5-(4-chlorophenyl)-2-(2-nitrophenyl)-4-phenyl-1H-imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-chlorophenyl)-2-(2-nitrophenyl)-4-phenyl-1H-imidazole
• 化学式: C₂₁H₁₄ClN₃O₂
• 分子量: 375.814
• InChiKey: FGOIMVFSJPGQBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-氯-4-(苯基乙炔基)苯 、 邻硝基苯甲醇 在 碘 、 二甲基亚砜 、 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 26.0h， 以62%的产率得到5-(4-chlorophenyl)-2-(2-nitrophenyl)-4-phenyl-1H-imidazole
  参考文献：
  名称：

  Molecular iodine/DMSO mediated oxidation of internal alkynes and primary alcohols using a one-pot, two step approach towards 2,4,5-trisubstituted imidazoles: Substrate scope and mechanistic studies

  摘要：

  An efficient, eco-friendly and practical oxidation of internal alkynes and primary alcohols as key steps towards the synthesis of 2,4,5-trisubstituted imidazoles is reported. This green synthetic methodology employed an acid and metal-free molecular iodine/DMSO system, to afford a variety of substituted imidazoles in moderate to good yields, with a range of functionalities tolerated. Mechanistic studies revealed two distinct oxidation pathways, which ultimately form the diketone and aldehyde that serve as key intermediates in the multicomponent domino synthesis. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131028