1-ethyl-2-phenyl-4-styryl-5-p-tolyl-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: 1-ethyl-2-phenyl-4-styryl-5-p-tolyl-1H-imidazole
• 英文别名: 1-ethyl-5-(4-methylphenyl)-2-phenyl-4-[(E)-2-phenylethenyl]imidazole
• 化学式: C₂₆H₂₄N₂
• 分子量: 364.49
• InChiKey: KOHSBLPRTZDQDB-KNTRCKAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  苯甲酰氯 、 4-methyl-N-((1E,2E)-3-phenylallylidene)benzenesulfonamide 、 (E)-N-ethyl-1-(p-tolyl)methanimine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三(邻甲基苯基)磷 一氧化碳 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 45.0 ℃ 、413.68 kPa 条件下， 反应 18.0h， 以74%的产率得到1-ethyl-2-phenyl-4-styryl-5-p-tolyl-1H-imidazole
  参考文献：
  名称：

  A Direct, One Step Synthesis of Imidazoles from Imines and Acid Chlorides:  A Palladium Catalyzed Multicomponent Coupling Approach

  摘要：

  A palladium-catalyzed one-step synthesis of imidazoles from imines and acid chlorides is described. A plausible mechanism for this multicomponent reaction is provided, which explains the selective incorporation of two different imines into the final product with perfect regiocontrol. Overall, this catalytic process provides a modular method to prepare imidazoles directly from building blocks that are all either commercially available or readily generated.

  DOI：

  10.1021/ja060705m

文献信息

• A Direct, One Step Synthesis of Imidazoles from Imines and Acid Chlorides:  A Palladium Catalyzed Multicomponent Coupling Approach
  作者：Ali R. Siamaki、Bruce A. Arndtsen

  DOI：10.1021/ja060705m

  日期：2006.5.1

  A palladium-catalyzed one-step synthesis of imidazoles from imines and acid chlorides is described. A plausible mechanism for this multicomponent reaction is provided, which explains the selective incorporation of two different imines into the final product with perfect regiocontrol. Overall, this catalytic process provides a modular method to prepare imidazoles directly from building blocks that are all either commercially available or readily generated.