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

• 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: benzo[4,5]imidazo[1,2-f]phenanthridine-6-carbonitrile
• 英文别名: 6-cyano-benzo[4,5]imidazo[1,2-f]phenanthridine；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-carbonitrile；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-carbonitrile
• 化学式: C₂₀H₁₁N₃
• 分子量: 293.327
• InChiKey: NICOJLSAIBVFKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(1H-苯并[d]咪唑-2-基)苯甲腈 、 1,2-二溴苯 在 四(三苯基膦)钯 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以68%的产率得到benzo[4,5]imidazo[1,2-f]phenanthridine-6-carbonitrile
  参考文献：
  名称：

  Palladium-catalyzed tandem N–H/C–H arylation: regioselective synthesis of N-heterocycle-fused phenanthridines as versatile blue-emitting luminophores

  摘要：

  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。

  DOI：

  10.1039/c3ob41760c

文献信息

• 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.
• 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。