5-甲基-2-(4-(5-甲基-1H-苯并[d]咪唑-2-基)苯基)-1H-苯并[d]咪唑 | 308362-24-5

• 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: 5-甲基-2-(4-(5-甲基-1H-苯并[d]咪唑-2-基)苯基)-1H-苯并[d]咪唑
• 英文名称: 5-methyl-2-(4-(5-methyl-1H-benzo[d]imidazol-2-yl)phenyl)-1H-benzo[d]imidazole
• 英文别名: 6-methyl-2-[4-(6-methyl-1H-benzimidazol-2-yl)phenyl]-1H-benzimidazole
• CAS: 308362-24-5
• 化学式: C₂₂H₁₈N₄
• 分子量: 338.412
• InChiKey: GECUVJMEEJHNLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  57.4
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  对苯二甲醛 、 3,4-二氨基甲苯 在 双氧水 、 ferric nitrate 作用下， 反应 0.42h， 以93%的产率得到5-甲基-2-(4-(5-甲基-1H-苯并[d]咪唑-2-基)苯基)-1H-苯并[d]咪唑
  参考文献：
  名称：

  H2O2/Fe(NO3)3-Promoted Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles

  摘要：

  一种新的、便捷的2-取代苯并咪唑和苯并噻唑合成方法被介绍。该方法的主要优点包括：反应时间短，产物分离简便快捷，环境友好，化学选择性优异及产率出色。

  DOI：

  10.1055/s-0028-1087911

文献信息

• Mild and Highly Efficient Method for the Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles
  作者：Kiumars Bahrami、M. Mehdi Khodaei、Fardin Naali

  DOI：10.1021/jo8010232

  日期：2008.9.1

  A new, convenient method for the syntheses of 2-substituted benzimidazole and benzothizole is described. Short reaction times, large-scale synthesis, easy and quick isolation of the products, excellent chemoselectivity, and excellent yields are the main advantages of this procedure.

  描述了一种新的，方便的合成2-取代的苯并咪唑和苯并噻唑的方法。该方法的主要优点是反应时间短，大规模合成，产物的简便快速分离，优异的化学选择性和优异的收率。
• A Simple and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles
  作者：Kiumars Bahrami、Mohammad Khodaei、Iman Kavianinia

  DOI：10.1055/s-2007-965878

  日期：2007.2

  A simple and efficient procedure for the synthesis of substituted benzimidazoles through a one-pot condensation of o-phenylenediamines with aryl aldehydes in the presence of H2O2/HCl system in acetonitrile at room temperature is described. Short reaction time, large-scale synthesis, easy and quick isolation of the products, and excellent yields are the main advantages of this procedure.

  本文介绍了一种简单高效的一锅法合成取代苯并咪唑的工艺：在室温下，以乙腈为溶剂，在H2O2/HCl体系存在下，将邻苯二胺与芳醛进行缩合反应。该工艺的主要优点包括反应时间短、规模化合成、产物分离简便快捷以及产率优异。
• Synthetic Utility of Catalytic Fe(III)/Fe(II) Redox Cycling Towards Fused Heterocycles: A Facile Access to Substituted Benzimidazole, Bisbenzimidazole and Imidazopyridine Derivatives
  作者：Malvinder P. Singh、Sanjita Sasmal、Wei Lu、Manashi N. Chatterjee

  DOI：10.1055/s-2000-7111

  日期：——

  A catalytic Fe(III)/Fe(II) redox cycling approach has been examined and applied towards synthesis of a wide range of benzimidazole, bis-benzimidazole and imidazopyridine derivatives from oxidative coupling of aromatic ortho-diamines with aromatic as well as heterocyclic aldehydes bearing different types of substituents. This versatile and convenient method has further proven to be particularly useful

  已经研究了催化 Fe(III)/Fe(II) 氧化还原循环方法，并将其应用于通过芳香邻二胺与芳香醛和杂环醛的氧化偶联来合成各种苯并咪唑、双苯并咪唑和咪唑并吡啶衍生物不同类型的取代基。进一步证明，这种通用且方便的方法特别适用于迅速提供许多新型双苯并咪唑类 Hoechst 33 258 类似物，以作为荧光核酸结合探针的潜在开发。这里介绍了三十种不同化合物的成功制备和表征。
• PEG-mediated catalyst-free expeditious synthesis of 2-substituted benzimidazoles and bis-benzimidazoles under solvent-less conditions
  作者：Chhanda Mukhopadhyay、Pradip Kumar Tapaswi

  DOI：10.1016/j.tetlet.2008.08.041

  日期：2008.10

  A wide variety of 2-substituted benzimidazoles and bis-benzimidazoles were synthesized in high yields by PEG-mediated catalyst-free synthesis under solvent-less conditions. The products were directly recrystallized from hot methanol. The reaction occurred giving excellent yields with low as well as high molecular weight PEGs.

  在无溶剂条件下，通过PEG介导的无催化剂合成，可以高收率合成各种2-取代的苯并咪唑和双-苯并咪唑。产物从热甲醇中直接重结晶。发生反应后，无论是低分子量还是高分子量PEG，均具有出色的收率。
• One-pot synthesis of 2-substituted benzimidazoles catalyzed by anhydrous FePO4
  作者：Farahnaz K. Behbahani、Parisa Ziaei

  DOI：10.1007/s10593-012-1093-0

  日期：2012.10

  Anhydrous FePO4 has been employed as a catalyst for efficient synthesis of 2-substituted benzimidazoles. Simple and convenient procedure, easy purification and shorter reaction time are the advantages of this method, resulting in several known and three new compounds.