(Z)-3-(1-ethyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile | 1079368-40-3

• 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-ethyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile
• 英文别名: (Z)-1-ethyl-2-(2-cyano-1-phenylethenyl)imidazole；(Z)-3-(1-ethylimidazol-2-yl)-3-phenylprop-2-enenitrile
• CAS: 1079368-40-3
• 化学式: C₁₄H₁₃N₃
• 分子量: 223.277
• InChiKey: PAKKTEXUFCJPGP-JYRVWZFOSA-N

物化性质

• 沸点：
  413.6±55.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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-乙基咪唑 、 3-苯基丙炔腈 反应 20.0h， 以56%的产率得到(Z)-3-(1-ethyl-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

• Three-component reaction between imidazoles, isocyanates, and cyanophenylacetylene: a short-cut to N-(Z)-alkenylimidazole-2-carboxamides
  作者：Kseniya V. Belyaeva、Ludmila V. Andriyankova、Lina P. Nikitina、Anastasiya G. Mal’kina、Andrei V. Afonin、Boris A. Trofimov

  DOI：10.1016/j.tetlet.2012.10.049

  日期：2012.12

  1-Substituted imidazoles, isocyanates, and cyanophenylacetylene react under mild (rt), non-catalytic solvent-free conditions to give (Z)-(2-cyano-1-phenylethenyl)imidazole-2-carboxamides in up to 72% yields and with ca. 100% stereoselectivity. The reaction starts from the initial formation of zwitterion/carbene intermediates captured by the isocyanate as the electrophile followed by migration of the

  1-取代的咪唑，异氰酸酯和氰基苯基乙炔在温和（rt），无催化的无溶剂条件下反应，以最高72％的收率得到（Z）-（2-氰基-1-苯基乙烯基）咪唑-2-甲酰胺。与约。100％立体选择性。反应开始于两性离子/卡宾中间体的初步形成，该中间体被异氰酸酯捕获为亲电子试剂，然后烯基部分从N-3原子迁移至羧酰胺氮的阴离子中心。因此，该反应提供了容易获得新的官能化咪唑家族的途径。
• (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.
• 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.