1-(4-chlorobenzyl)-2-(4-chlorophenyl)-5,6-dimethyl-1H-benzo-[d]imidazole

• 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-(4-chlorobenzyl)-2-(4-chlorophenyl)-5,6-dimethyl-1H-benzo-[d]imidazole
• 英文别名: 1-(4-chlorobenzyl)-2-(4-chlorophenyl)-5,6-dimethyl-1H-benzimidazole；2-(4-Chlorophenyl)-1-[(4-chlorophenyl)methyl]-5,6-dimethylbenzimidazole
• 化学式: C₂₂H₁₈Cl₂N₂
• 分子量: 381.304
• InChiKey: USHFSVHHDGPSDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  4，5-二甲基-1，2-苯二胺 、 4-氯苯甲醇 在 C₁₃H₁₆MnN₂O₃S⁽¹⁺⁾*Br^(1-) 、 potassium tert-butylate 作用下， 以 neat (no solvent) 为溶剂， 反应 20.0h， 以76%的产率得到1-(4-chlorobenzyl)-2-(4-chlorophenyl)-5,6-dimethyl-1H-benzo-[d]imidazole
  参考文献：
  名称：

  分子定义的非膦锰（I）配合物直接催化芳香二胺和醇选择性合成2-取代和1,2-二取代的苯并咪唑

  摘要：

  在这里，我们介绍了通过芳族二胺与伯醇的无受体脱氢偶联选择性合成2取代和1，2-二取代的苯并咪唑。该反应由不含膦的三齿NNS配体衍生的锰（I）配合物催化。

  DOI：

  10.1021/acs.joc.8b01316

文献信息

• Chitosan-supported Fe3O4 nanoparticles: a magnetically recyclable heterogeneous nanocatalyst for the syntheses of multifunctional benzimidazoles and benzodiazepines
  作者：Ali Maleki、Nakisa Ghamari、Maryam Kamalzare

  DOI：10.1039/c3ra47366j

  日期：——

  An environmentally benign and clean biopolymer-based heterogeneous nanocatalyst was prepared and its properties and morphology were characterized using scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX) and X-ray diffraction (XRD). Then, its catalytic activity was investigated in two important organic reactions. In these reactions, efficient and selective syntheses of 1,2-disubstituted benzimidazole and 1,5-benzodiazepine derivatives were carried out using 1,2-diamines and aldehydes or ketones in the presence of a catalytic amount of magnetically recoverable chitosan-supported iron oxide nanoparticles (Fe3O4/chitosan), as a biodegradable nanocomposite, in ethanol at ambient temperature in high yields. The Fe3O4/chitosan nanocatalyst can be recovered easily and reused without any significant loss of the catalytic activity.

  制备了一种环境友好且清洁的生物聚合物基异质纳米催化剂，并通过扫描电子显微镜（SEM）、能量色散X射线光谱（EDX）和X射线衍射（XRD）对其性质和形态进行了表征。随后，研究了其在两种重要有机反应中的催化活性。在这些反应中，使用1,2-二胺和醛或酮在催化量的可磁回收壳聚糖支持铁氧化物纳米颗粒（Fe3O4/壳聚糖）的存在下，在室温下的乙醇中高效且选择性地合成了1,2-取代的苯并咪唑和1,5-苯并二氮杂卓衍生物。Fe3O4/壳聚糖纳米催化剂可以轻松回收并重复使用，且没有显著的催化活性损失。
• Practical, Ecofriendly, and Chemoselective Method for the Synthesis of 2-Aryl-1-arylmethyl-1<i>H</i>-benzimidazoles Using Amberlite IR-120 as a Reusable Heterogeneous Catalyst in Aqueous Media
  作者：Saikat Das Sharma、Dilip Konwar

  DOI：10.1080/00397910802448440

  日期：2009.2.25

  environmentally benign method has been developed for the exclusive formation of biologically significant 2-aryl-1-arylmethyl-1H-benzimidazoles under the heterogeneous catalysis of Amberlite IR-120 in aqueous media in excellent yields. The catalyst is recyclable without loss of activity.

  摘要 开发了一种简单、高效且环境友好的方法，用于在水介质中 Amberlite IR-120 的多相催化下以优异的产率独家形成具有生物学意义的 2-芳基-1-芳基甲基-1H-苯并咪唑。该催化剂可回收而不会损失活性。
• Highly Efficient Chemoselective Synthesis of 2-Aryl-1-arylmethyl-1H-Benzimidazoles by Using TiCp2Cl2 Catalyst
  作者：Samiran Halder、Arup Datta

  DOI：10.13005/ojc/360623

  日期：2020.12.31

  One pot highly efficient chemoselective N-arylmethyl benzimidazole has been prepared by using catalyst TiCp2Cl2 in tetrahydrofuran solvent smoothly. This method is very much effective for the condensation between different aldehydes and various ortho-phenylenediamine to synthesize N-substituted benzimidazole. Clean reaction procedure, quick reaction, easy purification and high yield of the product are some advantages of this protocol. All the target molecules were identified by spectroscopic analysis and also verified melting points from literature value.

  使用催化剂TiCp2Cl2在四氢呋喃溶剂中，通过一锅高效的化学选择性N-芳基甲基苯并唑合成了一种新的方法。该方法非常适用于不同醛类和各种邻苯二胺之间的缩合反应，以合成N-取代苯并唑。这种方案具有反应过程干净、反应快速、易于纯化和产物收率高等优点。所有目标分子均通过光谱分析鉴定，并从文献值验证了熔点。
• Trifluoroacetic Acid as an Efficient Catalyst for the Room Temperature Synthesis of 2-Aryl-1-arylmethyl-1<i>H</i>-1,3-benzimidazoles in Aqueous Media
  作者：Mohammad R. Mohammadizadeh、S. Zeinakhatoun Taghavi

  DOI：10.1155/2011/813796

  日期：——

  Trifluoroacetic acid (TFA) is introduced as a commercially available, inexpensive and effective catalyst for the selective and eco-compatible synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazolesviacondensation reaction ofo-phenylenediamine derivatives and aromatic aldehydes in ethanol/water at room temperature.

  三氟乙酸（TFA）被引入作为一种商业上可获得，廉价且有效的催化剂，用于在室温下以乙醇/水为溶剂，通过间苯二胺衍生物和芳香醛的缩合反应，选择性和环保地合成2-芳基-1-芳基甲基-1H-1,3-苯并咪唑。
• Selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles in water at ambient temperature
  作者：Peyman Salehi、Minoo Dabiri、Mohammad Ali Zolfigol、Somayeh Otokesh、Mostafa Baghbanzadeh

  DOI：10.1016/j.tetlet.2006.02.049

  日期：2006.4

  A highly selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles from the reaction of o-phenylenediamines and aromatic aldehydes in the presence of silica sulfuric acid is reported. The reactions were performed in ethanol or water and the catalyst could be reused for several runs. (c) 2006 Elsevier Ltd. All rights reserved.