6-methoxy-benzo[4,5]imidazo[1,2-f]phenanthridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-methoxy-benzo[4,5]imidazo[1,2-f]phenanthridine
• 英文别名: 6-methoxybenzo[4,5]imidazo[1,2-f ]phenanthridine；6-methoxybenzo[4,5]imidazo[1,2-f]phenanthridine；5-Methoxy-14,21-diazapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(21),2(7),3,5,8,10,12,15,17,19-decaene；5-methoxy-14,21-diazapentacyclo[12.7.0.02,7.08,13.015,20]henicosa-1(21),2(7),3,5,8,10,12,15,17,19-decaene
• 化学式: C₂₀H₁₄N₂O
• 分子量: 298.344
• InChiKey: BELHAWKNEZXBDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2-chloro-phenyl)-2-(4-methoxy-phenyl)-1H-benzoimidazole 在 N,N-二甲基乙酰胺 、 palladium diacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 对二甲苯 为溶剂， 反应 16.0h， 生成 6-methoxy-benzo[4,5]imidazo[1,2-f]phenanthridine
  参考文献：
  名称：

  级联钯催化N-芳基化和分子内CH偶联一锅法合成苯并咪唑[1,2-f]菲啶

  摘要：

  已经开发了一种有效的方案，该方案使用顺序 N-芳基化和分子内 C-H 偶联以良好的产率构建唑稠合菲啶杂环衍生物。这种新方法允许从容易获得的苯并 [d] 咪唑和 1,2-二溴苯一锅合成多取代的复杂分子。

  DOI：

  10.1002/ejoc.201301147

文献信息

• Palladium-catalyzed tandem N–H/C–H arylation: regioselective synthesis of N-heterocycle-fused phenanthridines as versatile blue-emitting luminophores
  作者：Lipeng Yan、Dongbing Zhao、Jingbo Lan、Yangyang Cheng、Qiang Guo、Xiaoyu Li、Ningjie Wu、Jingsong You

  DOI：10.1039/c3ob41760c

  日期：——

  A general and highly regioselective synthetic protocol for structurally diverse N-heteroaryl-fused phenanthridines has been developed. Varieties of fluorescence molecules comprising imidazole-fused, benzoimidazole-fused, indole-fused and pyrrole-fused phenanthridines were obtained by this modular approach, some of which exhibit excellent blue-emitting performance, high quantum yields, long fluorescence lifetimes, interesting electrochemical properties, and thermal stabilities.

  已开发出一种通用且高度区域选择性的合成协议，用于合成结构多样的N-杂芳基融合荧光芳胺。采用这种模块化方法获得了多种荧光分子，包括咪唑融合、苯并咪唑融合、吲哚融合和吡咯融合的荧光芳胺，其中一些表现出优异的蓝光发射性能、高量子产率、长荧光寿命、有趣的电化学性质和热稳定性。
• Palladium(II)-Catalyzed Sequential C–H Arylation/Aerobic Oxidative C–H Amination: One-Pot Synthesis of Benzimidazole-Fused Phenanthridines from 2-Arylbenzimidazoles and Aryl Halides
  作者：Gongyuan Zhao、Chunxia Chen、Yixia Yue、Yanhan Yu、Jinsong Peng

  DOI：10.1021/jo502632b

  日期：2015.3.6

  Starting from 2-arylbenzimidazoles and aryl halides, an efficient palladium-based catalytic method for the synthesis of benzimidazole-fused phenanthridines has been developed. This reaction sequence comprises intermolecular C-H arylation and intramolecular aerobic oxidative C-H amination, involving the rupture of two C-H bonds, one C-X bond, and one N-H bond in one pot. The Pd-II-Pd-IV-Pd-II and Pd-II-Pd-0-Pd-II catalytic cycles work together under the reported conditions to generate phenanthridines with diverse substituents.