5-chloro-1-ethenyl-3-nitro-1,2,4-triazole | 373641-32-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-chloro-1-ethenyl-3-nitro-1,2,4-triazole
• CAS: 373641-32-8
• 化学式: C₄H₃ClN₄O₂
• 分子量: 174.546
• InChiKey: ZMSCTQZMFOFWMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.85
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-chloro-1-ethenyl-3-nitro-1,2,4-triazole 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-hydrazino-3-nitro-1-vinyl-1,2,4-triazole
  参考文献：
  名称：

  摘要：

  A series of 5-substituted 3-nitro-1-vinyl-1,2,4-triazoles were synthesized by alkaline treatment of the corresponding 1-(2-haloethyl- or 2-nitroxyethyl)-3-nitro-1,2,4-triazoles and by transvinylation of NH acids of the same series with vinyl acetate. The scope of applicability of the transvinylation procedure was established with respect to the azole pK(a) value. The vinylic double bond on the nitrogen was shown to be inactive toward both nucleophilic and electrophilic reagents, whereas the halogen atom in position 5 exhibits enhanced reactivity. The latter factor provides the possibility for versatile structural modification via nucleophilic replacement of the 5-halogen atom by various groups, including triazolate ion.

  DOI：

  10.1023/a:1012460103654
• 作为产物：
  描述：

  乙酸乙烯酯 、 5-氯-3-硝基-1H-1,2,4-三唑 在 硫酸 、 对苯二酚 、 mercury(II) oxide 作用下， 以65%的产率得到5-chloro-1-ethenyl-3-nitro-1,2,4-triazole
  参考文献：
  名称：

  摘要：

  A series of 5-substituted 3-nitro-1-vinyl-1,2,4-triazoles were synthesized by alkaline treatment of the corresponding 1-(2-haloethyl- or 2-nitroxyethyl)-3-nitro-1,2,4-triazoles and by transvinylation of NH acids of the same series with vinyl acetate. The scope of applicability of the transvinylation procedure was established with respect to the azole pK(a) value. The vinylic double bond on the nitrogen was shown to be inactive toward both nucleophilic and electrophilic reagents, whereas the halogen atom in position 5 exhibits enhanced reactivity. The latter factor provides the possibility for versatile structural modification via nucleophilic replacement of the 5-halogen atom by various groups, including triazolate ion.

  DOI：

  10.1023/a:1012460103654