8,11-dimethoxy-5-methyl-5,6-dihydrobenzimidazo[2,1-a]isoquinoline | 1187828-50-7

• 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: 8,11-dimethoxy-5-methyl-5,6-dihydrobenzimidazo[2,1-a]isoquinoline
• 英文别名: 8,11-Dimethoxy-5-methyl-5,6-dihydrobenzimidazolo[2,1-a]isoquinoline；8,11-dimethoxy-5-methyl-5,6-dihydrobenzimidazolo[2,1-a]isoquinoline
• CAS: 1187828-50-7
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: QMLJPWFSMJIBCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8,11-dimethoxy-5-methyl-5,6-dihydrobenzimidazo[2,1-a]isoquinoline 在 氢溴酸 、 iron(III) chloride 作用下， 以 水 为溶剂， 反应 21.0h， 以82%的产率得到5-methyl-5,6-dihydrobenzimidazo[2,1-a]isoquinoline-8,11-dione
  参考文献：
  名称：

  Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations

  摘要：

  The preparation of alicyclic ring-fused tetracyclic and pentacyclic benzimidazoles containing one and two fused aryl rings, respectively, is achieved conveniently in three steps, including Bu3SnH-mediated 6-exo-trig cyclization of sigma-aryl radicals generated from 1-allyl-2-(omega-bromoaryl)benzimidazoles. Inclusion Of 4,7-dimethoxy substituents on the radical precursors allows access to aryl ring-fused benzimidazolequitiones, a Unique family of potential bioreductive anti-cancer agents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.023
• 作为产物：
  描述：

  2-(2-Bromophenyl)-4,7-dimethoxy-1-prop-2-enylbenzimidazole 在 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以67%的产率得到8,11-dimethoxy-5-methyl-5,6-dihydrobenzimidazo[2,1-a]isoquinoline
  参考文献：
  名称：

  Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations

  摘要：

  The preparation of alicyclic ring-fused tetracyclic and pentacyclic benzimidazoles containing one and two fused aryl rings, respectively, is achieved conveniently in three steps, including Bu3SnH-mediated 6-exo-trig cyclization of sigma-aryl radicals generated from 1-allyl-2-(omega-bromoaryl)benzimidazoles. Inclusion Of 4,7-dimethoxy substituents on the radical precursors allows access to aryl ring-fused benzimidazolequitiones, a Unique family of potential bioreductive anti-cancer agents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.023

文献信息

• Synthesis of aryl ring-fused benzimidazolequinones using 6-exo-trig radical cyclizations
  作者：Eoin Moriarty、Fawaz Aldabbagh

  DOI：10.1016/j.tetlet.2009.07.023

  日期：2009.9

  The preparation of alicyclic ring-fused tetracyclic and pentacyclic benzimidazoles containing one and two fused aryl rings, respectively, is achieved conveniently in three steps, including Bu3SnH-mediated 6-exo-trig cyclization of sigma-aryl radicals generated from 1-allyl-2-(omega-bromoaryl)benzimidazoles. Inclusion Of 4,7-dimethoxy substituents on the radical precursors allows access to aryl ring-fused benzimidazolequitiones, a Unique family of potential bioreductive anti-cancer agents. (C) 2009 Elsevier Ltd. All rights reserved.