(E)-2-formyl-3-(4-nitrophenyl)prop-2-enenitrile | 1031210-29-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: (E)-2-formyl-3-(4-nitrophenyl)prop-2-enenitrile
• CAS: 1031210-29-3
• 化学式: C₁₀H₆N₂O₃
• 分子量: 202.169
• InChiKey: XLLLGKPSMLGTLV-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(hydroxy(4-nitrophenyl)methyl)acrylonitrile 在 sodium nitrate 作用下， 反应 2.0h， 以75%的产率得到(E)-2-formyl-3-(4-nitrophenyl)prop-2-enenitrile
  参考文献：
  名称：

  Ionic liquid [Hmim]HSO4-promoted one-pot oxidative conjugate addition of sulfur-centred nucleophiles to Baylis–Hillman adducts

  摘要：

  The first example of the one-pot oxidative conjugate addition of sulfur-centred nucleophiles to Baylis-Hillman adducts is reported. The reaction involves oxidation of Baylis-Hillman adducts with NaNO3 in the Bronsted acidic ionic liquid [Hmim]HSO4 to give [E]-alpha-cyanocinnamaldehydes followed by conjugate hydrothiocyanation/hydrosulfenylation with NH4SCN/PhSH to afford the corresponding beta-thiocyanato (or beta-phenylsulfenyl)-alpha-cyanohydrocinnamaldehydes diastereoselectively in 76-89% yields in a one-pot procedure. After isolation of the product, the ionic liquid [Hmim]HSO4 could be easily recycled for further use. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.016

文献信息

• Ionic liquid [Hmim]HSO4-promoted one-pot oxidative conjugate addition of sulfur-centred nucleophiles to Baylis–Hillman adducts
  作者：Lal Dhar S. Yadav、Vishnu P. Srivastava、Rajesh Patel

  DOI：10.1016/j.tetlet.2008.03.016

  日期：2008.5

  The first example of the one-pot oxidative conjugate addition of sulfur-centred nucleophiles to Baylis-Hillman adducts is reported. The reaction involves oxidation of Baylis-Hillman adducts with NaNO3 in the Bronsted acidic ionic liquid [Hmim]HSO4 to give [E]-alpha-cyanocinnamaldehydes followed by conjugate hydrothiocyanation/hydrosulfenylation with NH4SCN/PhSH to afford the corresponding beta-thiocyanato (or beta-phenylsulfenyl)-alpha-cyanohydrocinnamaldehydes diastereoselectively in 76-89% yields in a one-pot procedure. After isolation of the product, the ionic liquid [Hmim]HSO4 could be easily recycled for further use. (C) 2008 Elsevier Ltd. All rights reserved.