Choline Fenofibrate

酰胺键广泛存在于天然产物和药物分子中，经典的构建方法是羧酸和胺在缩合剂的作用下进行缩合，目前缩合剂的种类也是多种多样如HATU，DCC，T3P，PyBOP，HBTU，DPPA等。 1.Coupling via acid chloride SOCl2 and (COCl)2, the two are most widely employed reagents in process chemistry. A drawback of these methods is that HCl is a byproduct of acid chloride generation, which can lead to incompatibility with acid-sensitive functional groups. Amide Bond Formation with SOCl2:  Amide Bond Formation with POCl3:  Amide Bond Formation with POCl3:   Amidation via Vilsmeier Reagent:  2.Coupling via acid anhydride 2.1 Carboxylic/ Carbonic Acid Anhydrides Amide bond formation via mixed anhydride is one of the oldest approaches. Carbon-based mixed anhydrides can be subdivided into two categories depending on the type of activating reagent. Activation with Acetic Anhydride: PivCl-Mediated Coupling: Ethyl Chloroformate-Mediated Coupling:Amidation via IBCF: Boc2O-Mediated Amide Coupling: EEDQ as the Activating Agent:  2.2 Sulfonate-Based Mixed Anhydrides Sulfonate-based mixed anhydrides derived from either reagent display excellent selectivity in which amines add preferentially to the activated carbonyl instead of the sulfonate ester. Amide Couplings via MsCl Activation: Amide Coupling via TsCl Activation:  2.3 Phosphorus-Based Mixed Anhydrides T3P and EMPA have been applied by process chemistry groups for the synthesis of drug candidates. However, EMPA relatively high toxicity (LD50=7 mg/kg) and the need for its low level purging from drug substances have limited use of this reagent on industrial scale.  T3P as the Activating Agent: Amide Forming  via Ethylmethylphosphinic Anhydride: Amide Coupling via Imidazolide: 3.Coupling via Activated Ester 3.1 Carbodiimides A primary consideration when selecting a carbodiimide is the preferred workup since the method for removal of the urea byproduct can vary widely. 1-hydroxybenzotriazole (HOBt) is by far the most commonly used for carbodiimide-mediated reactions in either stoichiometric or catalytic fashion. DCC-Mediated Coupling: DIC/HOBt-Mediated Amidation: EDC/HOBt-Mediated Amidation: 3.2 Phosphonium Salts BOP was the first reagent of the HOBt-basedonium salts to be introduced for amide bond formation to avoid epimerization and other side reactions that can take place with carbodiimide reagents.  Amide Bond Formation with BOP:  3.3 Guanidinium and Uronium Salts These reagents afford fast amide bond formations and can be very useful for the coupling of sterically hindered amino acids in peptide synthesis. Amide Coupling with HBTU: HATU-Mediated Amide Bond Formation: Amide Bond Formation via TBTU: Amide Bond Formation with TBTU: TOTU as a Coupling Agent: 4.Triazine-Based Coupling Reagents Cyanuric chloride is a highly reactive coupling reagent produced on the industrial scale by the hundreds of thousands of metric tons per year via trimerization of cyanogen chloride. Cyanuric Chloride-Mediated Amide Bond Formation: CDMT-Promoted Amide Formation: DMTMM as Coupling Reagent:  5.Coupling via Boron Species Boric acid clearly stands out as a very desirable reagent since it is inexpensive and displays excellent atom economy. In addition, after reaction completion, the water-soluble