2-Pyridin-4-yl-1-(pyridin-4-ylmethyl)benzimidazole | 1293398-05-6

• 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: 2-Pyridin-4-yl-1-(pyridin-4-ylmethyl)benzimidazole
• 英文别名: 2-pyridin-4-yl-1-(pyridin-4-ylmethyl)benzimidazole
• CAS: 1293398-05-6
• 化学式: C₁₈H₁₄N₄
• 分子量: 286.336
• InChiKey: VNZIOIJVGIWMMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-吡啶甲醛 、 邻苯二胺 在 polymeric resin-bound hexafluorophosphate ion 作用下， 以 甲醇 、 水 为溶剂， 反应 14.0h， 以82%的产率得到2-Pyridin-4-yl-1-(pyridin-4-ylmethyl)benzimidazole
  参考文献：
  名称：

  六氟磷酸钠结合的Amberlite树脂在水性介质中催化合成功能化的苯并咪唑和喹喔啉

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2012.09.045

文献信息

• Selectivity control during the solid supported protic acids catalysed synthesis of 1,2-disubstituted benzimidazoles and mechanistic insight to rationalize selectivity
  作者：Dinesh Kumar、Damodara N. Kommi、Rajesh Chebolu、Sanjeev K. Garg、Raj Kumar、Asit K. Chakraborti

  DOI：10.1039/c2ra21994h

  日期：——

  Selectivity control during the formation of 1,2-disubstituted benzimidazoles has been achieved for the reaction of o-phenylenediamine with aldehydes in the presence of solid supported protic acids as catalysts and choosing an appropriate reaction medium. Perchloric acid adsorbed on silica-gel (HClO4–SiO2) was found to be the most effective catalyst system for the synthesis of 1,2-disubstituted benzimidazoles in EtOH at rt. Apart from the catalyst and solvent, the electronic and steric factors of the aldehyde and the electronic factor of the o-phenylenediamine are also significant contributory factors in dictating the selectivity. An understanding of the mechanistic course of the formation of the 1,2-disubstituted benzimidazoles has been outlined that would rationalise the origin of selectivity control under the set experimental parameters.

  在形成1,2-二取代苯并咪唑的反应中，已经实现了选择性控制，该反应是对邻苯二胺与醛类在固态酸催化剂的存在下进行的，同时选择了合适的反应介质。研究发现，吸附在硅胶上的高氯酸（HClO4–SiO2）是合成1,2-二取代苯并咪唑在室温下使用乙醇的最有效催化体系。除了催化剂和溶剂之外，醛的电子和空间因素以及邻苯二胺的电子因素也是决定选择性的显著因素。对于1,2-二取代苯并咪唑的形成机制的理解也已被概述，这将有助于解释在设定实验参数下选择性控制的来源。
• Catalytic role of sodium dodecyl sulfate: Selective synthesis of 1, 2-disubstituted benzimidazoles in water
  作者：Pranab Ghosh、Amitava Mandal

  DOI：10.1016/j.catcom.2011.01.005

  日期：2011.3

  A simple and efficient procedure for the synthesis of 1, 2-disubstituted benzimidazoles has been developed by a one-pot reaction of o-phenylenediamine with both aromatic and aliphatic aldehydes in the presence of sodium dodecyl sulfate in aqueous medium at room temperature in open air without any organic solvent. The surfactant is recycled. A plausible mechanistic approach has also been suggested.

  在室温下，在水性介质中，在十二烷基硫酸钠存在下，邻苯二胺与芳族和脂族醛同时进行一锅反应，已开发出一种简单有效的合成1，2-二取代苯并咪唑的方法。没有任何有机溶剂。表面活性剂被回收。还提出了一种可行的机械方法。
• γ-Maghemite-silica nanocomposite: A green catalyst for diverse aromatic N-heterocycles
  作者：Pranab Ghosh、Amitava Mandal、Raju Subba

  DOI：10.1016/j.catcom.2013.06.026

  日期：2013.11

  gamma-Maghemite-silica nanocomposite has been applied as a green catalyst to synthesize variety of aromatic N-heterocycles under solvent free conditions. Characterization was done by modern analytical tools (UV, IR, AAS, DSC, EDXRF, powdered XRD, EPR, Mossbauer and TEM). Mild reaction conditions and recyclability have made the present protocol both environmentally and economically viable. (c) 2013 Elsevier B.V. All rights reserved.