and synthetic approaches, computational methods can also be employed to study the coupling reactions of phosphorus radicals. Quantum chemical calculations can provide valuable information about the reaction energetics, transition states, and reaction pathways. By comparing the calculated results with experimental data, the reliability of the proposed reaction mechanism can be assessed.Overall, the study of the coupling reactions of phosphorus radicals is a complex and challenging area of research. It requires a combination of experimental andcomputational techniques to fully understand the reaction mechanisms and to develop new strategies for selective and efficient synthesis of dimeric products.中文回答：磷自由基的偶联反应研究是有机化学中的一个重要领域。

摘要本文研究了不同保鲜剂对洋桔梗切花瓶插寿命及形态指标、生理指标的影响,以期筛选出能延长其瓶插寿命的保鲜剂。

结果表明,3%蔗糖+50mg/L 硫酸铝+0.1%柠檬酸+300mg/L 8-HQ 保鲜效果最为明显,洋桔梗瓶插寿命达到了13d 。

该处理花瓣中可溶性糖含量和可溶性蛋白质含量增加,游离脯氨酸含量和细胞膜透性下降,可有效延缓切花衰老。

在瓶插期间,洋桔梗切花的呼吸强度有突然升高后降低的现象,推断洋桔梗属呼吸跃变型花卉。

关键词洋桔梗;保鲜剂;瓶插寿命;形态指标;生理指标中图分类号S682.19文献标识码A 文章编号1007-5739(2022)13-0080-05DOI :10.3969/j.issn.1007-5739.2022.13.020开放科学(资源服务)标识码(OSID ):Preservation Effects of Different Preservatives on Eustoma grandiflorum Cut FlowerJIANG Yueli SHI Jinlin DU Xiuhong DONG Shaohui LI Junping(Yuxi Agriculture Vocation-Technical College,Yuxi Yunnan 653106)Abstract The effects of different preservatives on the vase-life,morphological indexes and physiological indexes of Eustoma grandiflorum were studied in this paper,so as to select a preservative to prolong the vase-life of Eustoma grandi-florum .The results showed that the effect of 3%sucrose+50mg/L Al 2(SO 4)3+0.1%citric acid+300mg/L 8-HQ was most significant,and the vase-life of Eustoma grandiflorum was 13d.Meanwhile,the contents of soluble sugar and soluble protein in petals increased,and the contents of free proline and cell membrane permeability declined.It could effectively delay senescence of the cut flower.During the vase planting,the respiratory intensity of Eustoma grandiflorum increased suddenly and then decreased.Therefore,it infers that Eustoma grandiflorum belongs to the respiratory climacteric flower.Keywords Eustoma grandiflorum ;preservative;vase-life;morphological index;physiological index不同保鲜剂对洋桔梗切花的保鲜效果姜跃丽师进霖杜秀虹董绍辉李军萍(玉溪农业职业技术学院,云南玉溪653106)洋桔梗(Eustoma grandiflorum )又名草原龙胆,为龙胆科多年生草本观赏植物,茎直立灰绿色,卵状或长椭圆形叶对生,叶片灰绿色,原产于北美洲,是近年逐渐流行的一种高档切花。

