位置：成果数据库 > 期刊 > 期刊详情页
三氟亚乙基取代的M-苯甲酰基氮杂环丙烷的合成
  • ISSN号：0253-2786
  • 期刊名称：《有机化学》
  • 分类：O626[理学—有机化学;理学—化学] TQ453.2[化学工程—农药化工]
  • 作者机构：[1]东华大学化学化工与生物工程学院,上海201620, [2]中国科学院上海有机化学研究所有机氟化学重点实验室,上海200032
  • 相关基金：国家自然科学基金（Nos.20832008,20672020）资助项目.
作者： 吴伟[1], 黄焰根[1], 卿凤翎[1,2]
关键词： 三氟亚乙基, 氮杂环丙烷, 开环反应, trifluoroethylidene, aziridine, ring opening reaction
中文摘要：

发展了一种制备三氟亚乙基取代的N-苯甲酰基氮杂环丙烷的新颖方法．三氟甲基取代的炔丙胺化合物1在盐酸作用下脱去叔丁基亚磺酰基得到三氟甲基炔丙胺盐酸盐2，当用NaOH作碱对2进行苯甲酰化反应时意外地以中等产率获得了N-苯甲酰基．2．三氟亚乙基氮杂环丙烷类化合物3a-3c．在类似条件下也可以从1出发采用“一锅法”制得氮杂环丙烷3d和3e．化合物3b可以在酸催化下发生开环反应得到化合物6b．化合物3和6的结构经IR，1HNMR，19FNMR，MS，HRMS和元素分析进行确证．

英文摘要：

A novel method for preparation of trifluoroethylidene substituted N-benzoyl aziridine compounds was developed. Trifluoromethylated propargyl sulfinamides （1） were converted to trifluoromethylated propergylamine hydrochloride 2 via acidic cleavage of the tert-butanesulfinyl groups. N-Benzoyl-2-trifluoroethylideneaziridines 3a-3c were surprisingly obtained in moderate yields by the ben- zoylation reaction of 2 when using NaOH as base. Aziridines 3d-3e can also be obtained in a one pot process starting from propargyl sulfinamides 1.3b can undergo ring opening reaction under acidic condition to afford compound 6b. The structures of products 3 and 6 were confirmed by IR, 1H NMR, 19F NMR, MS spectra and elemental analyses.

同期刊论文项目
含氟生物活性物质的分子设计与合成
期刊论文 122
含氟天然产物类似物的合成
期刊论文 16 会议论文 2
同项目期刊论文
Selective Nucleophilic Fluoroalkylations Facilitated by Removable Activation Groups. (Account)
Copper-catalyzed oxidative trifluoromethythiolation of aryl boronic acids with TMSCF3 and elemental
Stereoselective Reformatskii-Claisen rearrangement: synthesis of 2 ';,3 ';-dideoxy-6 ';,6 ';-difluor
Methyl carboniumion migration during the reaction of 4-chloro-5-methoxyl-3(2H)-pyridazinone with tri
Synthesis of Fluorinated Chiral Amines Using N-tert-Butylsulfinyl Imines.
Highly Diastereoselective Synthesis of α-Difluoromethyl Amines from N-tert-Butylsulfinyl Ketim
Nucleophilic Difluoromethylation of N,N-Acetals with TMSCF2SO2Ph Reagent Promoted by Trifluoroacetic
Synthesis of Photochromic 1,2-Dithienylethene Derivative with a 2,2,5,5-Tetrafluoro-2,5-dihydrofuran
Cu(II)-mediated methylthilation of aryl C-H bonds with DMSO
A Practical Approach to Synthesize the C(9)-C(24) Fragment of (+)-Discodermolide
Nucleophilic (phenylsulfonyl) difluoromethylation of alkyl halides using PhSO2CF2SiMe3: preparation
Synthesis of gem-difluoromethylenated analogues of anamarine
Recent advances in the synthesis of fluorinated nucleosides
Coupling of sterically hindered aldehyde with fluorinated synthons: Stereoselective synthesis of flu
Palladium catalyzed direct alpha-arylation of alpha,alpha-difluoroketones with aryl bromides
Difluoromethylation of O-, S-, N-, C-Nucleophiles Using Difluorotri(n-butyl)ammonium Chloride as a N
From Difluoromethyl 2-Pyridyl Sulfone to Difluorinated Sulfonates: A Unique Protocol for Nucleophili
Highly Enantioselective Zinc(BINOL)-Catalyzed Alkynylation of ?-Ketoimine Esters
Highly Diastereoselective Synthesis of Quaternary ?-Trifluoromethyl ?-Amino Acids by Addition of Ben
Studies on the synthesis of nicotinamide nucleoside and nucleotide analogues and their inhibitions t
A novel membrane permeantcADPRantagonist modified in the pyrophosphate bridge
Synthesis of ?-monofluorinated goniothalamin analogous via regio- and stereoselective ring-opening h
Synthesis and antiviral activities of isonucleosides and their monophosphates
Concise syntheses of trifluoromethylated cyclic and acyclic analogues of cADPR
Trifluoromethylated cyclic-ADP-ribose mimic: synthesis of 8-trifluoromethyl-N1-[(5’’-O-p
Direct Pd-Catalyzed Benzylation of Highly Electron-Deficient Perfluoroarenes
Total synthesis of gem-difluoromethylenated analogs of Pironetin
Copper-mediated aerobic oxidative trifluoromethylation of terminal alkynes with Me3SiCF3
Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids
Palladium-catalyzed cross-coupling of ethyl -fluoro- -bromoacetate with arylboronic acids: facile sy
Benzoyl peroxide (BPO)-promoted oxidative trifluoromethylation of tertiary amines with trimenthyl(tr
Pd(OAc)2 Catalyzed Olefination of Highly Electron-deficient Perfluoroarenes
Diastereoselective Synthesis of Propargylic Fluorides and Its Application in Preparation of Monofluo
Highly Diastereoselective Synthesis of Quaternary ?-Trifluoromethyl ?-Amino Acids from Chiral Imines
Highly diastereoselective synthesis of ?-trifluoromethylated ?-propargylamines by acetylide addition
Polymer Electrolyte Membranes Based on Poly(norbornene)s with Pendant Difluoroalkyl Sulfonic Acids.
