(3-methylbenzyl)(trifluoromethyl)sulfane | 1444123-77-6

• 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: (3-methylbenzyl)(trifluoromethyl)sulfane
• 英文别名: 1-Methyl-3-(trifluoromethylsulfanylmethyl)benzene；1-methyl-3-(trifluoromethylsulfanylmethyl)benzene
• CAS: 1444123-77-6
• 化学式: C₉H₉F₃S
• 分子量: 206.232
• InChiKey: OZAACEDRMIJOSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-methylbenzyl)(trifluoromethyl)sulfane 、 丙烯酸乙酯 在 2,2'-联吡啶 、 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 copper diacetate 作用下， 反应 12.0h， 以98%的产率得到ethyl 4-methyl-2-((trifluoromethylthio)methyl)cinnamate
  参考文献：
  名称：

  Ir(III)-Catalyzed Mono-Olefination of Aryl C–H Bonds Using −SCF₃ as a Weak Directing Group

  摘要：

  The trifluoromethylthionyl group (-SCF3) is an efficient weak directing group for Ir(III)-catalyzed aryl C-H olefination. Various trifluoromethylthioethers provide high levels of mono-olefination products in good to excellent yields under mild conditions with a 2,2'-bipyridine ligand or AgBF4 as an additive. Mechanistic studies indicate the C-H cleavage is the rate-determining step. The directing group ability of the -SCF3 group is benchmarked against several other weak directing groups by competition experiments under Ir(III)-catalyzed conditions.

  DOI：

  10.1021/acs.orglett.9b03125
• 作为产物：
  描述：

  3-甲基苄溴 、 (三氟甲硫基)银(I) 在 四丁基碘化铵 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以70%的产率得到(3-methylbenzyl)(trifluoromethyl)sulfane
  参考文献：
  名称：

  Ir(III)-Catalyzed Mono-Olefination of Aryl C–H Bonds Using −SCF₃ as a Weak Directing Group

  摘要：

  The trifluoromethylthionyl group (-SCF3) is an efficient weak directing group for Ir(III)-catalyzed aryl C-H olefination. Various trifluoromethylthioethers provide high levels of mono-olefination products in good to excellent yields under mild conditions with a 2,2'-bipyridine ligand or AgBF4 as an additive. Mechanistic studies indicate the C-H cleavage is the rate-determining step. The directing group ability of the -SCF3 group is benchmarked against several other weak directing groups by competition experiments under Ir(III)-catalyzed conditions.

  DOI：

  10.1021/acs.orglett.9b03125

文献信息

• Room temperature nucleophilic trifluoromethylthiolation of benzyl bromides with (bpy)Cu(SCF3)
  作者：Dedao Kong、Zhou Jiang、Shaogang Xin、Zhengshuai Bai、Yaofeng Yuan、Zhiqiang Weng

  DOI：10.1016/j.tet.2013.05.073

  日期：2013.7

  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.
• Ir(III)-Catalyzed Mono-Olefination of Aryl C–H Bonds Using −SCF₃ as a Weak Directing Group
  作者：Rui-Peng Bao、Xian Chen、Chen Li、Dong-Hui Wang

  DOI：10.1021/acs.orglett.9b03125

  日期：2019.10.4

  The trifluoromethylthionyl group (-SCF3) is an efficient weak directing group for Ir(III)-catalyzed aryl C-H olefination. Various trifluoromethylthioethers provide high levels of mono-olefination products in good to excellent yields under mild conditions with a 2,2'-bipyridine ligand or AgBF4 as an additive. Mechanistic studies indicate the C-H cleavage is the rate-determining step. The directing group ability of the -SCF3 group is benchmarked against several other weak directing groups by competition experiments under Ir(III)-catalyzed conditions.