ethyl 5-(4-methylphenyl)-2-phenyl-1H-imidazole 4-carboxylate | 1199942-20-5

• 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-methylphenyl)-2-phenyl-1H-imidazole 4-carboxylate
• 英文别名: ethyl 2-phenyl-5-(p-tolyl)-1H-imidazole-4-carboxylate；ethyl 2-phenyl-5-(4-tolyl)imidazole-4-carboxylate；ethyl 4-(4-methylphenyl)-2-phenyl-1H-imidazole-5-carboxylate
• CAS: 1199942-20-5
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: MFLCPEDNPIBECG-UHFFFAOYSA-N

物化性质

• 沸点：
  540.8±38.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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-azido-3-(4-methylphenyl)propenoic acid ethyl ester 、 N-Boc-benzenecarboximidamide 以 乙腈 为溶剂， 反应 12.0h， 以78%的产率得到ethyl 5-(4-methylphenyl)-2-phenyl-1H-imidazole 4-carboxylate
  参考文献：
  名称：

  由乙烯基叠氮化物和idine与NHBoc作为离去基团合成多官能咪唑

  摘要：

  已经开发了一种由乙烯基叠氮化物和im合成多官能咪唑的有效方法。从叠氮化乙烯和am开始，这种转化无需任何添加剂即可进行，并且所得的咪唑可以用酯官能团修饰，该酯官能团是进一步修饰的有希望的部位。

  DOI：

  10.1016/j.tet.2019.04.008

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。
• Tuning the Annulation Reactivity of Vinyl Azides and Carbazates: A Divergent Synthesis of Aza-pyrimidinones and Imidazoles
  作者：Jiaan Shao、Xingyu Liu、Ke Shu、Pai Tang、Jing Luo、Wenteng Chen、Yongping Yu

  DOI：10.1021/acs.orglett.5b02180

  日期：2015.9.18

  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.
• Synthesis of polyfunctional imidazoles from vinyl azides and amidine along with NHBoc as a leaving group
  作者：Pai Tang、Di Ke、Jiaan Shao、Wenteng Chen、Yongping Yu

  DOI：10.1016/j.tet.2019.04.008

  日期：2019.8

  An efficient method for the synthesis of polyfunctional imidazoles from vinyl azides and amidine has been developed. Starting from vinyl azide and amidine, this transformation proceeds without any additives and the obtained imidazoles can be decorated with ester functional group that is a promising site for further modification.

  已经开发了一种由乙烯基叠氮化物和im合成多官能咪唑的有效方法。从叠氮化乙烯和am开始，这种转化无需任何添加剂即可进行，并且所得的咪唑可以用酯官能团修饰，该酯官能团是进一步修饰的有希望的部位。