(S)-ethyl 3-hydroxy-5-oxo-3-(trifluoromethyl)hexanoate | 1353741-42-0

• 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: (S)-ethyl 3-hydroxy-5-oxo-3-(trifluoromethyl)hexanoate
• 英文别名: ethyl (3S)-3-hydroxy-5-oxo-3-(trifluoromethyl)hexanoate
• CAS: 1353741-42-0
• 化学式: C₉H₁₃F₃O₄
• 分子量: 242.195
• InChiKey: GYVOGHSOJUDSPH-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  三氟乙酰乙酸乙酯 、 丙酮 在 (S)-di-tert-butyl 2-{3-[(1S,2S)-1,2-diphenyl-2-[(S)-(pyrrolidine-2-carboxamido)]ethyl]thioureido}succinate 作用下， 以 甲苯 为溶剂， 反应 44.0h， 生成 (S)-ethyl 3-hydroxy-5-oxo-3-(trifluoromethyl)hexanoate 、 (R)-ethyl 3-hydroxy-5-oxo-3-(trifluoromethyl)hexanoate
  参考文献：
  名称：

  Construction of Tertiary Alcohols Bearing Perfluoroalkyl Chains Catalyzed by Prolinamide-Thioureas

  摘要：

  A systematic study to evaluate the ability of various organocatalysts to catalyze the aldol reaction between acetone and 2,2,2-trifluoromethyl-l-phenylethanone was undertaken. Benchmark organocatalysts failed to catalyze this reaction. However, a prolinamide-thiourea consisting of (S)-prolinamide, (1S,2S)-diphenylethylenediamine, and (S)-ditert butyl aspartate proved to be an efficient catalyst, providing tertiary alcohols as the products of the reaction between ketones and perfluoroalkyl ketones in high to quantitative yields and high enantioselectivities (up 81% ee) at a catalyst loading of 2 mol %.

  DOI：

  10.1021/jo2020104

文献信息

• Construction of Tertiary Alcohols Bearing Perfluoroalkyl Chains Catalyzed by Prolinamide-Thioureas
  作者：Christoforos G. Kokotos

  DOI：10.1021/jo2020104

  日期：2012.1.20

  A systematic study to evaluate the ability of various organocatalysts to catalyze the aldol reaction between acetone and 2,2,2-trifluoromethyl-l-phenylethanone was undertaken. Benchmark organocatalysts failed to catalyze this reaction. However, a prolinamide-thiourea consisting of (S)-prolinamide, (1S,2S)-diphenylethylenediamine, and (S)-ditert butyl aspartate proved to be an efficient catalyst, providing tertiary alcohols as the products of the reaction between ketones and perfluoroalkyl ketones in high to quantitative yields and high enantioselectivities (up 81% ee) at a catalyst loading of 2 mol %.