1-allyl-2-amino-3-(2-oxo-2-phenylethyl)benzimidazolium bromide | 202117-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-allyl-2-amino-3-(2-oxo-2-phenylethyl)benzimidazolium bromide
• 英文别名: 1-Allyl-2-amino-3-(2-oxo-2-phenylethyl)benz-imidazolium bromide；2-(2-amino-3-prop-2-enylbenzimidazol-1-ium-1-yl)-1-phenylethanone;bromide
• CAS: 202117-58-6
• 化学式: Br*C₁₈H₁₈N₃O
• 分子量: 372.264
• InChiKey: SVTPOMLTFRFHBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.42
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-allyl-2-amino-3-(2-oxo-2-phenylethyl)benzimidazolium bromide 在 氨 作用下， 以 水 为溶剂， 反应 3.25h， 生成 9-allyl-2-phenylimidazo[1,2-a]benzimidazole
  参考文献：
  名称：

  Imidazo[1,2-a]benzimidazole derivatives: XXIX. 1-allyl-2-amino-3-acylmethylbenzimidazolium halides and syntheses on their base

  摘要：

  Cyclization of 1-allyl-2-amino-3-acylmethylbenzimidazolium halides under alkaline conditions gave 9-allyl-substituted imidazo[1,2-a]benzimidazoles. Cyclization of the same compounds on heating in concentrated hydrobromic acid was accompanied by addition of hydrogen bromide at the exocyclic double bond. Competing cyclizations with participation of the 1-(2-bromopropyl) and 3-acylmethyl substituents in 2-imino-2,3-dihydro-1H-benzimidazole were studied. Functionalization of the imidazo[1,2-a]benzimidazole system was performed via introduction of substituents into the 3-position and replacement of bromine in the 2-bromopropyl group in the 9-position.

  DOI：

  10.1134/s1070428011090168
• 作为产物：
  描述：

  1-allyl-1H-benzimidazol-2-amine 、 2-溴苯乙酮 以 丙酮 为溶剂， 以97%的产率得到1-allyl-2-amino-3-(2-oxo-2-phenylethyl)benzimidazolium bromide
  参考文献：
  名称：

  Imidazo[1,2-a]benzimidazole derivatives: XXIX. 1-allyl-2-amino-3-acylmethylbenzimidazolium halides and syntheses on their base

  摘要：

  Cyclization of 1-allyl-2-amino-3-acylmethylbenzimidazolium halides under alkaline conditions gave 9-allyl-substituted imidazo[1,2-a]benzimidazoles. Cyclization of the same compounds on heating in concentrated hydrobromic acid was accompanied by addition of hydrogen bromide at the exocyclic double bond. Competing cyclizations with participation of the 1-(2-bromopropyl) and 3-acylmethyl substituents in 2-imino-2,3-dihydro-1H-benzimidazole were studied. Functionalization of the imidazo[1,2-a]benzimidazole system was performed via introduction of substituents into the 3-position and replacement of bromine in the 2-bromopropyl group in the 9-position.

  DOI：

  10.1134/s1070428011090168

文献信息

• Imidazo[1,2-a]benzimidazole derivatives: XXIX. 1-allyl-2-amino-3-acylmethylbenzimidazolium halides and syntheses on their base
  作者：V. A. Anisimova、I. E. Tolpygin

  DOI：10.1134/s1070428011090168

  日期：2011.9

  Cyclization of 1-allyl-2-amino-3-acylmethylbenzimidazolium halides under alkaline conditions gave 9-allyl-substituted imidazo[1,2-a]benzimidazoles. Cyclization of the same compounds on heating in concentrated hydrobromic acid was accompanied by addition of hydrogen bromide at the exocyclic double bond. Competing cyclizations with participation of the 1-(2-bromopropyl) and 3-acylmethyl substituents in 2-imino-2,3-dihydro-1H-benzimidazole were studied. Functionalization of the imidazo[1,2-a]benzimidazole system was performed via introduction of substituents into the 3-position and replacement of bromine in the 2-bromopropyl group in the 9-position.