Ethyl α-fluoro-α-(p-tolylthio)acetate | 130612-81-6

• 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-fluoro-α-(p-tolylthio)acetate
• 英文别名: Acetic acid, fluoro[(4-methylphenyl)thio]-, ethyl ester；ethyl 2-fluoro-2-(4-methylphenyl)sulfanylacetate
• CAS: 130612-81-6
• 化学式: C₁₁H₁₃FO₂S
• 分子量: 228.287
• InChiKey: CTZYFXGJDXDDTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  4-甲基-(苯基硫代)乙酸乙酯 以 乙腈 为溶剂， 以78%的产率得到Ethyl α-fluoro-α-(p-tolylthio)acetate
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 17. Regiospecific Anodic Fluorination of Sulfides Bearing Electron-Withdrawing Substituents at the Position .alpha. to the Sulfur Atom

  摘要：

  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.

  DOI：

  10.1021/jo00116a037

文献信息

• Electrolytic partial fluorination of organic compounds. 1. Regioselective anodic monofluorination of organosulfur compounds
  作者：Toshio Fuchigami、Moriyasu Shimojo、Akinori Konno、Kiyono Nakagawa

  DOI：10.1021/jo00312a006

  日期：1990.12
• FUCHIGAMI, TOSHIO;SHIMOJO, MORIYASU;KONNO, AKINORI;NAKAGAWA, KIYONO, J. ORG. CHEM., 55,(1990) N5, C. 6074-6075
  作者：FUCHIGAMI, TOSHIO、SHIMOJO, MORIYASU、KONNO, AKINORI、NAKAGAWA, KIYONO

  DOI：——

  日期：——
• JPH03284662A
  申请人：——

  公开号：JPH03284662A

  公开（公告）日：1991-12-16
• 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.