第19卷　第3期催　化　学　报1998年5月V ol.19　N o.3Chinese Jour nal of Cataly sis M ay　1998钯-手性膦催化降冰片烯的不对称氢酯基化反应*周宏英侯经国陈　静吕士杰傅宏祥**汪汉卿(中国科学院兰州化学物理研究所,兰州730000)提　要　首次用P d(O A c)2-1,4∶3,6-双脱水-2,5-二(二苯基膦)-L-艾杜糖醇(DD PPI)-p-T sOH催化体系对降冰片烯进行了不对称氢酯基化反应,获得了较好的结果.考察了手性膦配体的结构以及磷原子与钯原子的摩尔比对反应的影响,发现在一个磷原子配位一个钯原子时,获得了较高的光学产率.同时考察了反应温度、反应压力及溶剂对降冰片烯不对称氢酯基化反应的影响,发现在120℃, 5.0M Pa,n(P)/n(Pd)=1时,化学产率可达71.6%,光学产率可达92.2%.关键词　降冰片烯,不对称氢酯基化反应,醋酸钯,手性膦催化剂分类号　O643/O 627不对称羰基化反应的研究近年来发展迅速,它是合成多种手性分子的有效途径[1].而这些手性分子是合成药物和农业化学品非常有价值的前体.不对称羰基化反应不仅涉及到对映体选择性,而且涉及到化学选择性(羰基化反应与副反应)和区域选择性(异构与正构).不对称羰基化反应包括不对称氢甲酰化反应、氢酯基化反应和氢羧基化反应.其中人们研究最广泛的是不对称氢甲酰化反应,而对氢酯基化反应的研究较少[2,3].由于氢酯基化反应的产物是羧酸酯,比氢甲酰化反应的产物醛要稳定,不易发生外消旋化,所以此类反应的研究已经引起了人们的兴趣.Botteghi等[4]首次报道了用PdCl2-(-)DIOP催化烯烃的氢酯基化反应.此后,人们对不对称氢酯基化反应做了很多尝试[5～9],企图得到高的光学收率.Apler等[10]用PdCl2-BNPPA催化剂体系研究了6-甲氧基萘乙烯的氢羧基化反应,得到了91%ee的光学产率,并且有较高的化学产率.对环烯的不对称羰基化反应的研究主要集中在氢甲酰化反应[11],但是所得的光学产率都较低,最高不超过30%.我们用Pd(OAc)2-手性膦-p-T sOH催化剂体系对降冰片烯进行不对称氢酯基化反应,得到了高的光学产率和较好的化学产率(反应(1)).另外在这个反应中存在着一个副反应(反应(2)).收稿日期:1997-06-05.　周宏英:男,1967年生,博士,副研究员.*国家自然科学基金(批准号29473144)和中国石化总公司石油化工科学研究院资助项目.**通讯联系人.1　实验部分1.1　原料和试剂　乙醇,甲醇均为天津市化学试剂二厂生产,分析纯.对甲苯磺酸(p -T sOH ,含有1mol 的结晶水),北京西中化工厂生产,分析纯.降冰片烯,Aldrich Chemical Com pany Inc 生产.Pd (OAc )2自制.一氧化碳,本所自制(木炭电弧法).手性膦配体1,4∶3,6-双脱水-2,5-二(二苯基膦)-L -艾杜糖醇(DDPPI)是以甘露醇为原料合成的[12].1.2　催化反应　反应在内径1.6cm ,高13.5cm 的高压不锈钢反应器(25ml)中进行.向反应器中加入5.0ml 的溶剂甲醇,Pd(OAc)20.021mm ol,降冰片烯10.6mm ol,DDPPI 0.011mmo l,密闭反应器.在Schlenk 操作中室温下用CO 将反应体系置换三次,充入CO,压力升至指定数值停止进气.将反应器置于带搅拌的反应装置上,在指定的反应温度下恒温24h.反应结束后,记录压降,冷却反应器至室温,放空剩余的气体,打开反应器,取出反应液进行分析.1.3　产物分析　反应产物用SP -1102型气相色谱仪进行分析,使用SE -54型毛细管柱,柱长22.5m ,内径0.27m m,柱温140℃,氢火焰离子化检测器,归一化法定量.色谱给出的数据均是摩尔百分数.光学产率的分析用美国W ater 公司的高压液相色谱仪,手性填充柱CT B-10,150×4.6m m,I.D.6 m ,流动相V (正己烷)∶V (异丙醇)=98∶2.手性柱的固定相是纤维素-三(苯甲酸酯),产物经过减压蒸馏后再进入高压液相色谱仪分析.计算公式如下:ee =A R -A S A R +A S×100%A 为色谱峰面积.旋光仪为日本J AS COJ -20C 型自动记录仪.表1　P /Pd 摩尔比对降冰片烯不对称氢酯基化反应的影响T able 1　T he effect of P /P d mo lar r atio on the asymmet ric hy dr oester ificat ion o f no rbo rnene n (L *)/n (P d (OAc )2)Conversion (%)Yield 1)(%)EsterEther Optical yield 2)(%)Configuration 3)399.687.012.645.31S,2S,4R 299.988.611.241.91S ,2S ,4R 198.986.912.023.21S ,2S ,4R 0.599.176.822.369.81S ,2S ,4RReaction conditions :Pd (OAc )20.021mmol ,Norbornene 10.6m mol ,M eth anol 5.0ml ,Reaction tem -peratu re 120℃,Pressu re 6.0M Pa ,Reaction time 24h .1)Yield b as ed on olefin .2)Determined by HPLC an alysis w ith a ch iral s tationary phas e column (Cellu -los e tribenzoate)after distillation under r educed pres sure.3)Determin ed by the s igns of optical rotation.2　结果与讨论2.1　n (P )/n (Pd )对降冰片烯不对称氢酯基化反应的影响　以甲醇为溶剂,降冰片烯在Pd -(OAc )2-手性膦-p -Ts 原位生成的催化剂体系存在下,与CO 反应生成两个非对映体ex o -2-降冰片烷基甲酸甲酯和endo -2-降冰片烷基甲酸甲酯,另外还有副产物2-甲氧基降冰片烷.手性配体的结构性质在烯烃的不对称氢化反应、氢甲酰化反应和氢酯基化反应中起着关键的作用.DDPPI 的分子结构表明这个双膦配体是一个刚性很好的双环化合物,并且有四个手性碳原子,它们的构型都是S 型.两个磷原子虽都在双环骨架的同一侧,但各朝一方,且它们之间还被两个氢原子隔开,因此不可能与单个的金属或离子螯合.此外,两个环中各有一个杂原子氧,也许可与反应底物分子的某部位有相互吸引或排斥作用.为此我们考察了手性配体DDP-PI 与Pd(OA c)2的摩尔比对降冰片烯不对称氢酯基化反应的影响,其结果列于表1(表中的构型用旋光仪测定,再与标准化合物的旋光相比而得).从表1结果可知,当L */Pd(OAc)2的摩248催　化　学　报19卷尔比为0.5时,也就是P/Pd 的摩尔比为1时,可以得到较高的光学产率.这是因为DDPPI 是一个非螯合型的双膦配体,在配位过程中是一个磷原子配位一个钯原子,所以这个双膦配体在钯催化降冰片烯的不对称氢酯基化反应中充当了一个单齿配体,这符合一般烯烃的不对称氢酯基化反应的规律[5,6].但L */Pd(OAc)2的摩尔比为0.5时,化学产率较低.2.2　反应压力对降冰片烯不对称氢酯基化反应的影响　当保持L */Pd(OAc)2的摩尔比为0.5时,其他反应条件不变,反应压力对降冰片烯不对称氢酯基化反应的影响结果列于表2.从表2可以看出,当反应压力从5.0MPa 升至7.0M Pa 时,产物的光学产率随着压力的升高而降低,化学产率随着压力的升高而增加.在反应压力为5.0M Pa 时可以得到最高的光学产率92.2%.表2　反应压力对降冰片烯的不对称氢酯基化反应的影响T able 2　T he effect o f pressur e o n the asy mmetr ic hydro est erificatio n o f nor bo r nenePres sure (M Pa )Conversion (%)Yield (%)Ester Ether Optical yield (%)Configuration 5.098.971.627.392.21S ,2S ,4R 6.099.176.822.369.81S ,2S ,4R 7.098.977.821.137.61S ,2S ,4RReaction cond itions :S am e as s how n in T able 1,but th e n (P)/n (Pd)=1and th e pres sure varied.2.3　反应温度对降冰片烯不对称氢酯基化反应的影响　当反应温度从100℃升到140℃时,降冰片烯的不对称氢酯基化反应的结果列于表3.表中数据表明,当反应温度为100℃时,获得了最高的光学产率.随后产物酯的光学产率随着反应温度的升高而降低,也就是说高温不利于烯烃的不对称氢酯基化反应,这与烯烃不对称氢甲酰化反应相同[13].表3　反应温度对降冰片烯的不对称氢酯基化反应的影响T able 3　T he effect o f temperat ur e on the asy mmetr ic hydro est erificatio n o f nor bo r nenet /℃Conversion (%)Yield (%)Ester Ether Optical yield (%)Configuration 10097.876.421.488.41S,2S,4R 11099.381.517.881.41S,2S,4R 12099.176.822.369.81S,2S,4R 13099.675.524.165.61S,2S,4R 14099.060.738.365.31S,2S,4RReaction cond itions :S am e as s how n in T able 1,but th e n (P )/n (Pd )=1and th e temperatur e varied .2.4　甲醇与乙醇对降冰片烯不对称氢酯基化反应的影响　不对称氢酯基化反应产物的光学产率在一定程度上也受到醇的影响,其结果见表4.在这个反应中,醇不仅可用作溶剂,也可以用作反应物.当用乙醇代替甲醇进行不对称氢酯基化反应时,光学产率从69.8%下降到53.1%.这种现象可解释为甲醇极性比乙醇大,很容易与降冰片烯进行不对称氢酯基化反应.而乙醇的极性比甲醇的小,在反应中形成酯的速度较慢,可能导致产物的消旋化.表4　不同的溶剂对降冰片烯的不对称氢酯基化反应的影响T able 4　T he asym metric hy dr oester ifica tio n o f nor bo rnene in methanol and et hano lSolvent (5.0ml)Conversion (%)Yield (%)Ester Ether Optical yield (%)Configuration M ethanol99.176.822.369.81S,2S,4R Ethanol 98.278.319.153.11S,2S,4RReaction cond itions :S am e as s how n in T able 1,but th e n (P)/n (Pd)=1and th e solvent varied.结论: 1.首次用Pd(OAc)2-1,4∶3,6-双脱水-2,5-二(二苯基膦)-L -艾杜糖醇-p -T sOH 催化体系对降冰片烯进行了不对称氢酯基化反应,获得了较好的结果. 2.对手性配体的结构以及磷原子与钯原子的摩尔比对反应的影响进行了考察,发现在一个磷原子配位一个钯原子2493期周宏英等:钯-手性膦催化降冰片烯的不对称氢酯基化反应250催　化　学　报19卷时,获得了较高的光学产率. 3.反应温度、反应压力及溶剂对降冰片烯的不对称氢酯基化反应影响较大,当反应温度为120℃,压力为5.0M Pa,n(P)/n(Pd)=1时,化学产率可达71.6%,光学产率可达92.2%.参考文献1　T katchenko I,V illeur banne C N R S.I n:Wilkinson S G ed.Co mpr ehensive Or g ano metallic Chemist ry, V o l8.N ew Yo rk:Per gamo n,1982.1012　N o yo ri R.A symmet ric Cata ly sis in Or ganic Sy nthesis.N ew Y o rk:Jo hn W iley,1993.1623　Beller M,Co rnils B,K ohlpaintner C W et al.J M ol Catal A:Chemical,1995,104:174　Bot teghi C,Consig lio G,Pino P.Chimia,1973,27:4775　Hay ashi T,T anaka M,Og ata I.T etrahedr on L ett,1978,39256　Becker Y,Eisenstadt A,Stille J K.J Or g Chem,1980,45:21457　Co nsiglio G.J Or ganomet Chem,1977,132:C268　Co metti G,Chiusoli G P.J Or ganomet Chem,1982,236:C319　A pler H,Hamel N.J Chem S oc,Chem Commun,1990,13510　A pler H,Hamel N.J A m Chem Soc,1990,112:280311　K ollar L,W ada T,L autens M.T etr ahedr on:A sy mmetry,1992,3:101112　Bako s J,Heil B,M arko L.J Or ganomet Chem,1983,253:24913　A gbossou F,Car pentier J F,M o rtr eux A et al.Chem R ev,1995,95:2485ASYMMETRIC HYDROESTERIFICATION OF NORBORNENE C ATALYZED BY CHIRAL NON-C HELATE BIPHOSPHINE-PALLADIUM C OMPLEXESZhou Hongy ing,Ho u Jingguo,Chen Jing,L Shijie,Fu Hongx iang,W ang Hanqing(L anz hou I nstitute of Chemical Phy sics,T he Chinese A cademy of S ciences,L anz hou730000) Abstract　Hydroesterif icat ion and hydroformylation reactions of olefins cat-alyzed by met al complex are ex tensively investigat ed in homogeneous catalyt ic process.The asymmet ric hydroesterification of norbornene using palladium ac-et ate,1,4∶3,6-dianhydro-2,5-bis(diphenylpho sphino)-L-idit ol(DDPPI)and p-toluenesulfonic acid(p-T sOH)catalyt ic system under mild reaction conditions w as studied.The nature of DDPPI plays an important role in asymmet ric hy-droest erificat ion of norbornene.Ex perimental results show that DDPPI is an ef-fect ive chiral ligand for hydroesterification of norbornene.T he higher opt ical yield w as obt ained w hen the P/Pd molar rat io w as kept at1∶1.Ef fect of the re-act ion temperature,pressure,and solvent on asymmetric hy droest erificat ion of norbonene has also been invest igated w ith this catalyst syst em.Optical yield up to92.2%and g ood chemical yield71.6%are obtained under5.0M Pa,120℃, and n(P)/n(Pd)=1.Key words　N orbornene,Asymmet ric hydroesterification,Palladium acet at e, Chiral phosphine cat alyst system(Ed WWQ)。

让人尖叫的实验作者：王海萍来源：《课堂内外(初中版)》2013年第12期超长篇动漫《名侦探柯南》中有一个身着大褂的阿笠博士，他总是在摆满铁架台、酒精灯、漏斗和烧杯等各色实验器材的桌子前拿着试管将蓝蓝绿绿的液体左倾右倒，时而电闪雷鸣，时而烟雾缭绕，像神一样调制出一堆神奇药剂。

不过当你走进真的化学实验室，什么氧化铁和稀盐酸反应，碳酸钙沉淀反应，就远没有那么酷。

真实的化学实验有神奇之处吗？其实有的，只是我们通常见不到。

法老之蛇——硫氰酸汞燃烧膨胀反应2013年蛇年将至之时，著名的“法老之蛇（Pharaoh'ssnake）”因一个化学实验视频走红网络，不知情的人以为是哪个导演为喜迎蛇年拍摄的科幻贺岁片。

