1,3-bis(4-chlorobenzyl)-1H-benzo[d]imidazol-2(3H)-one | 587009-25-4

• 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: 1,3-bis(4-chlorobenzyl)-1H-benzo[d]imidazol-2(3H)-one
• 英文别名: 1,3-Bis[(4-chlorophenyl)methyl]benzimidazol-2-one
• CAS: 587009-25-4
• 化学式: C₂₁H₁₆Cl₂N₂O
• 分子量: 383.277
• InChiKey: IAOJADYVLISIHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氯甲基苯并咪唑 以 乙醇 、 乙腈 为溶剂， 反应 84.5h， 生成 1,3-bis(4-chlorobenzyl)-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  A unique one-pot reaction via CC cleavage from aminomethylene benzimidazoles to access benzimidazolones with wide potentiality

  摘要：

  A unique one-pot reaction via C-C cleavage from aminomethylene benzimidazoles with commercial halides to access novel benzimidazolones is reported for the first time. The previously unexploited transformation is able to perform smoothly in the presence of commercial potassium carbonate, while the stronger inorganic bases or organic amines as catalysts are not favorable to the transformation. Significant influential factors including base, temperature, solvent, water content, and molar ratio of substrates to this reaction are investigated, and possibly mechanistic consideration is also discussed. Some synthesized benzimidazolones were evaluated and exhibited better bioactivities against tested strains than clinical drugs chloromycin, norfloxacin, and fluconazole. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.113

文献信息

• A unique one-pot reaction via CC cleavage from aminomethylene benzimidazoles to access benzimidazolones with wide potentiality
  作者：Hui-Zhen Zhang、Sheng-Feng Cui、Sangaraiah Nagarajan、Syed Rasheed、Gui-Xin Cai、Cheng-He Zhou

  DOI：10.1016/j.tetlet.2014.05.113

  日期：2014.7

  A unique one-pot reaction via C-C cleavage from aminomethylene benzimidazoles with commercial halides to access novel benzimidazolones is reported for the first time. The previously unexploited transformation is able to perform smoothly in the presence of commercial potassium carbonate, while the stronger inorganic bases or organic amines as catalysts are not favorable to the transformation. Significant influential factors including base, temperature, solvent, water content, and molar ratio of substrates to this reaction are investigated, and possibly mechanistic consideration is also discussed. Some synthesized benzimidazolones were evaluated and exhibited better bioactivities against tested strains than clinical drugs chloromycin, norfloxacin, and fluconazole. (C) 2014 Elsevier Ltd. All rights reserved.