Direct Pdlladium-Catalyzed Intermolecular Allylation of Highly Electron-Deficient Polyfluoroarenes.
Synthesis of 2 ';,3 ';-dideoxy-6 ';-fluorocarbocyclic nucleosides via Reformatskii-Claisen rearrange
Pd-Catalyzed Highly Regio- and Stereocontrolled Direct Alkenylation of Electron-deficient Polyfluoro
Chlorodifluoromethyl Aryl Ketones and Sulfones as Difluorocarbene Reagents. The Substituent Effect.
Pd-Catalyzed Direct Cross-Coupling of Electron-Deficient Polyfluoroarenes with Heteroaromatic Tosyla
The prodrugs of L­guanosine analogs:design, synthesis and anti­HIV activity
Chloride Ion-Catalyzed Generation of Difluorocarbene for Efficient Preparation of gem-Difluorinated
Synthesis of gem-Difluorinated Cyclopropanes and Cyclopropenes：Trifluoromethyltrimethylsilane as a D
Derivatization of beta-dicarbonyl compound with 2,4-dinitrophenylhydrazine to enhance mass spectrome
Highly Stereoselective Synthesis of Monofluoroalkenes from α-Fluorosulfoximines and Nitrones
Bronsted Acid Mediated (sp3)Carbon-Fluorine Bond Activation: Inter- and Intramolecular Arylation of
CuBr-catalyzed oxidative difluoromethylation of tertiary amines with difluoroenol silyl ethers
Highly Diastereoselective Zinc/SnCl2-Mediated gem-Difluoroallylation of Chiral Hydrazones: Synthesis
Synthesis of trifluoroethylidene substituted N-benzoyl aziridines
Nucleophilic, Radical, and Electrophilic (Phenylsulfonyl)difluoromethylations
Synthesis of Fluorinated β-Ketosulfones and gem-Disulfones by Nucleophilic Fluoroalkylations of
Difluoromethylenated polyhydroxylated pyrrolidines: facile synthesis, crystal structure and biologic
Copper-mediated oxidative cross-coupling reaction of terminal alkynes with ?-silyldifluoromethylphos
Synthesis of gem-difluoromethylenated analogues of boronolide
Palladium-Catalyzed 2,2,2-Trifluoroethylation of Organoboronic Acids and Esters
Efficient Synthesis and Ring-Opening Reactions of Monofluorinated Epoxides Derived from α-Fluo
C-F Bond Cleavage by Intramolecular SN2 Reaction of Alkyl Fluorides with O- and N-Nucleophiles
Copper and Phosphine Ligand-Free Palladium-Catalyzed Direct Allylation of Electron-Deficient Polyflu
Asymmetric synthesis of ?-aryl-?-trifluoromethyl-?-aminoarones via Mannich-type reactions of ketone
Copper-Mediated Fluoroalkylation Reactions with [(Phenylsulfonyl) difluoromethyl] trimethylsilane: S
Recent advances of trifluoromethylations
Copper Catalyzed Cross-Coupling of Iodobenzoates with Bromozincdifluorophosphonate
Synthesis and biological evaluation of nicotinamide adenine dinucleotides analogues as inhibitors of
Selective Fluoroalkylation of Organic Compounds by Tackling the ‘Negative Fluorine Effect
Palladium-Catalyzed Allylation of 2,2,2-Trifluoroethyl Phenyl Sulfone: A Potential 2,2,2-Trifluoroet
Copper-Mediated Trifluoromethylation of α-Diazo Esters with TMSCF3: The Important Role of Wate
Synthesis of fluoroalkylated allylic amine derivatives via palladium-catalyzed Overman rearrangement
Copper-Catalyzed Di- and Trifluoromethylation of α,β-Unsaturated Carboxylic Acids: A Prot
Regio- and Diastereoselective Nickel-Catalyzed Allylation of Aromatic Aldehydes with alpha-Halo-beta
Pd-Catalyzed Direct Arylation of Polyfluoroarenes on Water under Mild Conditions Using PPh3 Ligand