reagent can be extracted into an aqueous workup. ABBREVIATIONS (缩写): BOP:(benzotriazol-1-yloxy)tris(dimethylamino)phosphoniumhexafluorophospha -te  CDI: 1,1′-carbonyldiimidazole  CDMT: 2-chloro-4,6-dimethoxy-1,3,5-triazine  DCC: N,N′-dicyclohexylcarbodiimide  DCU: N,N′-dicyclohexylurea  DIC: N,N′-diisopropylcarbodiimide   DMTMM: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride  ECF: ethyl chloroformate  EDAC: 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide  EDC or EDCI: 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide  EEDQ: 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline  EMPA: ethylmethylphosphinic anhydride  HATU:N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide  HBTU:N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide  HOAt: 1-hydroxy-7-azabenzotriazole  HOBt: N-hydroxybenzotriazole  HONB: N-hydroxy-5-norbornene-endo-2,3-dicarboxylic acid imide  HOOBt: 3,4-dihydro-3-hydroxy-4-oxo-(1,2,3)-benzotriazine  IBCF: isobutyl chloroformate  MsCl: methanesulfonyl chloride  PPA: n-propanephosphonic acid anhydride  Piv: pivaloyl py: pyridine  PyBOP:(benzotriazol-1-yloxy)tris(pyrrolidine)phosphonium hexafluorophosphate  PyBrop: bromotripyrrolidinophosphonium hexafluorophosphate  T3P: n-propanephosphonic acid anhydride  TBTU:N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate Noxide  TMP: 2,2,6,6-tetramethylpiperidine  TOTU:O-[(cyano(ethoxycarbonyl)methyleneamino]N,N,N′,N′-tetramethyluronium tetrafluoroborate  TPTU: 2-(2-oxo-1(2H)-pyridyl-1,1,3,3-tetramethyluronium tetrafluoroborate  TsCl: p-toluenesulfonyl chloride  内容来源：Org. Process Res. Dev. 2016, 20, 140−177

反应前装置的英语描述 A 3 L three-necked round bottom flask equipped with mechanical stirrer (or magnetic stirrer), addition funnel and thermometer (or Dean-Stock; drying tube) All flasks used in the reaction were heated under vacuum for 30 minutes and purged with N2 for 10 minutes. (无水反应装置) 加料过程的英语描述 添加试剂  To a mixture (suspension/solution/slurry) of compound 12 (487 mg, 1 mmol) and o-phenylenediamine (648 mg, 6 mmol) in CH2Cl2 (15 mL) cooled to 0 ℃ was added DCC (226 mg, 1.1 mmol). Anhydrous lithium iodide (1.38 g, 10.3 mmol) was added in five portions (dropwise/in one portion/in portions/portionwise) to a stirred solution of compound 12 (10.93 g, 51.5 mmol) in CH2Cl2 (120 mL). A 3 L three-necked round bottom flask equipped with mechanical stirrer, addition funnel and thermometer (or Dean-Stock; drying tube) were charged with A (10 mL, 1mol), B (2 g, 1 mol) and C (50 mL). 分批加入 in portions/portionwise 一次性加入 in one portion 滴加 dropwise A round-bottom flask was charged with compound 33 (1.75 g, 5.27 mmol), LiCl (1.17g, 26.3 mmol), DMSO (100 mL) and H2O (378 μL). 反应控温  A solution of compound 1 (10 g , 1 mole) in EtOAc (20 mL) was added dropwise (via addition funnel or syringe) to the above mixture at 10 ℃ (while maintaining gentle reflux; while keeping internal temperature between 10 ℃ – 30 ℃) under N2. 催化量的试剂  Et3N (20 mL, 142 mmol) and a catalytic amount of DMAP were added to a solution of compound 1 (4.549 g, 46.4 mmol) in CH2CH2 (120 mL) at 0 ℃. 气体保护   To a stirred –78 ℃ solution of trimethylsilylacetylene (4.44 g, 45.2 mmol) in THF (10 mL) under Argon was added dropwise n-butyllithium (1.6 M in hexane, 28.25 mL). 