事实上，那既不是贺岁大片，也不是什么通灵术，只是一个膨胀反应。

实验中的硫氰酸汞（Hg（SCN）2）接触到足够的热源时，会发生陕速的放热反应，产生大量如蛇一样蜷曲的固体，所以被称为“法老之蛇”。

硫氰酸汞在燃烧时有蓝色、黄色或橙色的不明显火焰，形成的固体产物颜色从深灰色到浅棕色不等。

硫氰酸汞曾被用在爆竹制造中，但后来发现硫氰酸汞燃烧时产生剧毒物质，且硫氰酸汞本身也有毒，所以这种爆竹被禁售。

可见，化学实验在给我们带来神奇的艺术和震撼的视觉效果的同时，也附带一定的危险性。

黑暗之柱——白糖脱水实验白糖是日常生活中常用的食材，蜜汁又烧、糖醋排骨等美食的烹制都少不了它，北京城里著名的小吃“冰糖葫芦”也是没它不行。

白糖也能用来做化学实验吗？当然！我们在一个烧杯中投入5克白糖，然后再滴入几滴浓硫酸。

这时，我们就会看到白糖的颜色逐渐变黑，体积也迅速增大，犹如发糕一样“发”了起来。

真有意思，奥妙在哪呢？原来，白糖是一种碳水化合物，而浓硫酸又具有很强的脱水性，当二者相遇时，白糖分子中的水被硫酸夺走，经“脱水”后的白糖只剩下炭，所以变成了黑色。

白糖剩下的一部分碳又被浓硫酸氧化，生成了二氧化碳等气体跑出来，使混合物体积膨胀起来，就成了黑色的“发糕”。

高中生物学新课程标准教学研讨“种群和群落”的教学构思高中生物学新课程标准教学研讨“种群和群落”的教学构思生物学通报2007年第42卷第11期高中生物学新课程标准教学研讨种群和群落"的教学构思王冬梅苏明学(北京师范大学良乡附属中学北京102488) 在普通高中《生物课程标准》的内容标准中,"稳态与环境"模块的第4,第6学习单元,将在群体水平上探讨生物与环境的关系.包括种群生态学,群落生态学和生态系统生态学的相关内容.从而揭示宏观领域的稳态及其调节规律.其中,"种群和群落"单元是开篇之目.本文试探讨课程标准指导下的单元具体内容标准,教学目标及其教学策略.1解读具体内容标准1.1关于内容标准含义的讨论在《标准》中,"种群和群落"单元的具体内容标准及活动建议如下: 具体内容标准活动建议1)列举种群的特征1)探究培养液中酵母菌种群数量的动态变 2)尝试建立数学模型解2)土壤中动物类群丰富度的研究释种群的数量变动3)描述群落的结构特征3)调查当地自然群落中若干种生物的生态位 4)阐述群落的演替4)探究水族箱(或鱼缸)中群落的演替 1)列举属于了解水平的认知要求."列举种群的特征"要求学生能对种群密度,出生率和死亡率,迁入率和迁出率,年龄组成和性别比例等特征形成感性认识.感性认识的形成往往来自直觉和体验,因此,教学中应考虑让学生亲自参与一定的生态调查活动和学习生态学研究方法.如种群密度的调查法. 2)尝试属于模仿水平的技能性要求,解释属于理解水平的认知要求."尝试建立数学模型解释种群的数量变动"有3重含义:一是通过实验探究形成具体认识, 例如研究培养液中酵母菌种群数量的动态变化,记录数据,建立坐标系,描绘曲线图.二是尝试建立种群数量动态的数学模型.三是能说明种群增长的"J"型曲线和 "S"型曲线的含义并会应用.因此,探究性实验研究和跨学科综合是这部分认知活动的显着特征.3)描述属于了解水平的认知要求."描述群落的结构特征"包括2个方面:一是通过实地调查和资料分析, 了解群落的外貌特征及物种组成,如丰富度,优势种, 不同物种在自然群落中的生态位及其之间的相互关系等.二是能描述不同群落的垂直结构与水平结构. 4)阐述属于理解水平的认知要求."阐述群落的演替"要求能举例说明群落演替的概念及其类型,并正确理解地球现存的群落大都处于顶级状态. 5)通过学习逐渐内化种群,群落等概念,为揭示种群,群落,生态系统概念之间的内在联系奠定基础, 习得相关的研究方法,形成正确的生态学观点. 1.2关于教学地位与教育意义的认识种群既是物种的存在单位,也是物种繁殖和进化的单位.种群生态学是生态学研究中基础而重要的一个层次.认识群体水平的稳态,要从认识种群开始.只有明确认识了种群的特征,动态及其影响因素,才能更好地理解与群落和生态系统等相关的知识.群落是占有一定空间的多种生物种群的集合体, 由生物群落及其非生物环境就构成了一个生态学功能系统(生态系统).因此,学习有关群落的内容,是学习种群与生态系统知识的重要承接.更为重要的是,群落为种群的稳定生存和繁殖提供了保障.由于不同种群通过在一定空间内彼此之间的相互作用.结果比一个种群单独存在时更加稳定.群落不断演替,并且可以达到最终的平衡状态.种群与群落离不开一定的时间和空间环境,所以,这部分内容所承载的"物种多样性","整体大于部分之和","生物适应并影响环境"等观点也是不言而喻的.学习种群特征,群落结构与群落演替等知识的过程中,离不开相应的调查与探究活动.学生通过参与方案设计,动手操作,建立模型等活动过程,获得亲身经历与体验,不但有助于提高其实验操作技能和科学探究能力,还能初步领悟系统分析,建立数学模型的思想与方法.2分析教学目标2.1认知目标1)能解释种群概念,列举种群特征.2)能说出种群密度的含义及其调查方法. 3)知道种群数量变化规律是种群研究的核心问题, 尝试建立数学模型,解释种群的数量变化. 4)能辨别种群的指数增长和逻辑斯蒂增长,分析影响种群数量变化的因素,举例说明环境容纳量. 5)准确表述群落的概念要素,知道群落特征的基本内涵:外貌特征,物种组成及结构特征.6)能列举森林,草原等群落的物种组成.包括丰富度,优势种,生态位等,并能辨别群落中不同物种之间的关系.7)能描述群落的水平结构与垂直结构.8)了解群落演替的概念,能区别原生和次生演替,举例说明顶级群落2.2能力目标1)能结合实际情况制订种群密度调查的计划并实施.2)能采用液体培养法培养酵母菌,会控制培养过2007年第42卷第11期生物学通报27 程中的各种条件,正确记录数据,用坐标纸描绘数量变化曲线.3)尝试做出假设.建立种群指数增长和逻辑斯蒂增长的数学模型.4)了解调查物种的丰富度的基本方法.能以小组为单位,制定计划,合作实施,从一个侧面研究土壤中小动物的丰富度.5)调查当地自然群落中若干种生物的生态位. 6)探究水族箱(或鱼缸)中群落的演替.2.3情感态度与价值观目标1)在阐述不同群落的结构特征中,使学生体会到在一定区域内生存的动物,植物,微生物的丰富性,体现物种多样性的观点.2)在描述不同种群形成特定的群落时.应突出种群通过彼此之间的相互作用,形成了比单独存在时更加稳定的状态,使学生建立整体大于部分之和的观点. 3)在讨论种群的分布,数量变化,以及群落的演替等一系列问题中.应使学生理解生物适应并影响环境这一重要观点的确切含义.并领悟人与自然和谐发展的意义4)通过了解我国人口状况,生物资源与现状.以及调查家乡的群落特征等.增强学生的爱国情感与环境保护的责任感.5)指导学生运用相关的生态学知识和观念参与社会事务的讨论,将理论学习与社会实际,区域发展相结合,培养学生运用生态学原理分析解决实际问题.特别是解决一些环境问题的能力.3选择教学策略与方法3.1组织教学内容的依据1)"课程标准"和"标准解读"是教师组织教学内容的主要依据.教学内容必须体现"标准"的具体要求,教师不但要学习和领悟"课程标准"所提倡的基本理念,课程目标,内容标准和实施建议,还要注重学习和研究"标准解读"中的内容阐述,实施要点等. 2)教科书是施教的重要素材,但不是唯一素材. 教师应尽可能地提升自己研读教材,驾驭教材和反思教材的能力,摆脱被课本牵着鼻子走的误区,达到"用好课本"的水准.3)学生的学习基础和学习能力也是教师组织教学内容的重要依据.教学内容是为学生准备的,这一点十分重要.教学内容的组织应围绕着学生"学会"和"会学"这2个基本点来进行,了解学生的学习基础和学习能力需要提前进行调查和分析.4)学校周边的环境条件也可以充分利用.教师要充分调动一切可以利用的教学资源,保证教学内容的科学性,可行性和实用性.3.2教学的策略与方法3.2.1关于"种群"的教学1)关于种群概念的形成.教学活动可以按"给出定义一感知实例一归纳要点"的思路展开,诱导学生依据定义对例证做出肯定或否定的判断,并认识种群概念的3个要点:?生活在一定时间和空间内;?由同种生物个体组成;?是可以互相交配的群体.了解种群是物种的具体存在单位,繁殖单位和进化单位. 2)关于种群特征的归纳,可以引导学生按"调查研究一要素分析一把握重点"这一程序展开学习活动.?通过调查研究对种群形成初步的认知与体验. 教师应创造条件尽可能地让学生实地调查某种植物的种群密度,并根据具体的环境条件,以小组为单位制定方案,实施调查.通过调查活动使学生体验基本的研究方法,比如怎样确定调查对象?采用何种方法?怎样记录并计算种群密度?并讨论在调查中发现的有关问题.对于标志重捕法,可以通过讲解或利用模拟实验让学生感知.?分析要素是指领会种群的基本特征.归纳如下表:表1种群的基本特征基本特征具体要点种群的,——,/——,\/一,\口口口\簪簪,??,空问特征//……//…种群的I)种群内个体的全部基因构成一个种群基因库遗传特征2)种群内变异是物种进化的起点种群的数量特征??t篡?把握重点是指明确种群数量变化规律是种群研究的核心问题.归纳影响种群密度因素之间关系图解,使学生明确对种群数量动态具有决定作用的4个速率,以及预测种群发展趋势的主要结构因素. ll生\ 增长J(死芒/性别比例j测/一蔓f)种群密度!衰退',,,_\一酉lj决定种群消长的速率一,图1种群密度的决定性因素2007年第42卷第11期生物学通报教师还应引导学生对种群内部因素(生殖力等) 的影响做出分析,并将影响种群数量动态的内部与外部因素做出归纳.f生殖力(遗传性,内分泌调节等),内部阕素调节1I领域行为和迁移行为因素jf栖息空间和气候条件l【外部因素2食物和天敌}影响生殖(环境容纳量)I自然屏障——阻抑种群散布 ?讨论意义.种群增长模型的意义,在于它既是我们研究自然界各个种群动态(包括人口增长,生物入侵)问题的重要基础,也是在农业,林业,渔业等实践领域中,确定最大持续产量的主要模型. 3.2.2关于"群落"的教学群落生态学研究的主要内容归纳如下:丰富度优势种生态位1)群落概念的建立.可以通过"剖析实例一抽提要素一建立联系"的程序展开教学.从森林,草原或校园中的实例出发,使学生感受多种生物共同生活在一起是自然界中的普遍现象,理解群落概念的3个要素:?占有一定自然区域(即一定空问和时问内);? 相互作用的不同种群的集合体;?与群落环境共同构成生态系统.同时建立个体,种群,群落与生态系统之间的内在联系.2)群落特征的学习.物种组成,群落外貌及群落结构均属于群落的基本特征,可以指导学生通过"实例观察(或实地调查)一要点分析一整体把握"的思路来学习.标准中提出了2个活动建议辅助教学:一是土壤中动物类群丰富度的研究;二是调查当地自然群落中若干种生物的生态位.教师应指导学生做周密细致的前期准备(制定方案),以保证活动研究的有效性,使学生形成感性认识.在此基础上,教师还要指导学生分析与归纳,明确不同的环境存在着不同的群落,每一群落都具备其特有的基本特征:?物种组成:尽可能列出该群落所含有的各种植物,动物和微生物.?外部形态:描述该群落中植物的生长型f如乔木,灌木,草本和苔藓等)和分层结构.?丰富度:群落中不同物种的个体数量不同,区分其很多,多,尚多,少和稀少.?优势度:找出决定该群落结构和功能的优势种.?群落的结构:包括垂直结构,水平结构和时间格局(季节变化和昼夜变化).?群落的营养结构:群落中的物质流动和能量流动等.3)群落演替的教学.群落的稳定是相对的,南于环境是变化的,群落也不断地发展变化.关于群落的可变性.可以通过探究水族箱(或鱼缸)中群落的变化获得感性认识,即组织学生设计制作水族箱,定期调查水族箱内的植物,动物及微生物的种类和数量,在此基础上进行比较与分析.关于群落的演替,可以通过 "分析阶段一提炼特点一归纳类型"的教学思路展开. 先从具体事例人手,从未有任何生物定居过的裸地如何演变成为具有稳定结构的群落呢?讨论裸地上最先出现的是地衣.随着时问的推移,一些物种会取代原有的一些物种,一个群落类型会被另一个群落类型取代,形成了"地衣阶段一苔藓阶段一草本阶段一灌木阶段一树木阶段"的演替阶段.分析演替具有如下特点:?阶段性;?方向性;?终止在稳定状态,即形成顶极群落;?最终形成了各种适应生存环境的类型. 在此基础上归纳演替的2种类型,并使学生明确顶级群落概念的含义.表4演替的类型与阶段(以森林群落为例) 类型实例(阶段)裸地:地衣阶段一苔藓阶段一草本阶段一灌木阶段一树木阶段湖泊:裸底阶段一沉水植物阶段一浮叶根生植物阶段一挺水植初生演替物阶段一湿生草本植物阶段一灌爪阶段一森林阶段沙丘:滨草一沙拂子茅等一短叶松一黑栎林一山毛榉次生演替弃耕地:马唐草一飞蓬草一紫菀一莽草一短叶松一栎结合实例阐明研究群落的实践意义.如间作,套种等农田人工群落的很多措施,就是利用自然群落层次结构的原理来发展农业生产:又如淡水养鱼中的混合放养,也是根据群落的结构关系,充分利用生态条件获得高产.(E—mial:wangd0ngmei8l09@163.COITIsmxbright@163.COITI)fBZ)些?妇逝业妇花椰菜有助降低患皮肤癌风险美国科学家近日研究发现.花椰菜的一种提取物能帮助人体预防太阳紫外线伤害,从而降低患皮肤癌的风险. 之前在小鼠身上进行的研究发现.花椰菜中含有的异硫氰酸盐(sulforaphane)能帮助减少紫外线照射造成的炎症.在最新研究中,美国约翰?霍普金斯大学的药理学家PaulTalalay和同事让6个志愿者背部接受不同量的紫外线照射,其中有些志愿者使用花椰菜提取物作为防护,另一些则没有.结果发现,如果在紫外线照射前3日每天都使用花椰菜提取物,在照射后, 细胞损伤平均会下降37%.,这表明异硫氰酸盐能够帮助细胞抵御伤害,所 Talalav说以含有异硫氰酸盐成分的药膏能够降低因紫外线照射而患皮肤癌的风险.摘自《科学时报)2007年10月26日\\//一.鲁貌溉升十?一,.,,。

