1-肉桂基-2-(E)-苯乙烯基-1H-苯并[d]咪唑 | 1053058-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-肉桂基-2-(E)-苯乙烯基-1H-苯并[d]咪唑
• 英文名称: 1-cinnamyl-2-(E)-styryl-1H-benzo[d]imidazole
• 英文别名: 2-[(E)-2-phenylethenyl]-1-[(2E)-3-phenylprop-2-en-1-yl]-1H-benzimidazole；2-[(E)-2-phenylethenyl]-1-[(E)-3-phenylprop-2-enyl]benzimidazole
• CAS: 1053058-94-8
• 化学式: C₂₄H₂₀N₂
• 分子量: 336.436
• InChiKey: FEHAXRBZQGMLEQ-CFYUHYMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  biscinamaldehyde-o-phenylenediamine 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 以88%的产率得到1-肉桂基-2-(E)-苯乙烯基-1H-苯并[d]咪唑
  参考文献：
  名称：

  Facile Synthesis of 1,2-Disubstituted Benzimidazoles Usingp-Toluenesulfonic Acid through Grinding Method

  摘要：

  An efficient synthetic method for the highly selective synthesis of pharmacologically active 1,2-disubstituted benzimidazole derivatives fromo-phenylenediamine and various aromatic aldehydes catalyzed byp-toluenesulfonic acid through grinding under solvent-free condition is described. The reaction requires the catalyst only during the conversion of intermediateN,N '-dibenzylidene-o-phenylenediamine into the desired product. The products were obtained within a short time with good yields by using only a mortar and pestle, which makes the proposed method convenient and cost-effective.

  DOI：

  10.1134/s1070428020090201

文献信息

• Synthesis of functionalized benzimidazoles and quinoxalines catalyzed by sodium hexafluorophosphate bound Amberlite resin in aqueous medium
  作者：Pranab Ghosh、Amitava Mandal

  DOI：10.1016/j.tetlet.2012.09.045

  日期：2012.11

  for the selective synthesis of 1,2-disubstituted benzimidazoles and quinoxalines in water–methanol (1:1) mixture with the aid of resin bound hexafluorophosphate ion as catalyst is reported. The method is also effective for the incorporation of quinoxaline nucleus at the A ring of pentacyclic triterpenoid, friedelin. A plausible mechanism for the formation of disubstituted benzimidazole has also been suggested

  报道了一种非常简单，环保和通用的方法，该方法可通过树脂结合的六氟磷酸根离子作为催化剂，在水-甲醇（1：1）混合物中选择性合成1,2-二取代的苯并咪唑和喹喔啉。该方法对于在五环三萜类化合物Friedelin的A环上引入喹喔啉核也是有效的。还已经提出了形成二取代的苯并咪唑的合理机理。
• Water mediated chemoselective synthesis of 1,2-disubstituted benzimidazoles using o-phenylenediamine and the extended synthesis of quinoxalines
  作者：Jie-Ping Wan、Shi-Feng Gan、Jian-Mei Wu、Yuanjiang Pan

  DOI：10.1039/b914286j

  日期：——

  By applying water as the reaction medium, the one-pot synthesis of 1,2-disubstituted benzimidazoles has been achieved in excellent efficiency and selectivity at room temperature viatrimethylsilyl chloride promoted reaction of o-phenylenediamine with aldehyde. This green catalyst system has also been successfully extended to the synthesis of quinoxalines via the reaction of o-phenylenediamine with α-bromoketone. Water displayed a specific functionality in mediating the selectivity, and remarkable advantages over organic solvents in terms of yields as well as in the work up procedure of the reactions.

  通过使用水作为反应介质，在室温条件下，通过三甲基氯硅烷促进邻苯二胺与醛的反应，以优异的效率和选择性实现了1,2-二取代苯并咪唑的一锅法合成。这种绿色催化体系也已成功扩展到通过邻苯二胺与α-溴代酮的反应合成喹噁啉。水在调节选择性方面表现出特定的功能，在产率和反应后处理程序方面比有机溶剂具有显著优势。
• Synthesis of 1,2-disubstitued benzimidazoles using SiO2/ZnCl2
  作者：Raquel G. Jacob、Luiz G. Dutra、Cátia S. Radatz、Samuel R. Mendes、Gelson Perin、Eder J. Lenardão

  DOI：10.1016/j.tetlet.2009.01.076

  日期：2009.4

  A general and easy method for the synthesis of several 1,2-disubstituted benzimidazoles using SiO2/ZnCl2 and solvent-free conditions is described, This efficient and improved method furnishes selectively and in good yields the corresponding 1,2-bis(organyl)-benzimidazoles starting from o-phenylenediamine and aromatic or aliphatic aldehydes. The catalytic system was re-Used up three times and the use of focused microwaves accelerates the reaction. (C) 2009 Elsevier Ltd. All rights reserved.