6-butyl-9,10-dimethylbenzo[4,5]imidazo[2,1-a]isoquinoline | 1174039-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-butyl-9,10-dimethylbenzo[4,5]imidazo[2,1-a]isoquinoline
• 英文别名: 6-n-butyl-9,10-dimethylbenzimidazo[2,1-a]isoquinoline；6-Butyl-9,10-dimethylbenzimidazolo[2,1-a]isoquinoline；6-butyl-9,10-dimethylbenzimidazolo[2,1-a]isoquinoline
• CAS: 1174039-92-9
• 化学式: C₂₁H₂₂N₂
• 分子量: 302.419
• InChiKey: NWAKJOIHRXQJGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 palladium diacetate 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以30 mg的产率得到6-butyl-9,10-dimethylbenzo[4,5]imidazo[2,1-a]isoquinoline
  参考文献：
  名称：

  Nucleophilic Addition of Benzimidazoles to Alkynyl Bromides/Palladium-Catalyzed Intramolecular C–H Vinylation: Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines

  摘要：

  An efficient "one-pot" route for the synthesis of benzo[4,5]imidazo[2,1-a] isoquinolines has been developed via nucleophilic addition of 2-aryl benzimidazoles to alkynyl bromides and subsequent palladium-catalyzed intramolecular C-H vinylation.

  DOI：

  10.1021/jo302471z

文献信息

• One-pot concise syntheses of benzimidazo[2,1-a]isoquinolines by a microwave-accelerated tandem process
  作者：Noriko Okamoto、Keisuke Sakurai、Minoru Ishikura、Kei Takeda、Reiko Yanada

  DOI：10.1016/j.tetlet.2009.04.126

  日期：2009.7

  Direct, efficient syntheses of the benzimidazo[2,1-a]isoquinoline ring system have been achieved with 2-bromoarylaldehydes, terminal alkynes, and 1,2-phenylenediamines by a microwave-accelerated tandem process in which a Sonogashira coupling, 5-endo cyclization, oxidative aromatization, and 6-endo cyclization can be performed in a single synthetic operation.

  直接的，所述苯并咪唑的合成效率[2,1-一个]异喹啉环系统已经通过微波加速的串联过程与2- bromoarylaldehydes，末端炔烃，和1,2-苯二胺实现，其中Sonogashira偶联，5-内切环化，芳构化氧化和6-内环化可以在单一的合成操作来执行。
• Nucleophilic Addition of Benzimidazoles to Alkynyl Bromides/Palladium-Catalyzed Intramolecular C–H Vinylation: Synthesis of Benzo[4,5]imidazo[2,1-<i>a</i>]isoquinolines
  作者：Jinsong Peng、Guoning Shang、Chunxia Chen、Zhongshuo Miao、Bin Li

  DOI：10.1021/jo302471z

  日期：2013.2.1

  An efficient "one-pot" route for the synthesis of benzo[4,5]imidazo[2,1-a] isoquinolines has been developed via nucleophilic addition of 2-aryl benzimidazoles to alkynyl bromides and subsequent palladium-catalyzed intramolecular C-H vinylation.