四氢姜黄素及其固体分散体在小鼠体内药动学及相对生物利用度的研究为建立HPLC-MS/MS测定小鼠血浆中四氢姜黄素（THC）浓度的方法，比较四氢姜黄素及其固体分散体在小鼠体内的生物利用度，该实验采用200只SPF 级KM小鼠随机分为2组，在禁食状态下口服给药（THC及其固体分散体，剂量均按THC计：400 mg·kg-1）的方法，通过HPLC-MS/MS系统测定小鼠给予THC及其固体分散体后15，30，45 min，1，1.5，2，3，4，6，24 h血浆中THC 的血药浓度，根据药时曲线采用Phoenix WinNonlin软件计算药动学参数并进行数据分析，计算其相对生物利用度（F）：F=AUCTHC固体分散体/AUCTHC×100%。

经过方法学考证，THC在9.06～972.00 μg·L-1线性良好（R2>0.999），定量下线为2 μg·L-1，最低检测限为0.7 μg·L-1，特异性好，无干扰内源性物质，日内和日间精密度≤13%，回收率高且血浆样品稳定性好，表明该测定方法特异、快速、准确、可靠，可满足四氢姜黄素体内药动学研究需要。

小鼠口服四氢姜黄素及其固体分散体后的药动学参数如下：Tmax分别为60，15 min，AUC0-t分别为44 500.43 mg·L-1·min，57 497.81 mg·L-1·min，AUC0-∞分别为51 226.00 mg·L-1·min，68 031.48 mg·L-1·min，MRT0-∞分别为596.915 6 min，661.747 7 min，CLz/F分别为0.007 809 L·min-1·kg-1，0.005 88 L·min-1·kg-1。

与四氢姜黄素相比，其固体分散体的平均滞留时间（MRT）和消除半衰期（t1/2）都略有延长，达峰时间（tmax）明显提前，且AUC0-24 h，AUC0-∞，Cmax均显著提高，其相对生物利用度是四氢姜黄素的1.34倍。

瓦氏效应名词解释一、定义瓦氏效应（Warburg effect）是指肿瘤细胞即使在有氧的条件下，也会优先进行糖酵解（一种将葡萄糖分解为乳酸的代谢途径），而不是通过正常的有氧呼吸（三羧酸循环和氧化磷酸化）来产生能量的现象。

二、发现者及背景1. 由德国生物化学家奥托·海因里希·瓦尔堡（Otto Heinrich Warburg）发现。

2. 瓦尔堡通过一系列实验观察到肿瘤细胞独特的代谢特征，他发现肿瘤细胞摄取葡萄糖的量远远高于正常细胞，并且大部分葡萄糖被转化为乳酸排出细胞外，这种代谢转变与正常细胞的代谢模式有显著差异。

