N'-cyclohexyl-N,N-tetramethylenethiocarbamoylsulfenamide | 66552-57-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N'-cyclohexyl-N,N-tetramethylenethiocarbamoylsulfenamide
• 英文别名: (cyclohexylamino) pyrrolidine-1-carbodithioate
• CAS: 66552-57-6
• 化学式: C₁₁H₂₀N₂S₂
• 分子量: 244.425
• InChiKey: ITQJPCZLKVOACT-UHFFFAOYSA-N

物化性质

• 熔点：
  59-61 °C
• 沸点：
  351.0±25.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  15.27
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  间溴硝基苯 、 N'-cyclohexyl-N,N-tetramethylenethiocarbamoylsulfenamide 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以66%的产率得到2-bromo-N-cyclohexyl-4-nitroaniline
  参考文献：
  名称：

  Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen:  Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

  摘要：

  A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The sigma adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkryl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of amination.

  DOI：

  10.1021/jo970582b
• 作为产物：
  描述：

  环己胺 、 sodium pyrrolidine-N-carbodithioate 在 碘 作用下， 生成 N'-cyclohexyl-N,N-tetramethylenethiocarbamoylsulfenamide
  参考文献：
  名称：

  Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen:  Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

  摘要：

  A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The sigma adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkryl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of amination.

  DOI：

  10.1021/jo970582b

文献信息

• FAID-ALLAH, HASSAN M., REV. ROUM. CHIM., 33,(1988) N, C. 815-822
  作者：FAID-ALLAH, HASSAN M.

  DOI：——

  日期：——
• FAID-ALLAH, HASSAN M., EGYPT. J. CHEM., 31,(1988) N, C. 295-307
  作者：FAID-ALLAH, HASSAN M.

  DOI：——

  日期：——