3-methoxy-6,7,8,9,10,11-hexahydroazocino[1,2-a]benzimidazole | 1059200-74-6

• 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: 3-methoxy-6,7,8,9,10,11-hexahydroazocino[1,2-a]benzimidazole
• 英文别名: 3-methoxy-6,7,8,9,10,11-hexahydro-6H-azocino[1,2-a]benzimidazole
• CAS: 1059200-74-6
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: SENZIVFOTPISMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-[2-(azocan-1-yl)-5-methoxyphenyl]acetamide 在 甲酸 、 双氧水 作用下， 反应 1.0h， 以66%的产率得到3-methoxy-6,7,8,9,10,11-hexahydroazocino[1,2-a]benzimidazole
  参考文献：
  名称：

  Synthesis of seven- and eight-membered [1,2-a] alicyclic ring-fused benzimidazoles and 3-aziridinylazepino[1,2-a]benzimidazolequinone as a potential antitumour agent

  摘要：

  Azepino and azocino[1,2-a]benzimidazoles were obtained either by treatment of 1-nitrophenyl-2-azacycloalkanes via a one-pot catalytic hydrogenation/acetylation or by treatment of the acetamides generated in the latter reaction with performic acid. This represents the first facile synthesis of eight-membered (1,2-a] alicyclic ring-fused benzimidazoles. 3-Methoxy-azepino[1,2-a]benzimidazole was elaborated to the novel potential cytotoxin, 3-(N-aziridinyl)-7,8,9,10-tetrahydro-6H-azepino[1,2-a]benz-imidazole-1,4-dione. The synthesis included clarification of the reactivity of methoxy-substituted benzimidazoles towards nitration. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.121

文献信息

• Greener synthesis using hydrogen peroxide in ethyl acetate of alicyclic ring-fused benzimidazoles and anti-tumour benzimidazolequinones
  作者：Martin Sweeney、Michael Gurry、Lee-Ann J. Keane、Fawaz Aldabbagh

  DOI：10.1016/j.tetlet.2017.07.102

  日期：2017.9

  Environmentally-friendly and cost effective hydrogen peroxide in ethyl acetate was used to prepare in high yields pyrrolo[1,2-a]benzimidazoles from commercial o-(pyrrolidin-1-yl)anilines without the requirement for organic-aqueous extraction and chromatography. Six, seven and eight membered ring-fused analogues were similarly obtained in high yields with methanesulfonic acid required for the pyrido[1

  使用环境友好且经济高效的乙酸乙酯中的过氧化氢，无需有机水萃取和色谱法即可从商业邻-（吡咯烷基-1-基）苯胺制备高收率的吡咯并[1,2- a ]苯并咪唑。用吡啶[1,2- a ]苯并咪唑所需的甲磺酸，以高收率相似地获得了六，七和八元环稠合的类似物。通过3,6-二甲氧基-2-（环氨基）苯胺的环化，可以高产率获得抗肿瘤苯并咪唑醌衍生物。
• Synthesis of seven- and eight-membered [1,2-a] alicyclic ring-fused benzimidazoles and 3-aziridinylazepino[1,2-a]benzimidazolequinone as a potential antitumour agent
  作者：Karen Fahey、Fawaz Aldabbagh

  DOI：10.1016/j.tetlet.2008.06.121

  日期：2008.9

  Azepino and azocino[1,2-a]benzimidazoles were obtained either by treatment of 1-nitrophenyl-2-azacycloalkanes via a one-pot catalytic hydrogenation/acetylation or by treatment of the acetamides generated in the latter reaction with performic acid. This represents the first facile synthesis of eight-membered (1,2-a] alicyclic ring-fused benzimidazoles. 3-Methoxy-azepino[1,2-a]benzimidazole was elaborated to the novel potential cytotoxin, 3-(N-aziridinyl)-7,8,9,10-tetrahydro-6H-azepino[1,2-a]benz-imidazole-1,4-dione. The synthesis included clarification of the reactivity of methoxy-substituted benzimidazoles towards nitration. (C) 2008 Elsevier Ltd. All rights reserved.