三、具体代谢过程及特点1. 糖酵解增强在正常细胞中，有氧条件下主要通过线粒体进行有氧呼吸，糖酵解相对较弱。

而肿瘤细胞则大量摄取葡萄糖，并且将其主要导向糖酵解途径。

例如，肿瘤细胞中葡萄糖转运蛋白（如GLUT1等）的表达水平往往上调，使得葡萄糖能够大量进入细胞。

糖酵解途径中的关键酶，如己糖激酶等，在肿瘤细胞中的活性也增强。

己糖激酶可以催化葡萄糖磷酸化，这是糖酵解的起始步骤，肿瘤细胞中己糖激酶的高活性有助于糖酵解的快速进行。

2. 乳酸产生增加在糖酵解过程中，肿瘤细胞将葡萄糖转化为丙酮酸，然后在乳酸脱氢酶（LDH）的作用下，丙酮酸被还原为乳酸。

肿瘤细胞中乳酸脱氢酶的活性通常较高，这使得大量的丙酮酸被转化为乳酸并排出细胞外。

乳酸的产生不仅是糖酵解的一个结果，而且还对肿瘤微环境产生影响。

高浓度的乳酸可以改变肿瘤微环境的pH值，使其偏酸性，这种酸性环境有利于肿瘤细胞的生长、侵袭和转移，同时也会影响免疫细胞的功能，抑制机体的抗肿瘤免疫反应。

3. 有氧呼吸受抑制尽管肿瘤细胞处于有氧环境，但线粒体的有氧呼吸功能受到抑制。

肿瘤细胞的线粒体结构和功能可能存在异常，例如线粒体膜电位可能发生改变，线粒体呼吸链复合物的活性可能降低等。

这种有氧呼吸受抑制而糖酵解增强的代谢模式使得肿瘤细胞能够快速产生能量（虽然糖酵解产生的ATP量相对有氧呼吸较少，但速度较快），同时也为肿瘤细胞的生长和增殖提供了必要的生物合成原料。

卤化1.Dalton反应应用NBS在含水二甲基亚砜中和烯烃的反应，可以得到较高收率、高度立体选择性的对向加成产物β-溴醇（反式加成）2.Hunsdriecker 反应（脱羧卤置换反应）羧酸银盐和溴或典反应，脱出二氧化碳，生产比原反应物少一个C原子的卤代烃。

3.Williamson反应（烃化）醇在碱（钠，氢氧化钠、氢氧化钾等）存在下与卤代烃反应生成醚的反应。

烃化4.F-C 碳酰化羧酸及羧酸衍生物在质子酸或Lewis酸的催化下，对芳烃进行亲电取代生成芳酮的反应。

酰化1.Gattermann反应羟基或烷氧基取代的芳烃在ZnCl2,AlCl3等Lewis酸的催化下与氰化氢和氯化氢反应，生成亚胺盐酸盐，在经水解生成相应的芳醛的反应。

2.Vilsmeier-Haack反应3.Reimer-tiemann反应4.Claisen和Dieckmann反应缩合1.Claisen-Schmidt反应2.Prins反应3.安息香缩合4.Blanc反应（氯甲基化）5.Mannich反应（氨甲基化）反应机理6.β-羟烷基化反应7.Michael反应8.Wittg反应9.羧基α活性亚甲基反应10.α，β-环氧化烷基化反应（Darens反应）11.D-A反应重排12.13.Pinacol重排14.B-B-Z重排15.Favorskii重排16.Beckmann重排17.Hofmann重排18.Stevens重排19.Sommelet-hauser重排20.Claisen重排还原21.Clemansen还原22.黄明龙反应23.氨基保护剂还有BocTHANKS !!!致力为企业和个人提供合同协议，策划案计划书，学习课件等等打造全网一站式需求欢迎您的下载，资料仅供参考。

