(Z)-3-(1-allyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile | 1079368-45-8

• 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-allyl-1H-imidazol-2-yl)-3-phenyl-2-propenenitrile
• 英文别名: (Z)-3-phenyl-3-(1-prop-2-enylimidazol-2-yl)prop-2-enenitrile
• CAS: 1079368-45-8
• 化学式: C₁₅H₁₃N₃
• 分子量: 235.288
• InChiKey: ACVXMHRGOALYEW-ZSOIEALJSA-N

物化性质

• 沸点：
  423.3±55.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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 、 N-烯丙基咪唑 反应 24.0h， 以58%的产率得到(Z)-3-(1-allyl-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。
• Three-component reaction of imidazoles, cyanophenylacetylene, and chalcogens: stereoselective synthesis of 3-alkenyl-2-imidazolethiones and -selones
  作者：Kseniya V. Belyaeva、Ludmila V. Andriyankova、Lina P. Nikitina、Anastasiya G. Mal'kina、Andrei V. Afonin、Igor' A. Ushakov、Irina Yu. Bagryanskaya、Boris A. Trofimov

  DOI：10.1016/j.tet.2013.10.094

  日期：2014.2

  The three-component reaction of 1-substituted imidazoles, cyanophenylacetylene, and elemental sulfur or selenium proceeds readily (for sulfur at room temperature without solvent, and for selenium in boiling MeCN) to stereoselectively afford 3-(Z)-cyanophenylethenyl-2-imidazolethiones or -selones in yields ranging 39-97% (for thiones) and 39-84% (for selones). In this reaction, tellurium is inactive both under the above conditions and upon heating (50-55 degrees C) in DMSO, instead, only the C(2)-vinylation of the imidazole ring in up to 98% yield takes place. The Z-stereoselectivity of the reaction is close to 100% (for sulfur) and reaches 91-99% (for selenium). The reaction involves the zwitterionic adduct of imidazoles with cyanophenylacetylene, which converts to the carbene via proton transfer (from the imidazole 2 position to the carbanionic site of the zwitterion) further reacting with chalcogens. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.