1,2-bis(1-ethyl-1H-1,2,3-triazol-4-yl)diazene 1-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: 1,2-bis(1-ethyl-1H-1,2,3-triazol-4-yl)diazene 1-oxide
• 英文别名: (1-ethyltriazol-4-yl)-(1-ethyltriazol-4-yl)imino-oxidoazanium
• 化学式: C₈H₁₂N₈O
• mdl: MFCD06616934
• 分子量: 236.236
• InChiKey: XVIJGAOKSCPMAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-ethyl-4-nitro-1,2,3-triazole 在 sodium hydroxide 、 氢化铝 作用下， 以 乙醇 为溶剂， 以75%的产率得到1,2-bis(1-ethyl-1H-1,2,3-triazol-4-yl)diazene 1-oxide
  参考文献：
  名称：

  Trifluoromethyl Sulfones and Perfluoroalkanesulfonamides of the Azole Series

  摘要：

  2-Phenyl-4-trifluoromethylsulfonylmethyl-2H-1,2,3-triazole was synthesized from 4-bromomethyl-2-phenyl-2H- 1,2,3-triazole and sodium trifluoromethanesulfinate CF3SO2Na. 1(2)-Ethyl-4-nitro-1 (2)H-1,2,3-triazoles and 4-nitro-2-phenyl-2H-1,2,3-triazole were reduced to the corresponding amines. Intermediate 1,2-bis(1-ethyl-1H-1,2,3-triazol-4-yl)diazene 1-oxide exists as a mixture of syn and anti isomers, the former being stabilized via formation of a strong intramolecular hydrogen bond. The reduction of 2-ethyl-4-nitro-2H-1,2,3-triazole in the presence of HCl afforded the target 4-amino-2-ethyl-2H-1,2,3-triazole and also 4-amino-5chloro-2-ethyl-2H-1,2,3-triazole. Treatment of alkyl-substituted 4-amino-1.2,3-triazoles with trifluoromethanesulfonyl chloride and pentafluoroethanesulfon I chloride gave N-triazolyl-substituted trifluoromethane- and pentafluoroethanesulfonamides and -imides.

  DOI：

  10.1023/b:rujo.0000034977.74026.b3

文献信息

• Trifluoromethyl Sulfones and Perfluoroalkanesulfonamides of the Azole Series
  作者：V. I. Meshcheryakov、B. A. Shainyan

  DOI：10.1023/b:rujo.0000034977.74026.b3

  日期：2004.3

  2-Phenyl-4-trifluoromethylsulfonylmethyl-2H-1,2,3-triazole was synthesized from 4-bromomethyl-2-phenyl-2H- 1,2,3-triazole and sodium trifluoromethanesulfinate CF3SO2Na. 1(2)-Ethyl-4-nitro-1 (2)H-1,2,3-triazoles and 4-nitro-2-phenyl-2H-1,2,3-triazole were reduced to the corresponding amines. Intermediate 1,2-bis(1-ethyl-1H-1,2,3-triazol-4-yl)diazene 1-oxide exists as a mixture of syn and anti isomers, the former being stabilized via formation of a strong intramolecular hydrogen bond. The reduction of 2-ethyl-4-nitro-2H-1,2,3-triazole in the presence of HCl afforded the target 4-amino-2-ethyl-2H-1,2,3-triazole and also 4-amino-5chloro-2-ethyl-2H-1,2,3-triazole. Treatment of alkyl-substituted 4-amino-1.2,3-triazoles with trifluoromethanesulfonyl chloride and pentafluoroethanesulfon I chloride gave N-triazolyl-substituted trifluoromethane- and pentafluoroethanesulfonamides and -imides.