ICH领域专业术语表（质量、安全性）序号英文中文1"relevant" viruses and "model" viruses“相关”病毒和“模型”病毒225-fold AUC radio25倍的AUC比值3 a single 2 generation study单项包括两代（生殖毒性）的研究4abbreviated or abridged application简略申请5abnormal karyology异常核形6abortions流产7absorbed moisture吸附水8absorption吸收9acceptable daily intake可接受的日摄入量10acceptable test加速试验11acceptance criteia认可标准12accuracy准确性13accuracy准确度14acelerated/stress stability studies加速/强力破坏稳定性研究15acentric fragment无着丝点片段16acetylation 乙酰化作用17achiral assay非手性测定18achlorhydric eldderly老年性胃酸缺乏症19acridine orange吖啶橙20action limits内控限值21active components/compound/moiety活性成分22active ingredient活性组分23active metabolite活性代谢产物24adaption to specific culture conditions特定培养条件的适应25additional test 附加实验26additions添加剂27adduct加合物28adequate exposure充分暴露29adjuvant 佐剂30ADME吸收、分布、代谢、排泄31administration period给药期32adventitious agents外源性因子33adventitious contaminants外来污染物34adventitious viral or mycoplasma contamination外源性病毒或支原体污染35adventitious viruses外源病毒36advers effect不良反应37adverse reaction不良反应38aerobic microorganisms需氧微生物39affinity亲和力40affinity chromatography亲和层析41affinity column亲和柱42against humanised proteins serum antibodies抗人源蛋白血清抗体　43agar and broth琼脂和肉汤44aggregates 聚合体45aggregation聚集46aginal smear阴道涂片　47air ighting reflex空中翻正反射48alkylating electrophilic center烷化亲电子中心49allele基因突变产生的遗传因子50allergenic/allergic extracts过敏原抽提物51allergic reactions过敏性反应（变应性反应）52altenative validated test有效替代试验53altered conjugated forms改变的结合物形式54altered growth 生长改变55ambient condition自然条件56amino acid composition氨基酸组成57amino acid sequence氨基酸顺序58amino acids氨基酸59amino sugars氨基糖60amino-terminal amino acids氨基端氨基酸61ammonia production Rates产氨率62ammoniun sulphide staining of the uterus子宫硫化胺染色　63analogue类似物（同系物）64analogue series of substances同系物65analyte 被测物66analytical method 分析方法67analytical procedure分析方法68anaphase分裂后期69aneuploidy非整倍体70aneuploidy inducer非整倍体诱导剂71animal cell lines动物细胞系72animal tissues or organs动物组织或器官73antennary profile 触角形状74antibiotic resistance genes抗生素耐药基因75antibiotics抗生素76antibody抗体77antibody production tests抗体产生试验78antigenic specificity抗原特异性79antisera抗血清80apoptosis凋亡81applicant申报者82art and ethical standards技术和伦理标准83ascites腹水84assay含量测定85assay procedure定量方法86assessment of genotoxicity遗传毒性评价87attainment of full sexual function达到性成熟　88AUC曲线下面积89auditory startle relex惊愕反射（听觉惊跳反射）90autoimmune自身免疫91autoradiographic assessment放射自显影评价92autoradiography放射自显影93avian鸟类94avidity亲和性95background 背景96bacteria细菌97bacterial mutagenicity test细菌致变突试验98bacterial reverse mutation test细菌回复突变试验99bacterial strains菌株100bacterial test organisms微生物试验菌101base pairs碱基对102base set of strains基本菌株103base substitution碱基置换104batches批次105batch-to-batch逐批106between-assay variation试验间变异107binary fission双数分裂108binding assays结合试验109bioanalytical method生物学分析方法110bioavaiability生物利用度111bioburden生长量/生物负荷112biochemical methods生化方法113bioequivalency生物等效性114biohazard enformation生物有害信息115biological activity生物活性116biological products生物制品117biological relevance生物学意义118bioreactor生物反应器119biotechnological products生物技术产品120biotechnological/biological products生物技术/生物制品121biotechnology-derived pharmaceuticals生物技术药物122biphasic curve双相曲线123birth出生124blood plasma factors血浆因子125body burden机体负担126body fluids体液127bone marrow cell骨髓细胞128bouin's fixation包氏液固定129bovine牛130bovine spongiform encephalopathy(BSE)疯牛病131bracketing括号法132breakage of chromatid染色单体断裂133breakage of chromosome染色体断裂134breeding conditions饲养条件135bridging character桥梁作用136by-products副产物137C(time)一定剂量、某一时间的浓度138calibrate标化139canine犬140cap liner瓶帽内垫141capillary electrophoresis毛细管电泳142carbohydrate碳水化合物143carboxy-terminal amino acids羧基端氨基酸144carcinogen致癌物质145carcinogenesis致癌性146carcinogenic hazard致癌性危害147carcinogenicity bioassay致癌性生物检测148carcinogenicity potential of chemical化合物的潜在致癌性149carcinoginicity(oncogenicity)致癌（致瘤）150cardiovascular心血管151carrier载体/担体152case-by-case个例153catalysts催化剂154cell bank 细胞库155cell bank system细胞库系统156cell banking procedures细胞建库过程157cell banking system细胞库系统158cell culture-derived impurities来源于细胞培养基的杂质159cell cultures 细胞培养物160cell cultures 细胞培养161cell expansion细胞扩增162cell fusion细胞融合163cell line细胞系164cell lines 细胞系165cell membrane lipid细胞膜脂质层166cell metabolites细胞代谢物167cell pooling细胞混合168cell proliferation细胞增植169cell replication system细胞复制系统170cell substrate-derived impurities 来源于细胞基质的杂质171cell substrates细胞基质172cell suspension细胞悬液173cell viability细胞活力174cell-derived biological products细胞来源的生物制品175cell-mediated immunity细胞介导的免疫176cellular blood components血细胞成分177cellular therapy细胞治疗178cemadsorbing viruses红细胞吸附病毒179central nervous systems中枢神经系统180cerbral spinal fluid脑脊液181characterization and testing of cell banks细胞库鉴定及检测182charcoal活性炭183charge电荷184chemical actionmertric system化学光化线强度系统185chemical nature化学性质186chemical reactivity 化学反应性187chemical syntheses化学合成188chemically inert化学惰性189chewable tablets咀嚼片190childbeering potential生育可能性191chinese hamster V79 cell中国仓鼠V79细胞192chiral impurities手性杂质193CHL cell中国仓鼠肺细胞194CHO cell中国仓鼠卵巢细胞195chromatide染色单体196chromatograms色谱图197chromatographic behavior色谱行为198chromatographic procedures色谱方法199chromatography columns色谱分离柱200chromosomal aberration染色体畸变201chromosomal damage染色体损伤202chromosomal integrity染色体完整性203chronic toxicity testing 慢性毒性试验204circular dichroism圆二色性205classfical biotransformation studies经典的生物转化试验206clastogen染色体断裂剂207clastogenic致染色体断裂的208clearance studies清除研究209cleavage of the balanopreputial gland 龟头包皮腺裂开210climatic zones气候带211clinical indication临床适应证212clinical research临床研究213clinical trial application 临床试验申请214clisure闭塞物215cloning 克隆216cloning efficiency克隆形成率217closure of hard palate硬腭闭合218C max峰浓度219coat growth毛发生长220code number编号221coding sequence编码序列222coefficient of variance变异系数223collaborative studies协作实验研究224colony isolation菌落分离225colony sizing集落大小226colony-stimulating factors集落刺激因子227combination product复方制剂228comparative trial对比试验229complement binding补体结合230completely novel compound全新化合物231components成分232compound bearing stuctural alerts结构可疑化合物233concentration threshold阈浓度234conception受孕235concomitant toxicokinetics相伴毒代动力学236confidence interval置信区间237confidence limits可信限238confirmatory studies确认研究239conformance to specifcations符合规范240conformation构型241conjugated product连接产物242conjugation连接243consistency一致性244container容器245container/closure容器/闭塞物246container/closure integrity testing 容器/密封完整性试验247contaminants污染物248contaminated cell substrate污染的细胞基质249content uniformity含量均匀度250continuous treatment 连续接触251control methodology控制方法学252controlled released product控释制剂253conventional live virus vaccines传统的活病毒疫苗254conventional vaccines传统疫苗255cool white fluorescent冷白荧光灯256corpora lutea黄体257corpora lutea count黄体数258correction factor校正因子259correlation coefficient相关系数260covalent or noncovalent共价或非共价261creams霜剂262cross-contamination交叉污染263cross-linking agent交联剂264cross-reactivity交叉反应265cryopreservation冷冻保存266cryoprotectants防冻剂267crystals晶体268culture components 培养基成分269culture condiction培养条件270culture confluency培养克隆率271culture confluenty培养融合272culture media/medium培养基273culture medium培养基274cyanogen bromide溴化氰275cytogenetic细胞遗传学的276cytogenetic change细胞遗传学改变277cytogenetic evaluation细胞遗传学评价278cytokines细胞因子279cytopathic细胞病的280cytoplasmic A-and R-type particles细胞浆a型和r型颗粒281cytotoxicity细胞毒282dark control暗度控制283dead offspring at birth 出生时死亡的子代284deamidation去氨基285deaminated去酰胺化的286deamination脱氨基287decision flow chart/tree判断图288definable and measurable biological activity明确和可测定的生物学活性289degradant降解产物290degradation降解291degradation pathway降解途径292degradation product降解产物293degradation profile降解概况294degree of aggregation 凝集度295degree of scatter离散程度296delay of parturition分娩延迟297delayed-release延迟释放298deleterious有害的299deletion缺失300delivery systems给药体系301derivatives衍生物302description 性状303descriptive statistics描述性统计304detection limit检测限度305detection of bacterial mutagen细菌诱变剂检测306detection of clastogen染色体断裂剂检测307determination of metabolites测定代谢产物308development of the offspring 子代发育309developmental toxicity发育毒性310dilivery systems释放系统311dilution ratio释放倍数312dimers二聚体313diminution of the background lawn背景减少314diode array二极管阵列315diploid cells二倍体细胞316direct genetic damage 直接遗传损伤317dissociation解离318dissolution testing溶出试验319dissolution time溶出时间320distribution分布321DNA adduct DNA加合物322DNA damage DNA损伤323DNA repair DNA修复324DNA strand breaks DNA链断裂325dosage form剂型326dose dependence剂量依赖关系327dose escalation剂量递增328dose level剂量水平329dose -liming toxicity剂量限制性毒性330dose-ranging studies剂量范围研究331dose-related剂量相关　332dose-relatived cytotoxicity剂量相关性细胞毒性333dose-relatived genotoxic activity剂量相关性遗传毒性334dose-relatived mutagenicity剂量相关性诱变性335dose-response curve剂量－反应曲线336dosing