(S)-5,5,5-trifluoro-N-((R)-2-hydroxy-1-phenylethyl)-4-methylpentanamide | 1173178-42-1

• 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)-5,5,5-trifluoro-N-((R)-2-hydroxy-1-phenylethyl)-4-methylpentanamide
• 英文别名: (4S)-5,5,5-trifluoro-N-[(1R)-2-hydroxy-1-phenylethyl]-4-methylpentanamide
• CAS: 1173178-42-1
• 化学式: C₁₄H₁₈F₃NO₂
• 分子量: 289.298
• InChiKey: FDGUANDOXVPQIV-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-5,5,5-trifluoro-N-((R)-2-hydroxy-1-phenylethyl)-4-methylpentanamide 在 二乙胺基三氟化硫 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.45h， 生成 (R)-4-phenyl-2-((S)-4,4,4-trifluoro-3-methylbutyl)-4,5-dihydrooxazole
  参考文献：
  名称：

  Oxazoline−Oxazinone Oxidative Rearrangement. Divergent Syntheses of (2S,3S)-4,4,4-Trifluorovaline and (2S,4S)-5,5,5-Trifluoroleucine

  摘要：

  Stereoselective syntheses of the valuable fluorinated amino acids (2S,3S)-4,4,4-trifluorovaline and (2S,4S)-5,5,5-trifluoroleucine have been achieved starting from 4,4,4-trifluoro-3-methylbutanoic acid by using a conceptually simple transformation: conversion to a chiral oxazoline, SeO2-promoted oxidative rearrangement to the dihydro-2H-oxazinone, and face-selective hydrogenation of the C=N bond, followed by hydrogenolysis-hydrolysis. The transformation is limited by the tendency of the intermediate beta-trifluoromethyldihydrooxazinone to undergo imine-enamine isomerization. Both amino acids were obtained as configurationally pure hydrochloride salts identical in all respects with those in literature reports,

  DOI：

  10.1021/jo900654y
• 作为产物：
  描述：

  (S)-5,5,5-trifluoro-4-methylpentanoic acid 、 D-苯甘氨醇 在 HATU 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (S)-5,5,5-trifluoro-N-((R)-2-hydroxy-1-phenylethyl)-4-methylpentanamide
  参考文献：
  名称：

  Oxazoline−Oxazinone Oxidative Rearrangement. Divergent Syntheses of (2S,3S)-4,4,4-Trifluorovaline and (2S,4S)-5,5,5-Trifluoroleucine

  摘要：

  Stereoselective syntheses of the valuable fluorinated amino acids (2S,3S)-4,4,4-trifluorovaline and (2S,4S)-5,5,5-trifluoroleucine have been achieved starting from 4,4,4-trifluoro-3-methylbutanoic acid by using a conceptually simple transformation: conversion to a chiral oxazoline, SeO2-promoted oxidative rearrangement to the dihydro-2H-oxazinone, and face-selective hydrogenation of the C=N bond, followed by hydrogenolysis-hydrolysis. The transformation is limited by the tendency of the intermediate beta-trifluoromethyldihydrooxazinone to undergo imine-enamine isomerization. Both amino acids were obtained as configurationally pure hydrochloride salts identical in all respects with those in literature reports,

  DOI：

  10.1021/jo900654y

文献信息

• Oxazoline−Oxazinone Oxidative Rearrangement. Divergent Syntheses of (2<i>S</i>,3<i>S</i>)-4,4,4-Trifluorovaline and (2<i>S</i>,4<i>S</i>)-5,5,5-Trifluoroleucine
  作者：Julie A. Pigza、Tim Quach、Tadeusz F. Molinski

  DOI：10.1021/jo900654y

  日期：2009.8.7

  Stereoselective syntheses of the valuable fluorinated amino acids (2S,3S)-4,4,4-trifluorovaline and (2S,4S)-5,5,5-trifluoroleucine have been achieved starting from 4,4,4-trifluoro-3-methylbutanoic acid by using a conceptually simple transformation: conversion to a chiral oxazoline, SeO2-promoted oxidative rearrangement to the dihydro-2H-oxazinone, and face-selective hydrogenation of the C=N bond, followed by hydrogenolysis-hydrolysis. The transformation is limited by the tendency of the intermediate beta-trifluoromethyldihydrooxazinone to undergo imine-enamine isomerization. Both amino acids were obtained as configurationally pure hydrochloride salts identical in all respects with those in literature reports,