通入气体   An ozone-enriched stream of oxygen was bubbled through a cold (-78 ℃) solution of compound 9a (128 mg, 0.409 mmol) in CH2Cl2 (5 mL) until it turned light blue. The solution was purged with argon at -78 ℃ for 10 min to remove excess O2. 通过双针头管加料   This mixture was added to a solution of compound 2 (3.00 g, 12.8 mmol) in THF (48 mL) via cannula over a period of 30 min. A solution of compound 29 (100 mg, 0.19 mmol, 1.0 equiv) in dry DMSO (0.5 mL) was cannulated under Ar to a vigorously stirred mixture of powdered potassium superoxide (62 mg, 0.87 mmol, 4.5 equiv) and 18-crown-6-ether (23 mg, 0.087 mol, 0.45 equiv) in dry DMSO (0.5 mL). 通过注射器加料   To a stirred solution of compound 15a (8.61 g, 21.2 mmol) was added a solution of p-toluenesulfonic acid (6.0 mg) in CH2Cl2 (4.0 ml) via syringe over 5 min. 常温/回流搅拌   The reaction mixture (solution or suspension) was stirred at 5 ℃ for 2 hrs and then kept at room temperature (or ambient temperature) for another 2 hrs (or overnight) The reaction mixture (solution or suspension) was refluxed (or heated to reflux) for 2 hrs (or overnight) The reaction mixture (solution or suspension) was heated at 60 ℃ for 2 hrs (or overnight) The reaction mixture (solution or suspension) was allowed to reflux (or heat to reflux) for 2 hrs (or overnight) 反应检测   After 1 h, TLC analysis (CH2Cl2/hexanes 3:1) showed the complete consumption of compound 15. The reaction was complete (incomplete or messy) detected by TLC (Petroleum ether/EtOAc 4:1), LC-MS, HPLC or NMR. 保温过程   The mixture was left standing overnight. The mixture was allowed to stand at room temperature for 1 day. The mixture was allowed to stand in a freezer at -15 ℃. 用甲苯带水   Compound 4A (1.97 g, 6.63 mmol) was coevaporated with toluene five times to remove H2O. The residue was subjected to toluene azeotrope to give the corresponding acid chloride as a brown oil. 氢化反应   A mixture of compound 1 (190 g, 0.88 mol) and Raney Ni (20 g) in ethanol (1500 mL) and ethyl acetate (500 mL) was stirred under 1 atm of H2 at room temperature for 1 hour. 分水器   A mixture of TsOH.H2O (56.91 g, 0.30 mol) and toluene (400 mL) was heated to reflux to remove water by Dean-Stark trap. 反应放热   The reaction was exothermic. 微波反应   The sealed vial was irradiated in the microwave on a Biotage Smith Synthesizer at 150 ℃ for 10 min. After the mixture was heated under microwave irradiation at 130 ℃ for 15 min, Boc2O (33 mg, 157 μmol) and triethylamine (16 μl, 117 μmol) were added. 抽真空   The mixture was degassed for 10 min and refilled with N2. 吸收装置   The device for absorbing the evolved hydrogen bromide was attached to the reaction flask. [care!! The reaction evolves HBr and is best connected to a HBr gas trap (bubbler containing 1 M NaOH solution)]. 避光反应   To the solution which is protected from light was added dropwise Br2 (3.45 g, 22 mmol) in CH2Cl2 (10 mL) over 5 min and the mixture was stirred for 1 h. A mixture of compound 8 (213 mg, 0.186 mmol) and compound 9 (220 mg, 0.279 mmol) was refluxed for 20 h under dark in a nitrogen atmosphere.后处理过程中常用的表述 过滤   The mixture was filtered through a Celite pad, and the filtrate was concentrated to give crude product. 