ethyl (2Z)-2-(1-cyano-1-hydroxyethyl)-3-phenylacrylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (2Z)-2-(1-cyano-1-hydroxyethyl)-3-phenylacrylate
• 英文别名: ethyl (2Z)-2-benzylidene-3-cyano-3-hydroxybutanoate
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: WKYPUSFLKNFCDC-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙酮腈 、 苯丙炔酸乙酯 在 六甲基磷酰三胺 、 二异丁基氢化铝 作用下， 生成 ethyl (2Z)-2-(1-cyano-1-hydroxyethyl)-3-phenylacrylate
  参考文献：
  名称：

  Vinylalumination of activated carbonyl compounds

  摘要：

  [alpha-(Ethoxycarbonyl)vinyl]diisobutylaluminum and its beta-methyl and -phenyl analogs react with activated ketones, such as alpha-keto esters, alpha-acyl cyanides, and alpha-acetylenic ketones to provide the corresponding alpha-hydroxyalkenylated products in high yields; (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02504-0

文献信息

• Vinylalumination of activated carbonyl compounds
  作者：P.Veeraraghavan Ramachandran、M.Venkat Ram Reddy、Michael T. Rudd

  DOI：10.1016/s0040-4039(98)02504-0

  日期：1999.1

  [alpha-(Ethoxycarbonyl)vinyl]diisobutylaluminum and its beta-methyl and -phenyl analogs react with activated ketones, such as alpha-keto esters, alpha-acyl cyanides, and alpha-acetylenic ketones to provide the corresponding alpha-hydroxyalkenylated products in high yields; (C) 1999 Elsevier Science Ltd. All rights reserved.
• Vinylalumination for the Synthesis of Functionalized Allyl Alcohols, Vinylepoxides, and α-Alkylidene-β-hydroxy-γ-lactones
  作者：P. Veeraraghavan Ramachandran、Michael T. Rudd、Thomas E. Burghardt、M. Venkat Ram Reddy

  DOI：10.1021/jo034954u

  日期：2003.11.1

  A modified hydroalumination protocol for the preparation of [alpha-(ethoxycarbonyl)vinyl]diisobutyl-aluminum and its beta-methyl or -phenyl analogues was developed. These vinylaluminum reagents react with aldehydes and ketones to provide the corresponding functionalized allyl alcohols in good to excellent yields. Perfluoroalkyl and -aryl carbonyl compounds, alpha-keto esters, alpha-acyl cyanides, and alpha-acetylenic ketones provide the corresponding alpha-hydroxyalkenes in high yields. The allyl alcohol product ratios from the vinylalumination of unsymmetrical alpha-diketones with [alpha-(ethoxycarbonyl)vinyl] diisobutylaluminum and its beta-methyl or -phenyl analogues depend on the steric and electronic environments of the ketones as well as the reagents. The products from the vinylalumination of alpha-bromoaldehydes and -ketones were cyclized With K2CO3 or KF under nonaqueous conditions to provide functionalized vinylepoxides in high yields. Vinylaluminations of keto-protected pyruvaldehyde provided the products, which were converted to alpha-alkylidene-beta-hydroxy-gamma-lactones.