Ethyl α-chloro-α-fluoro-α-(phenylthio)acetate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Ethyl α-chloro-α-fluoro-α-(phenylthio)acetate
• 英文别名: Ethyl 2-chloro-2-fluoro-2-phenylsulfanylacetate
• 化学式: C₁₀H₁₀ClFO₂S
• 分子量: 248.706
• InChiKey: BNWMNGUFIQBBPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl phenylsulfanyldichloroacetate 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以52%的产率得到Ethyl α-chloro-α-fluoro-α-(phenylthio)acetate
  参考文献：
  名称：

  Fluorination of α,α-dichlorosulfides: access to gem-difluorothioethers as useful building blocks

  摘要：

  The synthesis of alkylsulfanyidifluoro-acetate and ketones by the Halex reaction is described. The remarkable reactivity of thiodifluoroacetate derivatives opened rapid access for the preparation of useful building blocks such as gem-difluoroketones and amides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01134-1

文献信息

• Electrolytic Partial Fluorination of Organic Compounds. 17. Regiospecific Anodic Fluorination of Sulfides Bearing Electron-Withdrawing Substituents at the Position .alpha. to the Sulfur Atom
  作者：Toshio Fuchigami、Moriyasu Shimojo、Akinori Konno

  DOI：10.1021/jo00116a037

  日期：1995.6

  Regiospecific monofluorination of various sulfides bearing electron-withdrawing substituents, cyano, ester, acyl, amino, and phosphonate groups,at their alpha-positions was successfully carried out by the anodic oxidation of the sulfides in Et(3)N . 3HF/MeCN using an undivided cell. Fluorine was introduced at the position alpha to the sulfur atom selectively. Fluorination of alpha-(phenylthio)-substituted cyclic carbonyl compounds was also successful. Furthermore, anodic alpha,alpha-difluorination of ethyl alpha-(phenylthio)acetate was also successfully carried out although a large amount of electricity was required.
• Fluorination of α,α-dichlorosulfides: access to gem-difluorothioethers as useful building blocks
  作者：Sonia Gouault、Cécile Guérin、Laurent Lemoucheux、Thierry Lequeux、Jean-Claude Pommelet

  DOI：10.1016/s0040-4039(03)01134-1

  日期：2003.6

  The synthesis of alkylsulfanyidifluoro-acetate and ketones by the Halex reaction is described. The remarkable reactivity of thiodifluoroacetate derivatives opened rapid access for the preparation of useful building blocks such as gem-difluoroketones and amides. (C) 2003 Elsevier Science Ltd. All rights reserved.