淬灭   The reaction mixture was quenched by the addition of saturated aqueous NH4Cl. An aqueous solution of A (0.5 M, 10 mL) was added dropwise into the reaction mixture once the reaction mixture (solution or suspension) was warmed (or cooled) to -5 ℃ or room temperature (ambient temperature). The hot (or cold) reaction mixture (solution or suspension) was poured into water (ice water) or poured onto ice. The reaction mixture (solution or suspension) was concentrated (distilled) under reduced pressure (in vacuum) or evaporated to remove MeOH (THF; DMF etc.) or excess SOCl2 (reagent). The residue (or the residual) was diluted with solvent and poured into water (ice water) or poured onto ice. 分液   After quenching the reaction, the reaction mixture was poured into separatory funnel and separated. 磨碎   The residue was triturated with ether and filtered to afford a white solid. 在xxxx 中两相分开，隔开   The residue was partitioned between EtOAc (100 mL) and 1 N aq. HCl (50 mL). The organic layer was washed with H2O, dried (MgSO4) and evaporated to dryness. EtOAc (100 mL) and 1 N aq. HCl (50 mL) were added to the residue, and the layers were separated. 静止固化   The crude product was purified by prep. HPLC to give compound 4 as a colorless thick oil which was solidified on standing. 冻干机冻干   The white solid (105249x43A) was re-crystallized from water, dried by hyophilization to give WP-100418 (105249x43B, 45.0 g, 39.2%) as a white solid. 纯化   过柱： The crude product was chromatographed on silica gel (acetone/dichloromethane 10:90→10:80→10:70) to give compound 8 (0.282 g, 51%) as a white solid. The crude product was purified by column chromatography on silica gel eluted with acetone/dichloromethane (10:90~10:80~10:70) to give compound 8 (0.282 g, 51%) as a white solid. 制备的 HPLC 纯化 be purified by preparative HPLC to afford/give/yield 制备的 TLC 纯化 be purified by preparative TLC to afford/give/yield 重结晶 recrystallized from 调节pH   The pH was adjusted to around 9 by progressively adding solid NaHCO3. The mixture was adjusted to pH 9 with solid NaHCO3. 酸化: be acidified to 碱化: be basified to 中和: be neutralized 萃取   The combined aqueous layers were extracted with EtOAc (100 mL×4) (or 4 times) to remove neutral impurities. The aqueous phase was acidified (or basified) with aqueous HCl (or NaHCO3) and extracted with CH2Cl2 (100 mL×5). The combined organic layers were dried over MgSO4 and concentrated. 浓缩   The mixture was evaporated to afford the crude product. The mixture was concentrated to afford the crude product. The solvent was removed to afford the crude product. 真空干燥   The precipitate was filtered and dried in vacuo (in/under vacuum; under reduced pressure). acetal     醛缩醇acetyl-     乙酰acid       酸-al       醛alcohol 醇-aldehyde 醛alkali- 碱allyl 烯丙基 [propenyl(丙烯基)]alkoxy- 烷氧基-amide 酰胺amino- 氨基的-amidine 脒-amine 胺-ane 烷anhydride 酐anilino- 苯胺基aquo- 含水的-ase 酶-ate 含氧酸的盐、酯-atriyne 三炔azo- 偶氮 benzene 苯bi- 在盐类前表示酸式盐bis- 双-borane 硼烷bromo- 溴butyl 丁基 -carbinol 甲醇carbonyl 羰基-carboxylic acid 羧酸centi- 10-2 chloro- 氯代cis- 顺式condensed 缩合的、冷凝的cyclo- 环 deca- 十deci 10-1 -dine 啶dodeca- 十二 -ene 烯epi- 表epoxy- 环氧-ester 酯-ether 醚ethoxy- 乙氧基ethyl 乙基 