4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide | 368838-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide
• 英文别名: 7-bromo-5-nitro-3-oxidospiro[benzimidazol-1-ium-2,1'-cyclohexane] 1-oxide
• CAS: 368838-71-5
• 化学式: C₁₂H₁₂BrN₃O₄
• 分子量: 342.149
• InChiKey: AFVFWBAQBNBDFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  92.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide 以 氘代氯仿 为溶剂， 反应 72.0h， 生成 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1-oxide
  参考文献：
  名称：

  Reaction of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with electrophilic reagents: Bromine and nitric acid

  摘要：

  Reactions of 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide with bromine and nitric acid lead to the electrophilic substitution of the hydrogen atom in the meta-position with respect to the nitro group. At thebromination the primarily formed 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide when kept in the solution loses an oxygen atom forming 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1-oxide and an isomerization product, 8-bromo-6-nitrospiro[3H-[2,1,4]benzoxadiazine-3,1'-cyclohexane] 4-oxide. The latter exposed to light turns into 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide. The reaction of the initial 1,3-dioxide with nitric acid afforded 4,6-dinitrospiro[benzimidazole-2,1'-cyclohexan]-7-ol 1-oxide whose heating in o-dichlorobenzene resulted in 3,5-dinitro-1,8-diazatricyclo[7.5.0.0(2,7)] tetradeca-2(7),3,5,8-tetraen-6-ol.

  DOI：

  10.1134/s1070428013080198
• 作为产物：
  描述：

  8-bromo-6-nitrospiro[3H-[2,1,4]benzoxadiazine-3,1'-cyclohexane] 4-oxide 以 苯 为溶剂， 反应 168.0h， 以53%的产率得到4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide
  参考文献：
  名称：

  Reaction of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with electrophilic reagents: Bromine and nitric acid

  摘要：

  Reactions of 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide with bromine and nitric acid lead to the electrophilic substitution of the hydrogen atom in the meta-position with respect to the nitro group. At thebromination the primarily formed 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide when kept in the solution loses an oxygen atom forming 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1-oxide and an isomerization product, 8-bromo-6-nitrospiro[3H-[2,1,4]benzoxadiazine-3,1'-cyclohexane] 4-oxide. The latter exposed to light turns into 4-bromo-6-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide. The reaction of the initial 1,3-dioxide with nitric acid afforded 4,6-dinitrospiro[benzimidazole-2,1'-cyclohexan]-7-ol 1-oxide whose heating in o-dichlorobenzene resulted in 3,5-dinitro-1,8-diazatricyclo[7.5.0.0(2,7)] tetradeca-2(7),3,5,8-tetraen-6-ol.

  DOI：

  10.1134/s1070428013080198