Nucleophilic Fluoroalkylation of a,β-Unsaturated Carbonyls with α-Fluorinated Sulfones: I
Nucleophilic Difluoromethylation of C=N Bonds in Heterocycles with Difluoromethyl Silane Reagents
Palladium-catalyzed direct ?-arylation of ?-fluoroketones: A straightforward route to ?-fluoro--aryl
Difluoro(phenylchalcogen)methylation of aldehydes, ketones, and imines with S-, Se-, and Te-containi
Pd-Catalyzed Dehydrogenative Cross-Coupling of Polyfluoroarenes with Heteroatom-Substituted Enones
Synthesis and biological evaluation of SGLT2 inhibitors: gem-difluoromethylenated Dapagliflozin anal
Design and synthetic investigation toward gem-difluoromethylenated forstriecin analogue
Copper-Catalyzed Difluoromethylation of, -Unsaturated Carboxylic Acids: An Efficient Allylic Difluor
Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkenes Using Nucleophilic CF3SiMe3: Eff
Sequential Electrophilic Trifluoromethanesulfanylation-Cyclization of Tryptamine Derivatives: Synthe
From Olefination to Alkylation: In-Situ Halogenation of Julia-Kocienski Intermediates Leading to For
Enantioselective Construction of Fluorinated Tertiary Stereogenic Carbon Centers in Cyclopropanes: A
An Improved Copper-Mediated Oxidative Trifluoromethylation of Terminal Alkynes
Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes
3-DeazanaplanocinA（3-DNPA）的新合成方法
L-异核苷掺入的二核苷酸的合成与抗HIV活性研究
含有二氟亚甲基的Fostriecin类似物的设计和合成研究
化学修饰的干扰RNA及其缀合物
新型含短氟碳链侧基的氧杂环丁烷单体的合成与表征
作用于酪氨酸激酶的抗肿瘤小分子抑制剂γ-氟代Goniothalamin类似物的设计与合成
以2,2,5,5-四氟-2,5-二氢呋喃桥连的1,2-二噻吩乙烯类光致变色分子的合成
Difluoromethylation of O-, S-, N-, C-Nucleophiles Using Difluoromethyltri（n-butyl）ammonium Chloride as a New Difluorocarbene Source
Synthesis and conformational analysis of d-2'-deoxy-2',2'-difluoro-4'-dihydro-4'-thionucleosides.
Synthesis and biological evaluation of potent glycosidase inhibitors: 4-deoxy-4,4-difluoroisofagomin
Synthesis of 2,3,4-Trideoxy-4,4-difluoro-D-ribo-hexopyranose Adenosines
Stereoselective Reformatskii-Claisen rearrangement: synthesis of 2 ',3 '-dideoxy-6 ',6 '-difluoro-2
Highly Diastereoselective Zn/SnCl2-Mediated gem-Difluoroallylation of Chiral Hydrazones
Ruthenium-catalyzed 1,3-dipolar cycloaddition of trifluoromethylated propargylic alcohols with azide
Synthesis and utilization of trifluoromethylated amino alcohol ligands for the enantio selective Ref
Asymmetric synthesis of trifluoromethylated propargylamines via 1,2-additions of trifluoromethylacet
Synthesis of gem-difluorinated nucleoside analogues of the liposidomycins and evaluation as MraY inh
Stereoselective construction of 1,1,1-trifluoroisopropyl moiety by asymmetric hydrogenation of 2-(tr
Synthesis of 3 ',3 '-Difluoro-2 '-hydroxymethyl-4 ',5 '-Unsaturated carbocyclic nucleosides
Total synthesis of trifluoromethylated analogs of macrosphelide A
以2,2,5,5-四氟-2,5-二氢呋喃桥连的1,2-二噻吩乙烯类光致变色分子的合成
期刊信息
  • 《有机化学》
  • 中国科技核心期刊
  • 主管单位:
  • 主办单位:中国化学会 中国科学院上海有机化学研究所
  • 主编：陈庆云
  • 地址：上海市枫林路354号
  • 邮编：200032
  • 邮箱：bianji@mail.sioc.ac.cn
  • 电话：021-54925244
  • 国际标准刊号：ISSN：0253-2786
  • 国内统一刊号：ISSN：31-1321/O6
  • 邮发代号:4-285
  • 获奖情况:
  • 中国期刊方阵“双效”期刊
  • 国内外数据库收录:
  • 俄罗斯文摘杂志,美国化学文摘（网络版）,荷兰文摘与引文数据库,美国科学引文索引（扩展库）,日本日本科学技术振兴机构数据库,中国中国科技核心期刊,中国北大核心期刊（2004版）,中国北大核心期刊（2008版）,中国北大核心期刊（2011版）,中国北大核心期刊（2014版）,中国北大核心期刊（2000版）
  • 被引量:14408