S-difluoromethyl N-(p-methylphenyl)benzenecarbothioimidate

• 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: S-difluoromethyl N-(p-methylphenyl)benzenecarbothioimidate
• 英文别名: alpha-(Difluoromethylthio)-N-(4-methylphenyl)benzenemethaneimine；difluoromethyl N-(4-methylphenyl)benzenecarboximidothioate
• 化学式: C₁₅H₁₃F₂NS
• 分子量: 277.338
• InChiKey: FGMHLQLMYVHSST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯并-p-甲苯胺 在 劳森试剂 、 1,8-双二甲氨基萘 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.67h， 生成 S-difluoromethyl N-(p-methylphenyl)benzenecarbothioimidate
  参考文献：
  名称：

  Organocatalytic, difluorocarbene-based S-difluoromethylation of thiocarbonyl compounds

  摘要：

  Upon treatment with trimethylsilyl 2,2-difluoro-2-fluorosulfonylacetate (TFDA) and a catalytic amount of N,N,N',N'-tetramethyl-1,8-diaminonaphthalene, secondary thioamides and thiocarbamates undergo selective difluoromethylation on the sulfur atom to give S-difluoromethyl thioimidates and thioiminocarbonates in good yields, respectively. This is the first report on the synthesis of acyclic difluoromethyl thioimidates and thioiminocarbonates. The key for S-difluoromethylation is the organocatalytic generation of difluorocarbene (:CF2) under mild conditions, which prevents decomposition of the substrates. This process provides an efficient approach to pharmaceuticals and agrochemicals bearing a difluoromethylsulfanyl group, starting from widely available thiocarbonyl compounds. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.08.013

文献信息

• Organocatalytic, difluorocarbene-based S-difluoromethylation of thiocarbonyl compounds
  作者：Kohei Fuchibe、Masaki Bando、Ryo Takayama、Junji Ichikawa

  DOI：10.1016/j.jfluchem.2014.08.013

  日期：2015.3

  Upon treatment with trimethylsilyl 2,2-difluoro-2-fluorosulfonylacetate (TFDA) and a catalytic amount of N,N,N',N'-tetramethyl-1,8-diaminonaphthalene, secondary thioamides and thiocarbamates undergo selective difluoromethylation on the sulfur atom to give S-difluoromethyl thioimidates and thioiminocarbonates in good yields, respectively. This is the first report on the synthesis of acyclic difluoromethyl thioimidates and thioiminocarbonates. The key for S-difluoromethylation is the organocatalytic generation of difluorocarbene (:CF2) under mild conditions, which prevents decomposition of the substrates. This process provides an efficient approach to pharmaceuticals and agrochemicals bearing a difluoromethylsulfanyl group, starting from widely available thiocarbonyl compounds. (C) 2014 Elsevier B.V. All rights reserved.