(Z)-3-(1-amyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile | 1079368-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-(1-amyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile
• 英文别名: (Z)-3-(1-pentylimidazol-2-yl)-3-phenylprop-2-enenitrile
• CAS: 1079368-42-5
• 化学式: C₁₇H₁₉N₃
• 分子量: 265.358
• InChiKey: LYLLLKJADLEEAL-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  3-苯基丙炔腈 、 1-戊基咪唑 反应 24.0h， 以88%的产率得到(Z)-3-(1-amyl-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

• Stereoselective <i>C</i>(2)-Vinylation of 1-Substituted Imidazoles with 3-Phenyl-2-propynenitrile
  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：10.1021/jo801240x

  日期：2008.11.21

  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.