4-fluoro-3,5-bismethylthiobenzoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-fluoro-3,5-bismethylthiobenzoic acid
• 英文别名: 4-Fluoro-3,5-bis(methylthio)benzoic acid；4-fluoro-3,5-bis(methylsulfanyl)benzoic acid
• 化学式: C₉H₉FO₂S₂
• 分子量: 232.3
• InChiKey: CJPYZXUJMNOTKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二甲基二硫 、 对氟苯甲酸 在 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以56%的产率得到4-fluoro-3-methylthiobenzoic acid
  参考文献：
  名称：

  The First Regioselective Metalation and Functionalization of Unprotected 4-Halobenzoic Acids

  摘要：

  By treatment with s-BuLi, s-BuLi/TMEDA, or t-BuLi at similar to-78 degreesC, 4-fluoro- and 4-chlorobenzoic acids (1a,b) are metalated preferentially in the position adjacent to the carboxylate. A complete reversal in regioselectivity is observed for 1a when treated with LTMP; a sequential process involving a rapid intraaggregate lithiation through a quasi dianion complex "QUADAC" is postulated to explain the unusual reactivity of Me2S2 and I-2.

  DOI：

  10.1021/jo0483365

文献信息

• The First Regioselective Metalation and Functionalization of Unprotected 4-Halobenzoic Acids
  作者：Frédéric Gohier、Anne-Sophie Castanet、Jacques Mortier

  DOI：10.1021/jo0483365

  日期：2005.2.1

  By treatment with s-BuLi, s-BuLi/TMEDA, or t-BuLi at similar to-78 degreesC, 4-fluoro- and 4-chlorobenzoic acids (1a,b) are metalated preferentially in the position adjacent to the carboxylate. A complete reversal in regioselectivity is observed for 1a when treated with LTMP; a sequential process involving a rapid intraaggregate lithiation through a quasi dianion complex "QUADAC" is postulated to explain the unusual reactivity of Me2S2 and I-2.