(Z)-3-(1-phenyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile | 1079368-43-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (Z)-3-(1-phenyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile
• 英文别名: (Z)-1-phenyl-2-(2-cyano-1-phenylethenyl)imidazole；(Z)-3-phenyl-3-(1-phenylimidazol-2-yl)prop-2-enenitrile
• CAS: 1079368-43-6
• 化学式: C₁₈H₁₃N₃
• 分子量: 271.321
• InChiKey: CVBKVGPICSXTBB-BOPFTXTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苯基咪唑 、 3-苯基丙炔腈 反应 24.0h， 以59%的产率得到(Z)-3-(1-phenyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile
  参考文献：
  名称：

  Stereoselective C(2)-Vinylation of 1-Substituted Imidazoles with 3-Phenyl-2-propynenitrile

  摘要：

  First examples of direct vinylation of 1-substituted imidazoles at the 2-position of the imidazole nucleus are described. 1-Substituted imidazoles la-e are C(2)-vinylated with 3-phenyl-2-propynenitrile (2) at room temperature without catalyst and solvent to afford 3-(1-organyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitriles 3a-e, mainly (c.a. 95%) as (Z)-isomers, in 56-88% yield. The reaction is likely to involve the zwitterionic intermediates, which prototropically isomerizes to imidazole carbene and eventually undergoes the selective 3,2-shift of the functionalized vinyl substituent.

  DOI：

  10.1021/jo801240x

文献信息

• (Z)-1-Organyl-2-(2,4-dicyano-1,3-diphenyl-1,3-butadienyl)imidazoles from 1-substituted imidazoles with phenylcyanoacetylene
  作者：Boris A. Trofimov、Lyudmila V. Andriyankova、Kseniya V. Belyaeva、Anastasiya G. Mal’kina、Lina P. Nikitina、Andrei V. Afonin、Igor A. Ushakov

  DOI：10.1016/j.mencom.2009.01.017

  日期：2009.1

  1-Substituted imidazoles (R = Me, Et, Ph) react (20-25 degrees C) with phenylcyanoacetylene to afford the 1:2 adducts, (Z)-1-organyl2-(2,4-dicyano-1,3-diphenyl-1,3-butadienyl)imidazoles, in 10-20% yields, along with the 1:1 adducts, (Z)-1-organyl-2-(2-cyano-1-phenylethenyl)imidazoles.