5-nitrospiro[1H-indole-1,1'-piperidinium]-2-thiolate | 1073497-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-nitrospiro[1H-indole-1,1'-piperidinium]-2-thiolate
• 英文别名: 5'-Nitrospiro[azinan-1-ium-1,1'-indol-1-ium]-2'-thiolate
• CAS: 1073497-92-3
• 化学式: C₁₃H₁₄N₂O₂S
• 分子量: 262.332
• InChiKey: QRUXZVMUXXLTNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  哌啶 、 4-(2-chloro-5-nitrophenyl)-1,2,3-thiadiazole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以17%的产率得到5-nitrospiro[1H-indole-1,1'-piperidinium]-2-thiolate
  参考文献：
  名称：

  Synthesis of 1,1-Dialkylindolium-2-thiolates via Base-Induced Transformation of 4-(2-Chloro-5-nitrophenyl)-1,2,3-thiadiazole in the Presence of Secondary Amines

  摘要：

  4-(2-Chloro-5-nitrophenyl)-1,2,3-thiadiazole undergoes ring-opening to produce a thioketene intermediate that reacts with secondary amines forming 2-(2-chloro-5-nitrophenyl)-N,N-dialkylthioacetamides. Intramolecular cyclization of these thioamides via nucleophilic substitution of the halogen on the aromatic ring affords nonaromatic 1,1-dialkylindolium-2-thiolates instead of the expected aromatic N,N-dialkylaminobenzo[b]thiophenes.

  DOI：

  10.1021/jo801801y

文献信息

• Synthesis of 1,1-Dialkylindolium-2-thiolates via Base-Induced Transformation of 4-(2-Chloro-5-nitrophenyl)-1,2,3-thiadiazole in the Presence of Secondary Amines
  作者：Dmitry A. Androsov

  DOI：10.1021/jo801801y

  日期：2008.11.7

  4-(2-Chloro-5-nitrophenyl)-1,2,3-thiadiazole undergoes ring-opening to produce a thioketene intermediate that reacts with secondary amines forming 2-(2-chloro-5-nitrophenyl)-N,N-dialkylthioacetamides. Intramolecular cyclization of these thioamides via nucleophilic substitution of the halogen on the aromatic ring affords nonaromatic 1,1-dialkylindolium-2-thiolates instead of the expected aromatic N,N-dialkylaminobenzo[b]thiophenes.