(S)-2-((S)-3-ethoxy-1,1,1-trifluoro-2-hydroxy-3-oxopropan-2-yl)-5-phenylpentanoic acid | 1594882-66-2

• 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)-2-((S)-3-ethoxy-1,1,1-trifluoro-2-hydroxy-3-oxopropan-2-yl)-5-phenylpentanoic acid
• CAS: 1594882-66-2
• 化学式: C₁₆H₁₉F₃O₅
• 分子量: 348.319
• InChiKey: SCYOFJPCPYZGMZ-DOMZBBRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (2S,3S)-4-benzyl 1-ethyl 2-hydroxy-3-((E)-3-phenylprop-1-en-1-yl)-2-(trifluoromethyl)succinate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以51 mg的产率得到(S)-2-((S)-3-ethoxy-1,1,1-trifluoro-2-hydroxy-3-oxopropan-2-yl)-5-phenylpentanoic acid
  参考文献：
  名称：

  Catalytic Asymmetric α-Aldol Reaction of Vinylogous N-Heterocyclic Carbene Enolates: Formation of Quaternary and Labile Tertiary Stereocenters

  摘要：

  Simple N-heterocyclic carbene (NHC)-enolates are widely studied versatile species. However, their vinylogous siblings (i.e., vinylogous NHC-enolates) have been much less studied. Here we disclose the first catalytic asymmetric a-aldol reaction of vinylogous NHC-enolates. With trifluoropyruvate as the carbon electrophile, the efficient C C bond formation process displays not only complete alpha-regioselectivity but also excellent stereocontrol over the two newly established challenging stereocenters (one quaternary and the other labile tertiary), furnishing a range of highly enantioenriched beta,gamma-unsaturated alpha-fluoroalkylated esters.

  DOI：

  10.1021/ol500830a