fluoro- 氟代form 仿 -glycol 二醇 hemi- 半hendeca- 十一hepta- 七heptadeca- 十七hexa- 六hexadeca- 十六-hydrin 醇hydro- 氢或水hydroxyl 羟基hypo- 低级的，次hyper- 高级的，高 -ic 酸的，高价金属-ide 无氧酸的盐，酰替 胺，酐-il 偶酰-imine 亚胺iodine 碘iodo- 碘代iso- 异，等，同-ite 亚酸盐 keto- 酮ketone 酮 -lactone 内酯 mega- 106 meta- 间，偏 methoxy- 甲氧基 methyl 甲基  micro- 10-6milli- 10-3 mono- ( mon-) 一，单 nano- 10-9 nitro- 硝基nitroso- 亚硝基nona- 九nonadeca- 十九 octa- 八octadeca- 十八-oic 酸的-ol 醇-one 酮ortho- 邻，正，原-ous 亚酸的，低价金属oxa- 氧杂-oxide 氧化合物-oxime 肟oxo- 酮oxy- 氧化-oyl 酰 para- 对位，仲penta- 五pentadeca- 十五per- 高，过petro- 石油phenol 苯酚phenyl 苯基pico- 10-12 poly- 聚，多 quadri- 四quinque- 五 semi- 半septi- 七sesqui 一个半sulfa- 磺胺sym- 对称syn- 顺式，同，共 ter- 三tetra- 四tetradeca- 十四tetrakis- 四个thio- 硫代trans- 反式，超，跨thio- 硫代tri- 三trideca- 十三tris- 三个 undeca- 十一uni- 单，一unsym- 不对称的，偏位 -yl 基-ylene 撑(二价基，价在不同原子上)-yne 炔 有机合成中常见术语 1,4-addition 1，4-加成   Absolute configuration 绝对构型   Abstraction 夺取[反应]   Achiral 非手性[的]   Aci form 酸式   Acid-base catalyxed reaction 酸性溶剂   Acid-base catalyzed reaction 酸碱催化反应   Activating group 活化基团   Acyl cation 酰[基]正离子   Acyl rearrangement 酰基重排   Acylation 酰化   Acyloin condensation 偶姻缩合   Acylolysis,acyl cleavage 酰基裂解   acyloxyation 酰氧基化   Addition-elimination mechanism 加成消除机理   Additive dimerization 加成二聚   Alcoholysis 醇解   Aldol condensation 羟醛缩合   Alkylation 烷基化   Alkylidene group 亚烷基   Alkylolysis,alkyl cleavage 烷基裂解   Allyl group 烯丙基   Allylic halogenation 烯丙型卤化   Allylic hydroperoxylation 烯丙型氢过氧化   Allylic migration 烯丙型迁移   Allylic migration 烯丙型重排   Allylic 烯丙型[的]   Alternant hydrocarbon 交替烃   Ambident 两可[的]   Amination 氨基化   Aminomercuration 氨汞化   Aminomethylation 氨甲基化   Amphi position 远位  Angular methyl group 角甲基   Anionic cleavage 负离子裂解   Anionic cycloaddition 负离子环加成   Anionotropic rearrangement 负离子转移重排   Anionotropy 负离子转移   Annulation,annelation 增环反应   Anomer 端基[差向]异构体   Anomeric effect 端基异构效应   Antarafacial reaction 异面反应   Anti conformation 反式构象   Anti periplanar conformation 反叠构象   Antiaromaticity 反芳香性   Anti-Markovnikov addition 反马氏加成   Anti-Zaitsev orientation 反札依采夫定向   Apofacial reaction 反面反应   Arenirm ion 芳[基]正离子   Aromatic nucleophilic substitu-tion 芳香亲核取代   Aromatic sexter 芳香六隅   Aromaticity 芳香性   Aromatization 芳构化   Aryl action 芳正离子   Aryl group 芳基   Arylation 芳基化   Asymmetric atom 不对称原子   Asymmetric carbon 不对称碳   Atropismer 阻转异构体   Autoxidation 自氧化   Auxochrome 助色团   Axial bond 直[立]键   B strain 后张力   Backside attack 背面进攻   Banana bond 香蕉键   Basic solvent 碱性溶剂   Benzilic rearrangement 二苯乙醇酸重排   Benzyl group 苄基   Benzylic cation 苄[基]正离子   Benzylic 苄型[的]   Benzyne 苯炔   Bimllecular base-catalyzed al- kyl-oxygen cleavage 双分子碱催化烷氧断裂   Bimolecular base-catalyzed acyl-oxygen cleavage 双分子碱催化酰氧断裂   Bimolecular electrophilic substi-tution 双分子亲电取代   Bimolecular elimination through the conjugate base 双分子共轭碱消除   Bimolecular elimination with for-mation of a carbonyl group 双分子羰基形成消除   Bimolecular elimination 双分子消除   Bimolecular nucleophilic sub-stitution 双分子亲核取代   Bimolecular nucleophilic substi-tution(with allylic rearrange-ment) 双分子亲核取代（含烯丙型重排）   Bimolecular reduction 双分子还原   Bisamination 双氨基化   Bisecting conformation 等分构象   Boat conformation 船型构象   Borderline mechanism 边理机理   Bredt rule 布雷特规则   Briddgehead displacement 桥头取代   