1-methyl-2-[bis(4-methylphenyl)methyl]-1H-benzimidazole | 1277098-94-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-methyl-2-[bis(4-methylphenyl)methyl]-1H-benzimidazole
• 英文别名: 2-[Bis(4-methylphenyl)methyl]-1-methylbenzimidazole；2-[bis(4-methylphenyl)methyl]-1-methylbenzimidazole
• CAS: 1277098-94-8
• 化学式: C₂₃H₂₂N₂
• 分子量: 326.441
• InChiKey: LCHKZISNLMDWKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1,2-二甲基苯并咪唑 、 对氯甲苯 在 palladium diacetate 、 sodium t-butanolate 、 三环己基膦 作用下， 以 邻二甲苯 为溶剂， 反应 12.0h， 以93%的产率得到1-methyl-2-[bis(4-methylphenyl)methyl]-1H-benzimidazole
  参考文献：
  名称：

  Pd(0)-Catalyzed Diarylation of sp³C−H Bond in (2-Azaaryl)methanes

  摘要：

  A highly efficient and selective palladium-catalyzed diarylation of (2-azaaryl)methanes at the methyl group is described. Aryl chlorides proved reactive enough. A palladium eta(3)-azaallyl intermediate has been identified on the basis of DFT studies.

  DOI：

  10.1021/ol200345a

文献信息

• Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF₃SO₃H. NMR and DFT studies of dicationic electrophilic species
  作者：Dmitry S Ryabukhin、Alexey N Turdakov、Natalia S Soldatova、Mikhail O Kompanets、Alexander Yu Ivanov、Irina A Boyarskaya、Aleksander V Vasilyev

  DOI：10.3762/bjoc.15.191

  日期：——

  Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkylbenzimidazoles with arenes in the Brønsted superacid TfOH resulted in the formation of the corresponding Friedel–Crafts reaction products, 2-diarylmethyl and 2-arylmethyl-substituted benzimidazoles, in yields up to 90%. The reaction intermediates, protonated species derived from starting benzimidazoles in TfOH, were thoroughly studied by means

  2-羰基-和2-羟基（或甲氧基）烷基苯并咪唑与芳烃在布朗斯台德超强酸TfOH中反应，形成相应的弗里德尔-克来福特反应产物，2-二芳基甲基和2-芳基甲基取代的苯并咪唑，产率高达90%。通过 NMR 和 DFT 计算对反应中间体（源自 TfOH 中起始苯并咪唑的质子化物质）进行了深入研究，并讨论了合理的反应机理。
• Pd(0)-Catalyzed Diarylation of sp³C−H Bond in (2-Azaaryl)methanes
  作者：Guoyong Song、Yan Su、Xue Gong、Keli Han、Xingwei Li

  DOI：10.1021/ol200345a

  日期：2011.4.15

  A highly efficient and selective palladium-catalyzed diarylation of (2-azaaryl)methanes at the methyl group is described. Aryl chlorides proved reactive enough. A palladium eta(3)-azaallyl intermediate has been identified on the basis of DFT studies.