ethyl 2-[1-(bromomethyl)-2,2,2-trifluoro-1-hydroxyethyl]acrylate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-[1-(bromomethyl)-2,2,2-trifluoro-1-hydroxyethyl]acrylate
• 英文别名: Ethyl 3-(bromomethyl)-4,4,4-trifluoro-3-hydroxy-2-methylidenebutanoate
• 化学式: C₈H₁₀BrF₃O₃
• 分子量: 291.065
• InChiKey: ARPJSBMBSJTJJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-[1-(bromomethyl)-2,2,2-trifluoro-1-hydroxyethyl]acrylate 在 potassium fluoride 作用下， 以 丙酮 为溶剂， 以82%的产率得到ethyl 2-[2-(trifluoromethyl)oxiran-2-yl]acrylate
  参考文献：
  名称：

  A convenient synthesis of functionalized vinylepoxides

  摘要：

  Functionalized vinylepoxides were synthesized, in high yields, from alpha-bromoaldehydes and -ketones via vinylalumination, followed by cyclization with K2CO3 or KF under non-aqueous conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01642-1
• 作为产物：
  描述：

  3-溴-1,1,1-三氟丙酮 、 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， 反应 1.0h， 以60%的产率得到ethyl 2-[1-(bromomethyl)-2,2,2-trifluoro-1-hydroxyethyl]acrylate
  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

• A convenient synthesis of functionalized vinylepoxides
  作者：P.Veeraraghavan Ramachandran、Marek P Krzeminski

  DOI：10.1016/s0040-4039(99)01642-1

  日期：1999.11

  Functionalized vinylepoxides were synthesized, in high yields, from alpha-bromoaldehydes and -ketones via vinylalumination, followed by cyclization with K2CO3 or KF under non-aqueous conditions. (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.