ethyl (2Z)-2-(2,2,2-trifluoro-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-(2,2,2-trifluoro-1-hydroxyethyl)-3-phenylacrylate
• 英文别名: ethyl (2Z)-2-benzylidene-4,4,4-trifluoro-3-hydroxybutanoate
• 化学式: C₁₃H₁₃F₃O₃
• 分子量: 274.24
• InChiKey: QSHFPIPUEHWKIM-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,2,2-三氟乙醛 、 苯丙炔酸乙酯 在 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到ethyl (2Z)-2-(2,2,2-trifluoro-1-hydroxyethyl)-3-phenylacrylate
  参考文献：
  名称：

  Vinylalumination for the Synthesis of Functionalized Allyl Alcohols, Vinylepoxides, and α-Alkylidene-β-hydroxy-γ-lactones

  摘要：

  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.

  DOI：

  10.1021/jo034954u

文献信息

• Ramachandran, P. Veeraraghavan; Reddy, M. Venkat Ram; Rudd, Michael T., Chemical Communications, 1999, # 19, p. 1979 - 1980
  作者：Ramachandran, P. Veeraraghavan、Reddy, M. Venkat Ram、Rudd, Michael T.

  DOI：——

  日期：——
• Vinylalumination of fluoro-carbonyl compounds
  作者：P. Veeraraghavan Ramachandran、M. Venkat Ram Reddy、Michael T. Rudd、Javier Read de Alaniz

  DOI：10.1016/s0040-4039(98)01974-1

  日期：1998.11

  Ethyl acrylate and acrylonitrile fail to undergo efficient Baylis-Hillman reaction with fluoral, but provide good yields of products with pentafluorobenzaldehyde. Alternately, unsubstituted and beta-substituted [alpha- (ethoxycarbonyl)vinyl]aluminum react with perfluoroalkyl and -aryl aldehydes and ketones to provide the alpha-hydroxyalkenylated fluoroorganic compounds in good to excellent yields. (C) 1998 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.