5,6-dimethyl-1-(4-methylbenzyl)-2-(4-methylphenyl)-1H-benzimidazole

• 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: 5,6-dimethyl-1-(4-methylbenzyl)-2-(4-methylphenyl)-1H-benzimidazole
• 英文别名: 5,6-dimethyl-1-(4-methylbenzyl)-2-(p-tolyl)-1H-benzo[d]imidazole；1-(4-methylbenzyl)-2-(4-methylphenyl)-5,6-dimethyl-1H-benzimidazole；5,6-dimethyl-2-(4-methylphenyl)-1-[(4-methylphenyl)methyl]benzimidazole
• 化学式: C₂₄H₂₄N₂
• 分子量: 340.468
• InChiKey: BOCQCDQCDDXGSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  对甲基苯甲醛 、 4，5-二甲基-1，2-苯二胺 在 三氟乙酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以90%的产率得到5,6-dimethyl-1-(4-methylbenzyl)-2-(4-methylphenyl)-1H-benzimidazole
  参考文献：
  名称：

  Trifluoroacetic Acid as an Efficient Catalyst for the Room Temperature Synthesis of 2-Aryl-1-arylmethyl-1H-1,3-benzimidazoles in Aqueous Media

  摘要：

  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。

  DOI：

  10.1155/2011/813796

文献信息

• 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。
• Selective Synthesis of 2-Substituted and 1,2-Disubstituted Benzimidazoles Directly from Aromatic Diamines and Alcohols Catalyzed by Molecularly Defined Nonphosphine Manganese(I) Complex
  作者：Kalicharan Das、Avijit Mondal、Dipankar Srimani

  DOI：10.1021/acs.joc.8b01316

  日期：2018.8.17

  Herein, we present a selective synthesis of 2-substituted and 1,2-disubstituted benzimidazoles by acceptorless dehydrogenative coupling of aromatic diamine with primary alcohols. The reaction is catalyzed by a phosphine-free tridentate NNS ligand-derived manganese(I) complex.

  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。
• PTSA-catalyzed selective synthesis and antibacterial evaluation of 1,2-disubstituted benzimidazoles
  作者：Jiaxu Fu、Yuandong Yue、Kejun Liu、Shuang Wang、Yiliang Zhang、Qing Su、Qiang Gu、Feng Lin、Yumin Zhang

  DOI：10.1007/s11030-022-10460-2

  日期：——

  Herein, we developed a convenient and efficient method via protonation of p-toluenesulfonic acid promoted cyclocondensation of o-phenylenediamine and aldehydes for selectively synthesizing 1,2-disubstituted benzimidazoles. This method displayed broad substrate adaptability and afforded the desired products in moderate to excellent yield in short reaction time. The effect of different substituents on

  在此，我们开发了一种通过对甲苯磺酸的质子化促进邻苯二胺和醛的环缩合来选择性合成 1,2-二取代苯并咪唑的简便有效的方法。该方法显示出广泛的底物适应性，并在较短的反应时间内以中等至优异的收率提供了所需的产物。通过扩展最佳反应条件考察了不同取代基对产率的影响，并通过理论计算进一步证实了这一点。这表明底物上氧原子和氮原子的表面静电势在1,2-二取代苯并咪唑的合成中起着重要作用。此外，化合物2t的晶体结构在正交空间群P2(1)/c中出现。此外，使用利福平作为阳性对照评估了抗耻垢分枝杆菌 (MC2155) 活性。产物(2a、2b、2c、2i、2j、2k、2m)表现出良好的抗菌活性，与利福平相当。 图形概要
• Eco-friendly synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using alumina-sulfuric acid as a heterogeneous reusable catalyst
  作者：Amit Pramanik、Rimi Roy、Sagar Khan、Avishek Ghatak、Sanjay Bhar

  DOI：10.1016/j.tetlet.2014.01.125

  日期：2014.3

  A cost-effective and eco-friendly synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles has been developed through the condensation of different aldehydes with o-phenylenediamine using alumina-sulfuric acid as a recyclable heterogeneous solid acid catalyst. Morphological properties of the catalyst have been investigated. Effect of different solvents and comparison of alumina-sulfuric acid with different acid catalysts have also been studied. A plausible mechanistic pathway has been proposed on the basis of the isotope labelling experiments where catalytic behaviour of alumina-sulfuric acid has been explained. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.