Bridged-ring system 桥环体系   C- alkylation C-烷基化   Cahn-Ingold-Prelon sequence 顺序规则   Carbalkoxylation 烷氧羰基化   Carbanion 碳负离子   Carbene 卡宾   Carbenoid 卡宾体   Carbine 碳炔   Carboamidation 氨羰基化   Carbocation 碳正离子   carbonylation 羧基化   Carboxylation 羧基化   Catalytic dehydrogenation 催化脱氢   Catalytic hydrogenation 催化氢化   Cationotropic rearrangement 正离子转移重排   Chair conformation 椅型构象   Chelation 螯环化   Chiletropic reaction 螯键反应   Chiral center 手性中心   Chiral molecule 手性分子   Chiral 手性[的]   Chirality 手性   Chlorocarbonylation 氯羰基化   Chlorosulfenation 氯亚磺酰化   Chlorosulfonation 氯磺酰化   Cholromethylation 氯甲基化   Chromophore 生色团   Cine substitution 移位取代   Cisoid conformation 顺向构象   Cis-trans isomerism 顺反异构   Common ring 普通环   Condensation 缩合   Configuration 构型   Conformation 构象   Conformational effect 构象效应   Conformational inversion 构象反转   Conformational transmission 构象传递   Conformational 构象分析   Conformer 构象异构体   Conjugate addition 共轭加成   Conjugate base 共轭碱   Conjugate base 共轭酸   Conjugated-system 共轭体系   Conjugation 共轭   Conrotatory 顺旋   Coordinate-covalent bond 配位共价键   Counrer[gegen]ion 反荷离子   Coupling reaction 偶联反应   Cram’s rube 克拉姆规则   Cross aldol condensation 交叉羟醛缩合   Cross conjugation 交叉共轭   Cross-coupling reaction 交叉偶联反应   Cyanoethylation 氰乙基化   Cyanomethylation 氰甲基化   Cyclization 环化   Cycloaddition 环加成   Deactivating group 钝化基团   Deamination 脱氨基   Decarbonylation 脱羰   Decarboxamidation 脱酰胺   Decarboxylation 脱羧   Decarboxylative nitration 脱羧卤化   Decarboxylative nitration 脱羧硝化   Decyanation 脱氰基   Decyanoethylation 脱氰乙基   Dehalogenation 脱卤   Dehydrohalogenation 脱卤化氢   Delocalezed bond 离域键   Demethylation 脱甲基化   Deoxygenation 脱氧   Deselenization 脱硒   Desulfonation 脱磺酸基   Desulfurization 脱硫   Dextro isomer 右旋异构体   Diamagnetic ring cruuent 抗磁环电流   Diastereomer 非对映[异构]体   Diastereotopic 非对映异位[的]   Diaxial addition 双直键加成   Diazo transfer 重氮基转移   Diazonium coupling 重氮偶联   Diazotization 重氮化   Dielectric constant 介电常数   Diels-Alder reaction 第尔斯-尔德反应   Diene synthesis 双烯合成   Dienophile 亲双烯体   Dimerization 二聚   Dipolar addition 偶极加成   Disroatatory 对旋   Dissolving metal reduction 溶解金属还原   D-L system of nomenclature D-L命名体系   Double bond migration 双键移位   E isomer E异构体   Eclipsed conformation 重叠构象   Eclipsing effect 重叠效应   Eclipsing strain 重叠张力   Electrical effect 电场效应   Electrochemical oxidation 电化学氧化   Electrochemical reduction 电化学还原   Electrocyclic rearrangement 电环[化]重排   Electrofuge 离电体   Electron donof-acceptor complex,EDAcomplex 电子给[体]受体络合物   Electron transfer 电子转移   Electron-donating group 给电子基团   Electron-Withdrawing group 吸电子基团   Electrophile 亲电体   Electrophilic addition 亲电加成   Electrophilic aromatic substitu-tion 亲电芳香取代   Electrophilic rearrangement 亲电重排   Electrophilic substitution 亲电取代   elimination -消除   -elimination -消除   Elimination-addition 消除-加成   Enantiomer 对映[异构]体   Enantiotopic 对映异位[腯   Endo addition 内型加成   Endo isomer 内型异构体   Ene synthesis 单烯合成   Enolization 烯醇化   Envelope conformation 信封[型]构象   Epimer 差向异构体   Epoxidation 环氧化   Equatorial bond 平[伏]键   Erythro configuration 赤型构型   Erythro isomer 赤型异构体   Esterification 酯化   Ethanolysis 乙醇解   Ethylation 乙基化   Exhaustive methylation 彻底甲基化   Exo addition 外型加成   Exo isomer 外型异构体   F strain 前张力   Field effect 