route给药途径337downstream purification下游纯化338drug product制剂339drug product components制剂组方340drug substances原料药341duration周期342duration of pregnancy妊娠周期343eaning断奶344earlier physical malformation早期身体畸形345early embryonic development早期胚胎发育346early embryonic development to implantation着床早期的胚胎发育347ectromelia virus脱脚病病毒348elastomeric closures橡皮塞349electro ejaculation电射精350electron microscopy(EM)电镜351electrophoresis电泳352electrophoretic pattern电泳图谱353elimination消除354elution profile洗脱方案355embryofetal deaths胚胎和胎仔死亡356embryo-fetal development 胚胎－胎仔发育357embryo-fetal toxicity胚胎－胎仔毒性358embryonated eggs鸡胚359embryonic death胚胎死亡360embryonic development胚胎发育361embryonic period胚胎期362embryos胚胎　363embryotoxicity胚胎毒性364enantiomer对映体365enantiomer对映异构体366enantiomeric镜像异构体367enantioselective对映体选择性368encephalomyocarditis virus(EMC)脑心肌炎病毒369end of pregnancy怀孕终止370endocytic 内吞噬（胞饮）371endocytic activity内吞噬活性372endogenous agents内源性因子373endogenous components内源性物质374endogenous gene内源性基因375endogenous proteins内源性蛋白376endogenous retrovirus内源性逆转录病毒377endonuclease核酸内切酶378endonuclease release form lysosomes溶酶体释放核酸内切酶379endotoxins内毒素380end-point终点381end-product sterility test-ing最终产品的无菌试验382enhancers增强子383enveloped RNA viruses包膜RNA病毒384environmental factors环境因素385enzymatic reaction rates酶反应速率386enzyme酶387epididymal sperm maturation附睾精子成熟性388epitope表位389epitope抗原决定部位390Epstein-Barr virus (EBV)EB病毒391equine马392error prone repair易错性修复393erythropoietins促红细胞生成素394escalation递增395escherichia coli starn大肠杆菌菌株396esscherichia coli 大肠杆菌397ethnic origin种族起源398eukaryotic cell真核细胞399evaluation of test result试验结果评价400ex vivo体外401exaggerated pharmacological response超常增强的药理作用402excipient赋形剂403excipient specifications赋形剂规范404excretion排泄(消除)405expiration date/dating失效日期406exposure assessment 接触剂量评价407exposure level暴露程度408exposure period光照时间409exposure period接触期410expression constract表达构建体411expression system表达系统412expression vector表达载体413extended-release延时释放414extent of the virus test病毒测试的程度415external metabolising system体外代谢系统416extinction coefficient消光系数417extrachromosomal染色体外418extraneous contaminants外源性污染物419extrapolation 外推法420F1-animals子一代动物421false negative result假阴性结果422false positive result假阳性结果423fecundity多产424feed-back反馈425fermentation发酵426fermentation products发酵产品427fertilisation受精428fertility生育力429fertility studies生育力研究430fetal abnormalities胎仔异常431fetal and neonatal parameters胎仔和仔鼠的生长发育参数432fetal development and growth胎仔发育和生长433fetal period 胎仔期434fetotoxicity胎仔毒性435fill volume装量436filter aids 过滤介质437final manufacturing最终生产438finished product成品439first pass testing 一期试验440flanking region侧翼区441fluorescence in situ hybridisation (FISH)原位荧光分子杂文442foetuses胎仔443forced degradation testing强制降解试验444foreign matter异质性物质445formal labeling正式标签446formal stability studies正式的稳定性研究447formulation 处方/配方448formulation 制剂449fragmentation片段化450frameshift mutation移码突变451frameshift point mutation移码点突变452free-standing独立453freeze-dried product冻干产品454fresh dissection technique新鲜切片技术455friability脆碎度456functional deficits功能试验457functional test功能性指标458funetional indices融合蛋白459fungi真菌460fusion partners融合伴侣461fusion protein融合蛋白462fusion proteins配子463gametes动物性别464gel filtration 凝胶过滤465gender of animals性别专一性药物466gender-specific drug基因剔除467gene amplification基因扩增468gene knockout基因治疗469gene mutation基因突变470gene therapy基因疗法471generation of the cell substrate细胞基质的产生472genetic遗传473genetic change 遗传学改变474genetic damage遗传学损伤475genetic endpoint遗传终点476genetic manipulation基因操作477genetic toxicity遗传毒性478genomic dinucleotide repeats基因组双核苷酸重复数479genomic DNA基因组DNA480genomic polymorphism pattern基因组形态类型481genotoxic activity遗传毒性作用482genotoxic carcinogen遗传毒性致癌剂483genotoxic effect 遗传毒性效应484genotoxic hazard遗传毒性危害485genotoxic potential潜在遗传毒性486genotoxic rodent carcinogen啮齿类动物遗传毒性致癌剂487genotoxicity 遗传毒性488genotoxicity evaluation遗传毒性评价489genotoxicity test遗传毒性试验490genotoxicity test battery遗传毒性试验组合491genotypic 基因型492germ cell mutagen生殖细胞诱变剂493germ line mutation生殖系统突变494GLP临床前研究质量管理规范495glucose consumption rates耗糖率496glycoforms糖化形式497glycosylation糖基化498goegrapgical origin 地理起源499gross chromosomal damage 染色体大损伤500gross evaluation of placenta 胎盘的大体评价501growth factors生长因子502growth hormones 生长激素503guanidine胍504haematoxylin staining苏木素染色505half-life半衰期506hamster antibody production(HAP) test仓鼠抗体产生实验507Hantaan virus汉坦病毒508hardness硬度509heavy metals重金属510hematopoietic cells造血细胞511heparins肝素512heptachlor七氯化合物513herbal products草药514heritable遗传515heritable defect遗传缺陷516heritable disease遗传性疾病517heritable effect 遗传效应518herpes virus 疱疹病毒519heterogeneities异质性520heterohybrid cell lines异种杂交细胞系521high concentration高浓度522high-resolution chromatography高分辨色谱523histologic appearance of reproductive organ生殖器官的组织学表现524histopathological chang组织病理学改变525homogeneity均一性526homologous proteins同系蛋白527homologous series同系528host cell 宿主细胞529host cell banks宿主细胞库530host cell DNA宿主细胞DNA531host cell proteins宿主细胞蛋白质532hot-stage microscopy热价显微镜533human carcinogen人类致癌剂534human cell lines人细胞系535human diploid fibroblasts人二倍体成纤维细胞536human lymphoblastoid TK6 cell 人成淋巴TK6细胞537human mutagen人类致突变剂538human polio virus人脊髓灰质炎病毒539human subjects人体540human tropism人向性541humidity湿度542humidity-protecting containers防湿容器543humoral immunity 体液免疫544hybridization techniques杂交技术545hybridoma cell杂交瘤细胞546hybridomas杂交瘤547hydrolysates水解物548hydrolytic enzymes水解酶549hydrophobicity疏水性550hygroscopic吸湿性551identification/identity鉴别552immature erythrocyte未成熟红细胞553immediate and latent effect速发和迟发效应554immediate container/closure直接接触的容器/密闭物555immediate pack内包装556immediate release立即释放557immortalization激活558immune spleen cells免疫脾细胞559immunoassay免疫检测560immunochemical methods免疫化学方法561immunochemical properties免疫化学性质562immunoelectrophoresis免疫电泳563immunogenicity免疫原性564immunological interations免疫相互作用565immunopathological effects免疫病理反应566immunoreactivity免疫反应性567immunotoxicity免疫毒性568implantation着床569implantation sites着床部位570impurity profile杂质概况571in vitro体外572in vitro and in vivo inoculation tests体内和体外接种试验573in vitro assay体外检测574in vitro cell age体外细胞传代期575in vitro lifespan体外生命周期576in vitro test体外试验577in vitro tests体外试验578in vitro/in vivo correlation体内体外相关性579in vivo体内580in vivo assays体内检测581in vivo test体内试验582inactivated vaccine 灭活疫苗583incidence of polyploid cell 多倍体细胞发生率584incisor eruption门齿萌出585independent test独立试验586indicator cell指示细胞587indicator organisms指示菌588individual fetal body weight单个胎仔体重589indoor indirect daylight室内间接日光590induced and spontaneous models of disease诱发或自发的疾病模型591inducer of micronuclei微核诱导剂592inducers 诱导剂593inedntification test鉴别试验594infectious agents感染性因子595influenza virus流感病毒596inhalation吸入597inhalation dosage forms 吸入剂型598inhibitor of DNA metabolism DNA代谢抑制剂599in-house内部的600in-house criterea内控标准601in-house primary reference material内部一级参比物质602in-house reference materials内部参比物质603in-house working reference material内部工作参比物质604initial filing原始文件605initial submission最初申报606initial text最初文本607inoculation接种608inorganic impurities无机杂质609inorganic mineral无机矿物质610inorganic salts无机盐611in-process acceptance criteia生产过程认可标准612in-process controls生产过程中控制613in-process testing生产过程中检测614insect昆虫615insulins胰岛素616intact animals完整动物（整体动物）617intake摄入618intended effect预期效果619intended storage period 预期的贮藏期620intentional degradation人为降解621interactions相互作用622interferon干扰素623interleukins白细胞介素624intermediate中间体625intermediate precision中间精密度626intermediates半成品627internal control内对照628international reference standards国际参比标准品629interphase muclei分裂间期细胞核630intra-and inter-individual个体与个体间631intra-assay precision间隙含量精密度632intracytoplasmic细胞浆内633introduction of virus病毒介入634inverted or horizontal position倒立或水平位置635ion-exchange离子交换636ionic content离子含量637isoelectric focusing/isoelectrofocusing等电聚焦638isoenzyme analysis同工酶分析639isoform pattern异构体类型640isolated organs离体器官641isomerized 异构化的642Jp/Ph.Eur./Usp.