1-allyl-2-(2-bromophenyl)-1H-benzo[d]imidazole | 1187828-44-9

• 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: 1-allyl-2-(2-bromophenyl)-1H-benzo[d]imidazole
• 英文别名: 1-allyl-2-(2-bromophenyl)-1H-benzimidazole；2-(2-Bromophenyl)-1-prop-2-enylbenzimidazole；2-(2-bromophenyl)-1-prop-2-enylbenzimidazole
• CAS: 1187828-44-9
• 化学式: C₁₆H₁₃BrN₂
• 分子量: 313.197
• InChiKey: FMSQBOVTTHGZGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-allyl-2-(2-bromophenyl)-1H-benzo[d]imidazole 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium acetate 作用下， 以 2,4-滴二甲胺盐 为溶剂， 反应 2.0h， 以90%的产率得到5-methylbenzimidazo[2,1-a]isoquinoline
  参考文献：
  名称：

  Synthesis of substituted benzimidazo[2,1-a]isoquinolines and its condensed analogues using Pd(0)-catalyzed cyclization/C–H activation

  摘要：

  An efficient route for the synthesis of benzimidazo[2,1-a]isoquinolines and its condensed analogues has been developed via the palladium-catalyzed cyclization/C-H activation of N-allyl and N-methallyl derivatives of benzimidazoles. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.07.162
• 作为产物：
  描述：

  2-溴苯甲酸 在 sodium hydride 、 sodium hydrogensulfite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 1-allyl-2-(2-bromophenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Electrochemical synthesis of 5-trifluoroethyl dihydrobenzimidazo[2,1-a] isoquinolines from pendent unactivated alkenes via radical relay

  摘要：

  DOI：

  10.1016/j.tetlet.2023.154410

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.
• Metal-free synthesis of 5-alkylated dihydrobenzimidazo[2,1-a]isoquinolines from pendent unactivated alkenes via double C–H functionalizations
  作者：Mai Zhang、Xiao-Jing Tian、Yi-Han Gao、Ying Wen、Ting Xiao、Zhao-Yuan Yu、Jiang-Sheng Li、Zhi-Wei Li、Wei-Dong Liu

  DOI：10.1016/j.tet.2023.133510

  日期：2023.7
• Synthesis of substituted benzimidazo[2,1-a]isoquinolines and its condensed analogues using Pd(0)-catalyzed cyclization/C–H activation
  作者：Sukla Nandi、Shubhankar Samanta、Susovan Jana、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2010.07.162

  日期：2010.10

  An efficient route for the synthesis of benzimidazo[2,1-a]isoquinolines and its condensed analogues has been developed via the palladium-catalyzed cyclization/C-H activation of N-allyl and N-methallyl derivatives of benzimidazoles. (C) 2010 Elsevier Ltd. All rights reserved.
• Electrochemical synthesis of 5-trifluoroethyl dihydrobenzimidazo[2,1-a] isoquinolines from pendent unactivated alkenes via radical relay
  作者：Yi Lv、Jia-Ying Dai、Zi-Xin Zhao、Jia Liu、Zhi-Wei Li、Cui-Hong Lu、Yue-Fei Zhang、Wei-Dong Liu、Jiang-Sheng Li

  DOI：10.1016/j.tetlet.2023.154410

  日期：2023.4