场效应   Fischer projection 费歇尔投影式   Flash pyrolysis 闪热裂   Fluxional structure 循变结构   Forbidden transition 禁阻跃迁   Formylation 甲酰化   Fragmentation 碎裂   Gauche conformation, skew con-formation 邻位交叉构象   Guest 客体   Half-chair conformation 半椅型构象   Haloalkylation 卤烷基化   Haloform reaction 卤仿反应   Hammond postulate 哈蒙德假说   Helical molecule 螺旋型分子   Heterogeneous hydrogenation 多相氢化   Heterolysis 异裂   Heterolytic michanism 异裂机理   Heterotopic 异位[的]   Hofmann’s rule 霍夫曼规则   Homoaromaticity 同芳香性   Homochiral 纯手性[的]   Homogeneous hydrogenation 均相氢化   Homolog 同系物   Homologization 同系化   Homolysis 均裂   Homosigmatropic rearrangement 同迁移重排  Homotopic 等位[的]   Host 主体   Huckel’rule 休克尔规则   Hydroacylation 加氢酰化   Hydroboration 硼氢化   Hydrocarboxylation 氢羧基化   Hydroformylation 加氢甲酰基化   Hydrogenolysis 氢解   Hydrometallation 氢金属化   Hydroxyalkylation 羟烷基化   Hydroxylation 羟基化   Hydroxymethylation 羟甲基化   Hyperconjugation 超共轭   I strain 内张力   Imine-enamine atutomerism 亚胺-烯胺互变异构   Inductive effect 诱导效应   Initiation 引发   Insertion 插入   Intermediate 中间体   Internal abstraction 内夺取[反应]   Internal nucleophilic substiru-tion 分子内亲核取代   Internal return 内返   Inverse isotope effect 逆同位素效应   Inversion 反转   Ion pair 离子对   Ipso position 本位   Isoinversion 等反转   Isomerism 异构[现象]   Isoracemization 等消旋   Isovalent hyperconjugation 等价超共轭   Keto-enol tautomerism 酮-烯醇互变异构   -ketol rearrangement -酮醇重排   Ketyl radical 羰自由基   Kinetic acidity 动力学酸度   Kinetic control 动力学控制   Laevo isomer 左旋异构体   Large angle strain 大角张力   Large ring 大环   Leaving group 离去基团   Leois structure 路易斯结构   Linear free energy 线性自由能   Lithiation 锂化   Magnetically anisotropic group 磁各向异性基团   Markovnikov’s rube 马尔科夫尼科规则   Masked carbanion 掩蔽碳负离子   Mechanism 机理   Medium rimg 中环   Mercuration 汞化   Meso compound 内消旋化合物   Mesomeric effect 中介效应   Meta directing group 间位定位基   Meta position 间位   Michael addition 迈克尔加成   Microscopic reversibility 微观可逆性   Migration 迁移   Migratory aptitude 迁移倾向   Mirror symmetry 镜面对称   Mitallation 金属化   Mobius system 默比乌斯体系   Molecular orbiral method 分子轨道法   N-alkylation N-烷基化   Neighboring group effect 邻基效应   Neighboring group participation 邻基基参与   Neighboring proup assistance,anchimeric assistance 邻助作用   Neoman projection 纽曼投影式   Nitration 硝化   Nitrene 氮宾   Nitrosation 亚硝化   No-bond resonance 无键共振   Non-alternant hydrocarbon 非交替烷   Non-bonded interaction 非键相互作用   Nonclassical carbocation 非经典碳正离子   Nucleofuge 离核体   Nucleophile-assisted unimolecu-lar electrophilic substitution 亲核体协助单分子亲电取代   Nucleophilic reaction 亲核反应   Nucleophilicity 亲核体   Nucleophilicity 亲核性   O- alkylation O-烷基化   Octahedral compound 八面体化合物   Optical activity 光学活性   Orinentation 取向   Ortho effect 邻位效应   Ortho position 邻位   Ortho-para directing group 邻对位定位基   Oxidative decarboxylation 氧化脱羧   Oxo process 羰基合成   Oxonolysis 臭氧解   Oxyamination 羟氨基化   Oxymercuration 羟汞化   Para position 对位   Paramagnetic ring current 顺磁环电流   Partial bond fixation 键[的]部分固定化   Partial rate factor 分速度系数   Pauling electronegativity scale 鲍林电负性标度   Peri position 近位   Pericyclic reaction 周环反应  Phantom atom 虚拟原子  Phase-transfer catalysis 相转移催化   Phenol-keto tautomerism 酚-酮互变异构   Phenyl group 苯基   Photochemical rearrangement 光化学重排   Photoisomerization 光异构化   photooxidation 