5-azido-1,2,4-triazol-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-azido-1,2,4-triazol-3-one
• 英文别名: 3-Azido-1,4-dihydro-1,2,4-triazol-5-one；3-azido-1,4-dihydro-1,2,4-triazol-5-one
• 化学式: C₂H₂N₆O
• 分子量: 126.077
• InChiKey: BHNNOPHELNDKIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 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：
  67.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氨基-2,4-二氢-[1,2,4]噻唑-3-酮 在 盐酸 、 sodium nitrite 作用下， 反应 1.0h， 以55%的产率得到5-azido-1,2,4-triazol-3-one
  参考文献：
  名称：

  Synthesis of [3-14C]- and [5-14C]-labelled 5-nitro-1,2,4-triazol-3-one (NTO) and study of its chemical decomposition

  摘要：

  The chemical decomposition of NTO 1 and its corresponding amine ATO 2 was investigated. To make easier the identification of the decomposition products, we synthesized C-14-labelled NTO and ATO. Our results confirmed the high stability of the NTO triazolone ring. Its scission can be achieved partially by sulfuric acid under intensive heat and pressure. The triazolone ring of ATO was cleaved in alkaline solution. Carbon dioxide is evolved leaving a polar compound assumed to be aminoguanidine. The deamination of ATO was achieved by nitrosation. In dilute HCl (0.15N), 2 equivalents of NO2- lead to the triazolone: Lb, through a radical de-diazotation of the diazo intermediate. With 3 to 10 equivalents of NO2-, the nitrosation leads exclusively to the azide 6.

  DOI：

  10.1002/(sici)1099-1344(199912)42:12<1203::aid-jlcr276>3.0.co;2-f