N-(3-nitrophenyl)spiro[benzimidazole-2,1'-cyclohexan]-5-amine 1-oxide | 1373439-42-9

• 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: N-(3-nitrophenyl)spiro[benzimidazole-2,1'-cyclohexan]-5-amine 1-oxide
• 英文别名: N-(3-nitrophenyl)spiro[benzimidazole-2,1'-cyclo-hexan]-5-amine 1-oxide；N-(3-nitrophenyl)-1-oxidospiro[benzimidazol-1-ium-2,1'-cyclohexane]-5-amine
• CAS: 1373439-42-9
• 化学式: C₁₈H₁₈N₄O₃
• 分子量: 338.366
• InChiKey: JEZJEGPTCLQMAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-硝基苯胺盐酸盐 、 5-nitrospiro[2H-benzimidazole-2,1'-cyclohexane]-1,3-dioxide 以 甲醇 为溶剂， 反应 4.0h， 以51%的产率得到N-(3-nitrophenyl)spiro[benzimidazole-2,1'-cyclohexan]-5-amine 1-oxide
  参考文献：
  名称：

  Reactions of 5-nitrospiro[benzimidazole-2,1′-cyclohexane] 1,3-dioxide with nucleophiles

  摘要：

  Reactions of 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide with aliphatic amines and sodium hydroxide resulted in removal of one N-oxide oxygen atom and formation of 4-alkylamino- or 4-hydroxy-substituted 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1-oxides, respectively. The title compound reacted with ammonia and methylamine in the presence of MnO2 with conservation of both N-oxide moieties, and the products were 4-amino- and 4-methylamino-5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxides. The reactions with aromatic amines were accompanied by removal of both N-oxide oxygen atoms with formation of N-aryl-5-nitrospiro[benzimidazole-2,1'-cyclohexane]-4-amines. In the reactions of 5-nitrospiro[ benzimidazole-2,1'-cyclohexane] 1,3-dioxide with sodium azide and aromatic amine hydrochlorides nucleophilic replacement of the 5-nitro group by azido or arylamino occurred, in the first case both N-oxide fragments being conserved. The reactions with aromatic amine hydrochlorides afforded N-aryl-5-nitrospiro[benzimidazole-2,1'-cyclohexan]-4-amine 1-oxides. Treatment of 5-nitrospiro[benzimidazole-2,1'-cyclohexane] 1,3-dioxide with sodium cyanide led to the formation of 5-oxo-3,5-dihydrospiro[benzimidazole-2,1'-cyclohexane]-4-carbonitrile 1-oxide.

  DOI：

  10.1134/s1070428012030116