ethyl 5-(4-chlorophenyl)-2-phenyl-1H-imidazole 4-carboxylate | 1199942-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-(4-chlorophenyl)-2-phenyl-1H-imidazole 4-carboxylate
• 英文别名: ethyl 5-(4-chlorophenyl)-2-phenyl-1H-imidazole-4-carboxylate；ethyl 5-(4-chlorophenyl)-2-phenylimidazole-4-carboxylate；ethyl 4-(4-chlorophenyl)-2-phenyl-1H-imidazole-5-carboxylate
• CAS: 1199942-24-9
• 化学式: C₁₈H₁₅ClN₂O₂
• 分子量: 326.782
• InChiKey: TZBMDKRYLPYCPR-UHFFFAOYSA-N

物化性质

• 沸点：
  556.2±40.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(苯基甲基)-肼羧酸 1,1-二甲基乙酯 、 ethyl 2-azido-3-(4-chlorophenyl)acrylate 以 乙腈 为溶剂， 反应 6.0h， 以84%的产率得到ethyl 5-(4-chlorophenyl)-2-phenyl-1H-imidazole 4-carboxylate
  参考文献：
  名称：

  Tuning the Annulation Reactivity of Vinyl Azides and Carbazates: A Divergent Synthesis of Aza-pyrimidinones and Imidazoles

  摘要：

  A divergent cascade annulation has been developed using readily available vinyl azides and carbazates with a wide range of substituents. Vinyl azides were successfully applied as bifunctional partners to prepare aza-pyrimidinones via 6-ring closure with carbazates as well as to construct polyfunctionalized imidazoles via 5-ring closure with N-substituted carbazates. The aza-heterocycles were obtained with high levels of chemoselectivity and excellent yields.

  DOI：

  10.1021/acs.orglett.5b02180

文献信息

• Carbene Reactivity of 4-Diazo-4<i>H</i>-imidazoles toward Nucleophiles and Aromatic Compounds
  作者：Matthew R. Smith、Alexander J. Blake、Christopher J. Hayes、Malcolm F. G. Stevens、Christopher J. Moody

  DOI：10.1021/jo902165w

  日期：2009.12.18

  Carbenes derived from diazoimidazolecarboxylates 4 under thermal or photochemical conditions undergo O−H and N−H insertion reactions with alcohols and amines, respectively, in moderate yield, in competition with reduction in good H-donor solvents. Dichloromethane reacts to give the corresponding 4-chloroimidazole. Aromatic hydrocarbons are excellent traps for the imidazolylidene carbene and lead to

  在热或光化学条件下，衍生自重氮咪唑羧酸盐4的羧化物分别以中等收率与醇和胺进行OH和NH插入反应，与减少良好的H供体溶剂竞争。二氯甲烷反应，得到相应的4-氯咪唑。芳族烃是咪唑基亚基卡宾的极佳捕集剂，并导致一系列芳基咪唑衍生物7。与吡啶的反应得到由咪唑基亚基卡宾形成的吡啶鎓内鎓盐8的第一个实例，而六氟苯中的辐射大概通过初始的正二十碳二烯中间体而得到了咪唑并偶氮碱11。