S-pyrimidin-2-yl-thiohydroxylamine | 3993-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: S-pyrimidin-2-yl-thiohydroxylamine
• 英文别名: S-Pyrimidin-2-yl-(thiohydroxylamine)；S-pyrimidin-2-ylthiohydroxylamine
• CAS: 3993-82-6
• 化学式: C₄H₅N₃S
• 分子量: 127.17
• InChiKey: RJDBTOSSFOEORB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-巯基嘧啶 在 sodium hypochlorite 、 氨 作用下， 反应 0.5h， 生成 S-pyrimidin-2-yl-thiohydroxylamine
  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