(Z)-3-(3-methyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile | 1541206-62-5

• 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-(3-methyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile
• 英文别名: (Z)-3-(3-methyl-2-sulfanylideneimidazol-1-yl)-3-phenylprop-2-enenitrile
• CAS: 1541206-62-5
• 化学式: C₁₃H₁₁N₃S
• 分子量: 241.316
• InChiKey: MJBDTECYMVCCAN-GHXNOFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基咪唑 、 3-苯基丙炔腈 在 sulfur 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以67%的产率得到(Z)-3-(3-methyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile
  参考文献：
  名称：

  Three-component reaction of imidazoles, cyanophenylacetylene, and chalcogens: stereoselective synthesis of 3-alkenyl-2-imidazolethiones and -selones

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.10.094

文献信息

• 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.