1-benzyl-2-phenyl-1H-benzimidazole-5-carboxylic acid | 214903-47-6

• 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: 1-benzyl-2-phenyl-1H-benzimidazole-5-carboxylic acid
• 英文别名: 1-Benzyl-2-phenyl-1H-benzimidazol-5-carbonsaeure；1-Benzyl-2-phenylbenzimidazole-5-carboxylic acid
• CAS: 214903-47-6
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: HBXNPUFGCAHQBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-2-phenyl-1H-benzimidazole-5-carboxylic acid 在 氯化亚砜 作用下， 以 氯仿 、 苯 为溶剂， 反应 2.5h， 生成 (1-Benzyl-2-phenylbenzimidazol-5-yl)-(4-methylpiperazin-1-yl)methanone
  参考文献：
  名称：

  Synthesis of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity

  摘要：

  A series of 1,2-disubstituted benzimidazole-5(6)-carboxamides was prepared and evaluated in vitro for antimicrobial activity against Staphyloccus aureus, Escherichia coli and Candida albicans. The precursor benzimidazolecarboxylic acids 4a-c and 9a-c were prepared via oxidative condensation of diaminobenzoic acids with aldehydes and via several steps over the 2(1H)-benzimidazolones, respectively. All acids were converted to their acyl chlorides with SOCI2, then amidified with several N,N'-dialkylaminoethyl derivatives. Compounds 8a-c, 20 and 22 exhibited the best activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00045-7
• 作为产物：
  描述：

  methyl 4-(benzylamino)-3-nitrobenzoate 在 sodium hydroxide 、 水 、 copper diacetate 、 nickel dichloride 、 锌 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 6.0h， 生成 1-benzyl-2-phenyl-1H-benzimidazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity

  摘要：

  A series of 1,2-disubstituted benzimidazole-5(6)-carboxamides was prepared and evaluated in vitro for antimicrobial activity against Staphyloccus aureus, Escherichia coli and Candida albicans. The precursor benzimidazolecarboxylic acids 4a-c and 9a-c were prepared via oxidative condensation of diaminobenzoic acids with aldehydes and via several steps over the 2(1H)-benzimidazolones, respectively. All acids were converted to their acyl chlorides with SOCI2, then amidified with several N,N'-dialkylaminoethyl derivatives. Compounds 8a-c, 20 and 22 exhibited the best activity. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00045-7

文献信息

• ‘One-pot’ nitro reduction–cyclisation solid phase route to benzimidazoles
  作者：Zemin Wu、Philip Rea、Geoffrey Wickham

  DOI：10.1016/s0040-4039(00)01732-9

  日期：2000.12

  An improved solid phase synthesis of benzimidazoles is described. A polymer-bound o-nitroaniline was reacted with aldehydes in DMF in the presence of SnCl2·2H2O at 60°C for three hours to give benzimidazoles in excellent purity and good yield after TFA cleavage. A library of 25 benzimidazoles was prepared using this ‘one-pot’ procedure.

  描述了苯并咪唑的改进的固相合成。使聚合物结合的邻硝基苯胺在DMF中，在SnCl 2 ·2H 2 O的存在下，于60°C与醛反应3小时，从而在TFA裂解后以优异的纯度和良好的收率得到苯并咪唑。使用这种“一锅法”程序制备了25种苯并咪唑的文库。
• Ladenburg; Ruegheimer, Chemische Berichte, 1878, vol. 11, p. 1660
  作者：Ladenburg、Ruegheimer

  DOI：——

  日期：——
• Ladenburg, Chemische Berichte, 1878, vol. 11, p. 599
  作者：Ladenburg

  DOI：——

  日期：——
• Synthesis of some new benzimidazolecarboxamides and evaluation of their antimicrobial activity
  作者：Hakan Göker、Meral Tunçbilek、Gülgün Ayhan、Nurten Altanlar

  DOI：10.1016/s0014-827x(98)00045-7

  日期：1998.6

  A series of 1,2-disubstituted benzimidazole-5(6)-carboxamides was prepared and evaluated in vitro for antimicrobial activity against Staphyloccus aureus, Escherichia coli and Candida albicans. The precursor benzimidazolecarboxylic acids 4a-c and 9a-c were prepared via oxidative condensation of diaminobenzoic acids with aldehydes and via several steps over the 2(1H)-benzimidazolones, respectively. All acids were converted to their acyl chlorides with SOCI2, then amidified with several N,N'-dialkylaminoethyl derivatives. Compounds 8a-c, 20 and 22 exhibited the best activity. (C) 1998 Elsevier Science S.A. All rights reserved.