ethyl (2S)-2-hydroxy-2-(trifluoromethyl)butanoate

• 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 (2S)-2-hydroxy-2-(trifluoromethyl)butanoate
• 化学式: C₇H₁₁F₃O₃
• 分子量: 200.158
• InChiKey: DZSLKSOMGLWOLY-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  3,3,3-三氟丙酮酸乙酯 、 三乙基铝 在 (1R,2R)-2-(二甲基氨基)-1-苯基-1-丙醇 作用下， 以 乙醚 、 正己烷 为溶剂， 以95%的产率得到ethyl (2S)-2-hydroxy-2-(trifluoromethyl)butanoate
  参考文献：
  名称：

  A Practical Synthesis of 5-Lipoxygenase Inhibitor MK-0633

  摘要：

  Practical, chromatography-free syntheses of 5-lipoxygenase inhibitor MK-0633 p-toluenesullonate (1) are described. The first route used an asymmetric zincate addition to ethyl 2,2,2-trifluoropyruvate followed by 1,3,4-oxadiazole formation and reductive amination as key steps. An improved second route features an inexpensive diastereomeric salt resolution of vinyl hydroxy-acid 22 followed by a robust end-game featuring a through-process hydrazide acylation/1,3,4-oxadiazole ring closure/salt formation sequence to afford MK-0633 p-toluenesulfonate (1).

  DOI：

  10.1021/jo100561u

文献信息

• Asymmetric Organozincate Additions to Ethyl 2,2,2-Trifluoropyruvate
  作者：Francis Gosselin、Robert Britton、Jeffrey Mowat、Paul O’Shea、Ian Davies

  DOI：10.1055/s-2007-984911

  日期：——

  A chromatography-free synthesis of enantiomerically enriched chiral α-trifluoromethyl α-hydroxy acids prepared via an asymmetric ( R)-BINOL-mediated organozincate addition to ethyl 2,2,2-trifluoropyruvate ( 1) is reported.

  报道了通过不对称 (R)-BINOL 介导的有机锌酸盐加成到 2,2,2-三氟丙酮酸乙酯 (1) 制备的对映体富集的手性 α-三氟甲基 α-羟基酸的无色谱合成。
• A Practical Synthesis of 5-Lipoxygenase Inhibitor MK-0633
  作者：Francis Gosselin、Robert A. Britton、Ian W. Davies、Sarah J. Dolman、Danny Gauvreau、R. Scott Hoerrner、Gregory Hughes、Jacob Janey、Stephen Lau、Carmela Molinaro、Christian Nadeau、Paul D. O’Shea、Michael Palucki、Rick Sidler

  DOI：10.1021/jo100561u

  日期：2010.6.18

  Practical, chromatography-free syntheses of 5-lipoxygenase inhibitor MK-0633 p-toluenesullonate (1) are described. The first route used an asymmetric zincate addition to ethyl 2,2,2-trifluoropyruvate followed by 1,3,4-oxadiazole formation and reductive amination as key steps. An improved second route features an inexpensive diastereomeric salt resolution of vinyl hydroxy-acid 22 followed by a robust end-game featuring a through-process hydrazide acylation/1,3,4-oxadiazole ring closure/salt formation sequence to afford MK-0633 p-toluenesulfonate (1).