4-氟-3-甲基-2-噻吩羧酸 | 187962-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 4-氟-3-甲基-2-噻吩羧酸
• 英文名称: α-carboxy-β-methyl-γ-fluorothiophene
• 英文别名: 4-Fluoro-3-methylthiophene-2-carboxylic acid
• CAS: 187962-16-9
• 化学式: C₆H₅FO₂S
• 分子量: 160.169
• InChiKey: KCTKTYADQWAXNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  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

文献信息

• 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.