(Z)-3-Fluoro-4-phenylsulfanyl-but-3-en-2-one | 167965-53-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-3-Fluoro-4-phenylsulfanyl-but-3-en-2-one
• 英文别名: (Z)-3-fluoro-4-phenylsulfanylbut-3-en-2-one
• CAS: 167965-53-9
• 化学式: C₁₀H₉FOS
• 分子量: 196.245
• InChiKey: OOOWTNGGYVSXOF-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium (2-methoxy-2-oxoethyl)sulfanide 、 (Z)-3-Fluoro-4-phenylsulfanyl-but-3-en-2-one 在 盐酸 作用下， 生成 4-氟-3-甲基-2-噻吩羧酸
  参考文献：
  名称：

  Reaction of thioglycolate with α-fluoro-β-(phenylthio)enones (or -enals): Synthesis of substituted α-carboxy-γ-fluorothiophenes

  摘要：

  A new synthetic method to substituted alpha-carboxy-gamma-fluorothiophenes 2F is reported. They were prepared by the reaction between two equivalents of methyl thioglycolate anion and alpha-fluoro-beta-(phenylthio)enones (or -enals) 1F, in DMSO (70 degrees C) in yields ranging from 41% to 85%. We show from the reaction of (Z)-alpha-fluoro-beta-(phenylthio)but-enone 1aF, that cyclisation to fluorothiophene 2aF occurs via the formation of stable enolates of alpha-fluoro-beta-(dithianyl)butanone. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02509-9
• 作为产物：
  描述：

  (E)-4-(phenylthio)but-3-en-2-one 在 base 作用下， 生成 (Z)-3-Fluoro-4-phenylsulfanyl-but-3-en-2-one
  参考文献：
  名称：

  Reaction of thioglycolate with α-fluoro-β-(phenylthio)enones (or -enals): Synthesis of substituted α-carboxy-γ-fluorothiophenes

  摘要：

  A new synthetic method to substituted alpha-carboxy-gamma-fluorothiophenes 2F is reported. They were prepared by the reaction between two equivalents of methyl thioglycolate anion and alpha-fluoro-beta-(phenylthio)enones (or -enals) 1F, in DMSO (70 degrees C) in yields ranging from 41% to 85%. We show from the reaction of (Z)-alpha-fluoro-beta-(phenylthio)but-enone 1aF, that cyclisation to fluorothiophene 2aF occurs via the formation of stable enolates of alpha-fluoro-beta-(dithianyl)butanone. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02509-9

文献信息

• Anodic functionalization of vinyl sulfides. Formal access to gem or vicinal aryl thioether dications
  作者：Didier F Andres、Eliane G Laurent、Bernard S Marquet、Hassiba Benotmane、Abdelkader Bensadat

  DOI：10.1016/0040-4020(95)00009-w

  日期：1995.2

  clearly show that the reactivity of the vinyl sulfide radical cation depends on several factors as structure of substrates and nucleophilic conditions. For example a dimerization occurred from the unsubstituted vinyl sulfide 1a (CH2=CH-SPh) whereas α,β- and/or β,β-difluoro sulfides were obtained from substituted homologues. In order to understand this reactivity the anodic behaviour of 1a and 1b (Ph-CH=CH-SPh)

  许多乙烯基硫醚的阳极氧化已在CH 3 CN-Et 3 N，3HF中进行。结果清楚地表明，乙烯基硫化物自由基阳离子的反应性取决于多种因素，如底物的结构和亲核条件。例如，未取代的乙烯基硫化物1a（CH 2＝ CH-SPh）发生了二聚，而α，β-和/或β，β-二氟硫化物是从取代的同系物获得的。为了理解这种反应性，已经特别在另外两种亲核介质（CH 3 OH / Et 3）中分析了1a和1b（Ph-CH = CH-SPh）的阳极行为。N，3HF和AcOH / AcOK）分别导致起始化合物的甲氧基化和乙酰氧基化。与电氟化结果的比较使我们能够提出一种涉及中间epi离子的机理，该机理可以解释分离产物的形成和比例。
• Reaction of thioglycolate with α-fluoro-β-(phenylthio)enones (or -enals): Synthesis of substituted α-carboxy-γ-fluorothiophenes
  作者：Didier F. Andrès、Eliane G. Laurent、Bernard S. Marquet

  DOI：10.1016/s0040-4039(96)02509-9

  日期：1997.2

  A new synthetic method to substituted alpha-carboxy-gamma-fluorothiophenes 2F is reported. They were prepared by the reaction between two equivalents of methyl thioglycolate anion and alpha-fluoro-beta-(phenylthio)enones (or -enals) 1F, in DMSO (70 degrees C) in yields ranging from 41% to 85%. We show from the reaction of (Z)-alpha-fluoro-beta-(phenylthio)but-enone 1aF, that cyclisation to fluorothiophene 2aF occurs via the formation of stable enolates of alpha-fluoro-beta-(dithianyl)butanone. (C) 1997, Elsevier Science Ltd.