(2-methylbenzyl)(trifluoromethyl)sulfane | 1612253-22-1

• 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: (2-methylbenzyl)(trifluoromethyl)sulfane
• 英文别名: 1-Methyl-2-(trifluoromethylsulfanylmethyl)benzene
• CAS: 1612253-22-1
• 化学式: C₉H₉F₃S
• 分子量: 206.232
• InChiKey: JPLDQHCYKQAYQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2-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95%的产率得到ethyl 3-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：

  (三氟甲硫基)银(I) 、 2-甲基苄溴 在 四丁基碘化铵 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以66%的产率得到(2-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

• 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。
• Copper-Catalyzed Direct Trifluoromethylthiolation of Benzylic C–H Bonds via Nondirected Oxidative C(sp³)–H Activation
  作者：Chao Chen、Xiu-Hua Xu、Bin Yang、Feng-Ling Qing

  DOI：10.1021/ol501400u

  日期：2014.6.20

  A copper-catalyzed trifluoromethylthiolation of benzylic sp(3) C-H bonds was developed via nondirected oxidative C-H activation using readily prepared and stable AgSCF3. This reaction provides a novel and straightforward method for the preparation of various benzyl trifluoromethyl sulfides.