日本药局方/欧洲药典/美国药典643juvenile animal studies未成年动物研究644K virus K病毒645karyology胞核学646Kinetic profile动力学特点647Kinetics 动力学648laboratory scale实验室规模649lactate production rates乳糖产生速率650Lactating授乳、哺乳651lactic dehydrogenase virus (LDM)乳酸脱氢酶病毒652Large deletion event大缺失事件653Late embryo loss后期胚胎丢失654leachables沥出物655Level of safety安全水平656Libido性欲657Life threatering危及生命658ligand 配位体/配体659light光照660light resistant packaging避光包装661limit for in vitro cell age 细胞体外传代限度662limit of acceptance可接受的限度663limit of in vitro cell age 体外细胞代次664limit test限度试验665limulus amoebocyte lysate鲎试剂666linear relation ship 线性关系667linearity线性668Lipophilic compound亲脂性化合物669liquid nitrogen 液氮670liquid oral dosage forms 液体口服制剂671Litter size每窝胎仔数目672Live and dead conceptuese活胎和死胎673Live offspring at birth出生时存活的子代674live vaccine 活疫苗675living cells活细胞676Local toxicity局部毒性677Lockl tolerance studies 局部耐受性研究678Locu位点679logarithmic scale:对数级680long term test长期试验681Long-term carcinogenicity study长期致癌性试验682long-time and accelerated stability长期和加速稳定性试验683Loss of the tk gene tk 基因丢失684losses of activity活性丧失685lot release 批签发686low molecular weight subsances低分子量物质687lower-observed effect level (LOEL)能观察到反应的最低量688lymphocytic choriomeningitis virus (LCM)淋巴细胞性脉络丛脑膜炎病毒689lyophilised cakes冻干粉饼690lysate of cells 细胞溶解物691Major organ fomeation主要器官形成692Male fertility雄性生育力693Male fertility assessment雄性生育力评价694mammalian哺乳类695Mammalian cell mutation test哺乳动物细胞致突变试验696Mammalian cells哺乳动物细胞697Mammalian species哺乳类动物698manufacturing scale生产规模699marieting pack 上市包装700marker chromosome 标志染色体701marketing approval批准上市702Marketing approval上市许可703mass 重量704mass balance质量平衡705mass spectrometry质谱706master cell bank (MCB)主细胞库707Matemal animal亲代动物708material balance物质平衡709Mating behaviour交配行为710Mating period交配期711Mating ratio交配比例712Matrices基质713matrix基质、矩阵714matrix system矩阵化设计715matrixing每日最大剂量716maximum daily dose平均动力学温度717Maximum tolerated dese(MTD)最大耐受剂量718mean kinetic temperature后生动物细胞培养719Mechanism of genotoxicity遗传毒性机制720Mechanistic activation代谢活化721Mechanistic activation pathway代谢活化途径722Mechanistic activation system代谢活化系统723Mechanistic investigation机制研究724Metabolism代谢725Metabolites profile代谢物的概况726Metaphase中期727Metaphase analysis分裂中期相分析728Metaphase cell分裂中期细胞729metazoan cell culture微生物细胞培养730microbial cells微生物细胞731microbial contamunation 微生物污染732microbial expression system微生物表达系统733microbial limits微生物限度734microbial metabolites微生物代谢物735microbial proteases微生物蛋白酶736microbial vaccine antigens微生物疫苗抗原737microbiological testing 微生物学试验738Micronucleus微核739Micronucleus formation微核形成740Microtitre微滴定741Microtitre method微滴定法742Mimicking模拟743minimum exposure time最低作用时间744minimum of pilot plant试产规模745minute virus of mice小鼠小病毒746mirror image 镜像747mismached S-S linked错连的S-S键748Mitotic index有丝分裂指数749modified-/modifying release修饰释放750modifying factor修正因子751moisture level水分752molar absorptivity克分子吸收753Molecular characterisation分子特性754molecular characteristics分子特性755molecular confirmation分子构型756molecular entities/entity分子实体757molecular size分子大小758Molecular technique分子技术759Monitor监测760Monoclonal antibodies单克隆抗体761monoclonal antibody单克隆抗体762mork run空白对照试验763morphological analysis形态学分析764mouse antibody production (MAP) test小鼠抗体产生试验765mouse cytomegalovirus (MCMV)小鼠巨细胞病毒766mouse encephalomyelitis virus (GDVII)小鼠脑脊髓炎病毒767mouse hepatitis virus (MHV)小鼠肝炎病毒768Mouse lymphoma tk assay小鼠淋巴瘤tk检测769Mouse lymphoma L5178Y cell小鼠淋巴瘤L5178Y细胞770mouse rotavirus (EDIM)小鼠小轮状病毒771MuLV murine leukemia virus鼠白血病病毒772murine hybridoma cell lines鼠杂交瘤细胞系773Mutagen诱变原774Mutagen carcinogen诱变性致癌剂775Mutagen potential of chemical化合物的潜在致突变性776Mutant colony突变体集落777Mutation突变778Mutation induction in transgenes转基因诱导突变779mutations 突变780mycoplasma支原体781myeloma cell line骨髓瘤细胞系782Naked eye肉眼783national or international reference material国家或国际参比物质784national reference standards国家参比标准品785near ultraviolet lamp近紫外灯786Necropsy(macroscopic examination)解剖（大体检查）787Negative control阴性对照788Negative result阴性结果789Neonate adaptation to extrautenrine life新生仔宫外生活的适应性790neural sugars中性糖791new chemical entity新化学体792new dosage form新剂型793new drug products/produce新药制剂794new drug substance新原料药795new molecular entities新分子体796Newbom新生仔797Newcleated有核798no effect level不产生反应的量799Non rodent非啮齿类800Non-clinical非临床801noncovalent/convalent forces非共价/共价键802non-enveloped viruses非包膜病毒803Non-genotoxic carcinogen非遗传毒性致癌剂804Non-genotoxic mechanism非遗传毒性机制805Non-human primate非人灵长类806Non-linear非线性807non-mammalian animal cell lines非哺乳动物细胞系808non-recombinant cell-cul-ture expression systems非重组细胞培养表达系统809non-recombinant products/vaccines非重组制品/疫苗810non-specific model virus非特异模型病毒811Non-toxic compound无毒化合物812Non-toxic-effect dose level无毒性反应剂量水平813no-observed effect level不能观察到反应的量814N-terminal sequencing N端测序815nuclear magnetic resonance 核磁共振816Nucleated bone marrow cell有核骨髓细胞817nucleic acid核酸818Nucleoside analogue核苷酸同系物819nucleotide sequences 核苷酸序列820Number of live and dead implantation宫内活胎和死胎数821Numerical chromosmal aberration染色体数目畸变822Numerical chromosome changes染色体数目改变823Oestrous cycle动情周期824official procedure正式方法825ointments软膏826oligonucleotide低聚核苷酸827Oligonucleotide grugs寡核苷酸药物828oligosaccharide pattern寡糖类型829One,two,three generation studies一、二、三子代研究830opacity浊度831Organ development器官发育832organic impurities有机杂质833origins of replication复制起点834osmolality摩尔渗透压浓度835outdoor daylight室外日光836Ovulation rate排卵率837oxidation氧化838oxygen consumption rates耗氧量839package包装840Paraffine embedding石蜡包埋841parainfluenza virus副流感病毒842parallel control assays 平行对照分析843Parameter参数844Parent compound母体化合物845parent stability Guideline稳定性试验总指导原则846parental cell line母细胞系847Parenteral非肠道848parenterals非肠道制剂849particle size粒度850Particulate material颗粒物851particulate matter微粒852Parturition分娩延迟853parvoviruses细小病毒854passage history of the cell line细胞系的传代史855pathogenic agents致病因子856pathogenicity致病性857patterns of degradation降解方式858Pediatric populations小儿人群859peptide肽860peptide map 肽图861percent recovery回收率862periodic/skip testing定期检验/抽验863Peripheral blood erythrocyte外周血红细胞864permitted daily exposure允许的日接触量865Perpoductive competence生殖能力866phage typing噬菌体分型867pharcodynamic studies药效学研究868Pharmacodinetic药代动力学869Pharmacodynamic effects药效作用870Pharmacodynamics药效学（药效动力学）871pharmacopoeial药典872pharmacopoeial pharmacoppeial specifications药典规范873pharmacopoeial standards药典标准874phenotypic 表型875Phenylene diamine苯二胺876phosphorylation磷酸化作用877photostability testing光稳定性试验878Physical development身体发育879physicochemical changes理化改变880physicochemical methods物理化学方法881physico-chemical properties物理化学特性882Physiological stress生理应激883Pilot studies 前期研究884pilot-plant scale试生产规模/中试规模885Pinna unfolding耳廓张开886piston release force活塞释放力887piston travel force活塞移动力888pivotal stability studies关键的稳定性研究889plaque assays菌斑测定890plasmid质粒891Plasmid质粒892plasmid banks质粒库893plasminogen activators纤溶酶原激活素894Plasminogen activators纤维蛋白溶解酶原激活因子895Ploidy整倍体896pneumonia virus of mice小鼠肺炎病毒897Point mutation点突变898poisson distribution泊松分布899Polychromatic erythrocyte嗜多染红细胞900polyclonal antibody多克隆抗体901Polycyclic hydrocarbon多环芳烃902Polymer聚合物903polymerase chain reaction (PCR)聚合酶链式反应904polymorphic form多晶性型905polymorphs多晶型906polyoma virus多瘤病毒907polypeptides多肽908Polyploid cell多倍体细胞909Polyploidy多倍体910Polyploidy induction多倍体诱导911pooled havest集中回收912Poorly soluble compound难溶化合物913population doubling细胞数倍增/群体倍增914porcine猪915Positive control阳性对照916Positive result阳性结果917Post meiotic stages减数分裂后期918Post-approval批准后919Postcoital time frame交配后日期920Postimplantation deaths着床后死亡921Postnatal deaths出生后死亡922post-translational modifications批准后923post-translationally modified forms翻译后修饰924Postweaning development and growth断奶后发育和生长925potency效价926potent功效927Potential 潜在性928potential adverse consequences潜在的不良后果929potential excipients准赋形剂930Potential immunogenecity潜在免疫原性931potential impurity潜在杂质932potential new drug products准新药制剂933potential new drug substances准新药原料934Potentialtarget organs for toxicity潜在毒性靶器官935potentiometric titrimetry电位滴定936powders粉剂937power outages and human error断电和人为错误938preamble引言939Pre-and post-natal development study围产期的发育研究940Pre-and postweaning survival and growth断奶前后的存活和生长941pre-approval or pre-liscense stage批准前或发证前阶段942Precipitate沉淀物943precision精密度944preclinical and clinical studies临床前和临床研究945Preclinical safety evaluation临床前安全性评价946precursors前体947Predetermined criteria预定标准948Prediction of carcinogenicity致癌性预测949Pregnant怀孕950Pregnant and lactating animals怀孕与哺乳期动物951Preimplantation development着床前发育952Preimplantation stages of the embryo胚胎着床前期953preliminary assessment初步评估954preliminary cell bank初级细胞库955Preliminary studies预试验956Premating交配前957Premating treatment交配前给药958preparation制剂959Pre-screening预筛选960preservative防腐剂961Prevalence of abnormalities异常情况的普遍程度962Preweaning断奶前963Primary active entity主要活性实体964primary cells原代细胞965primary stability data主要稳定性数据966primary stability study/formal study/formal stability study主要稳定性研究/正式研究/正式稳定性研究967primary structure一级结构968primer引物969priming regimen接种方案970Priority selection优先选择971probability概率972process characterisation studies工艺鉴定研究973process controls工艺控制974process optimisation工艺优化975process parameters工艺参数976process validation工艺确证977process-related impurities工艺相关杂质978Pro-drug前体药物979product-related imputies产品相关杂质980progenitor祖细胞981prokaryotic cell原核细胞982Prolongation of parturition产程延长983promoters启动子984proposed commercial process模拟上市985protected samples避光样品。