光氧化   Photosensitization 光敏化   Pinacol rearrangement 频哪醇重排   Pitzer strain 皮策张力   Plane of symmetry 对称面   Polarizability 可极化性   Prelog’rule 普雷洛格规则   Primary isotope effect 一级同位素效应   Prochirality 前手性   Pro-R group 前R基团   Pro-S proup 前S基团   Prototropic rearrangement 质了转移重排   Prototropy 质子转移   Pseudoasymmetric carbon 假不对称碳  Pseudorotation 假旋转   Puckered ring 折叠环   Push-pull effect 推拉效应   Pyrolytic elimination 热解消除   Quasi recemate 准外消旋体   Racemic compound 外消旋化合物   Racemic mixture 外消旋混合物   Racemic solid solution 外消旋固体溶液   Racemization 外消旋化   Radical anion 自由基负离子   Radical cation 自由基正离子   Radical ion 自由基离子   Re face Re面   Reactive intermediate 活泼中间体   Rearrangement 重排   Reductive acylation 还原酰化   Reductive alkylation 还原烷基化   Reductive dimerization 还原二聚  Regioselectivity 区域选择性   Regiospecificity 区域专一性   Resonance effect 共振效应   Resonance 共振   Restricted rotation 阻碍旋转   Retention of configuration 构型保持  Retro Diels-Alder reaction 逆第尔斯-阿尔德反应   Retrograde aldol condensation 逆羟醛缩合   Retropinacol rearrangement 逆频哪醇重排   Ring clsure 环合   Ring contraction 环缩小[反应]   Ring expansion,ring enlargement 扩环[反应]   Ring-chain tautomerism 环-链互变异构   Rotamer 旋转异构体   R-S syytem of nomenclature R-S命名体系   Saponification 皂化   Seco alkylation 断裂烷基化   Secondary isotope effect 二级同位数效应   Selenylation 硒化   Semipinacol rearrangement 半频哪醇重排   Si face Si面   Sigmatropic rearrangement -迁移重排   Silylation 硅烷[基]化   Single electron transfer 单电子转移   Skew boat conformation 扭船型构象   Small-angle strain 小角张力   Smally ring 小环   Solvated electron 溶剂化电子   Solvent effect 溶剂效应   Spiro compound 螺环化合物   Spiroannulation 螺增环   Staggered conformation 对位交叉构象   Stereocelectivity 立体选择性   Stereochemical orientation 立体[化学]取向   Stereochemistry 立体化学   Stereoisomerism 立体异构[现象]   Stereospecificty 立体专一性   Steric effect 空间效应   Steric hindrance 位阻   Substitution 取代   Substrate 底物   Sulfenylation 亚磺酰化   Sulfonation 磺化   Sulfonylation 磺酰化   sulfurization 硫化   Symmetry factor 对称因素   Symmetry forbidden-reaction 对称禁阻反应   Synclinal conformation 反错构象   Synclinal conformation 顺错构象   Synfacial reaction 同面反应   Synperiplanar conformation 顺叠构象   tautomerism 互变异构   Tautomerization 互变异构化   Tetrahedral configuration 四面体构型   Therm odynamic acidity 热力学酸度   Thermodynamic control 热力学控制   Threo configuration 苏型构型   Threo isomer 苏型异构体   Torsion angle 扭转角   Torsional effect 扭转效应   Transacetalation 缩醛交换   Transamination 氨基交换   Transannular insertion 跨环插入   Transannular interaction 跨环相互作用   Transannular rearrangement 跨环重排   Transannular strain 跨环张力   Transesterification 酯交换   Transfer hydrogenation 转移氢化   Transoid conformation 反向构象   Trigonal carbon 三角型碳   Trigonal hybridization 三角杂化   Trimefization 三聚   Twist conformation 扭型构象   Umbrella effect 伞效应   Unimolecular acid-catalyzed acyl-oxygen cleavage 单分子酸催化酰氧断裂   Unimolecular acid-catalyzed alkyl-oxygen cleavage 单分子酸催化烷氧断裂   Unimolecular electrophilic sub-stitution 单分子亲电取代   Unimolecular elimination through the conjugate base 单分子共轭碱消除   Unimolecular elimination 单分子消除   Unimolecular nucleophilic 单分子亲核取代   Valence bond method 价键法   Valence tautomerism 价互变异构   Vinylog 插烯物   Walden inversion 瓦尔登反转   Z isomer Z异构体   Zaitsev rule 札依采夫规则   α-effect α-效应   π-allyl complex mechanism π烯丙型络合机理