5-chloro-3-(((trifluoromethyl)thio)methyl)benzo[b]thiophene | 1444123-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5-chloro-3-(((trifluoromethyl)thio)methyl)benzo[b]thiophene
• 英文别名: 5-Chloro-3-(trifluoromethylsulfanylmethyl)-1-benzothiophene；5-chloro-3-(trifluoromethylsulfanylmethyl)-1-benzothiophene
• CAS: 1444123-97-0
• 化学式: C₁₀H₆ClF₃S₂
• 分子量: 282.738
• InChiKey: OEOBPUOVJKPKNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-溴甲基-5-氯苯并噻吩 、 三氟甲基硫醇（2,2-联吡啶）铜（I） 以 乙腈 为溶剂， 反应 8.0h， 以97%的产率得到5-chloro-3-(((trifluoromethyl)thio)methyl)benzo[b]thiophene
  参考文献：
  名称：

  Room temperature nucleophilic trifluoromethylthiolation of benzyl bromides with (bpy)Cu(SCF3)

  摘要：

  The nudeophilic trifluoromethylthiolation of benzyl bromides using (bpy)Cu(SCF3) gave the desired products of benzyl trifluoromethyl sulfides in good to excellent yields. A diverse set of important functional groups including cyano, nitro, ester, alkoxy, halide, and heterocyclic groups can be well tolerated in the protocol. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.073

文献信息

• Difluorocarbene‐Derived Trifluoromethylthiolation and [ ¹⁸ F]Trifluoromethylthiolation of Aliphatic Electrophiles
  作者：Jian Zheng、Lu Wang、Jin‐Hong Lin、Ji‐Chang Xiao、Steven H. Liang

  DOI：10.1002/anie.201505446

  日期：2015.11.2

  The first trifluoromethylthiolation and [18F]trifluoromethylthiolation of alkyl electrophiles with in situ generated difluorocarbene in the presence of elemental sulfur and external (radioactive) fluoride ion is described. This transition‐metal‐free approach is high yielding, compatible with a variety of functional groups, and operated under mild reaction conditions. The conceptual advantage of this

  描述了在元素硫和外部（放射性）氟离子存在下，用原位生成的二氟卡宾对烷基亲电试剂进行的第一次三氟甲基硫醇化和[ 18 F]三氟甲基硫醇化。这种无过渡金属的方法收率高，可与各种官能团兼容，并且可在温和的反应条件下操作。这种外源氟化物介导的转化的概念优势使空前的[ 18 F] CF 3 S标记分子从最常用的[ 18 F]氟离子合成成为可能。快速的放射化学反应时间（≤1分钟）和高的官能团耐受性允许接触各种脂肪族[ 18 F] CF 3S化合物产量高。
• Ph3P+CF2CO2− as an F− and :CF2 source for trifluoromethylthiolation of alkyl halides
  作者：Zhuo Liu、Jin Long、Xuan Xiao、Jin-Hong Lin、Xing Zheng、Ji-Chang Xiao、Yu-Cai Cao

  DOI：10.1016/j.cclet.2018.11.013

  日期：2019.3

  As trifluoromethylthiolation has received increasing attention recently, many CF3S-reagents and trifluoromethylthiolation methods have been developed. Herein we describe trifluoromethylthiolation of alkyl halides by using Ph3P+CF2CO2 as a fluoride and difluorocarbene source. Difluorocarbene is a versatile intermediate, but its side reactions are usually ignored and the by-products would therefore be discarded. In this work, a side reaction of difluorocarbene, the generation of a fluoride anion from difluorocarbene, was developed into a synthetic tool. Although the trifluoromethylthiolation reaction involved multi-sequential steps, the cleavage of C-F bond, the formation of CF2=S bond, F-C(S)F-2 bond, and C-SCF3 bond, the conversion proceeded fast and was completed within 10 min. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.