(R)-5-phenyl-3-((S)-1,1,1-trifluoropropan-2-yl)-5,6-dihydro-2H-1,4-oxazin-2-one | 1173178-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (R)-5-phenyl-3-((S)-1,1,1-trifluoropropan-2-yl)-5,6-dihydro-2H-1,4-oxazin-2-one
• 英文别名: (3R)-3-phenyl-5-[(2S)-1,1,1-trifluoropropan-2-yl]-2,3-dihydro-1,4-oxazin-6-one
• CAS: 1173178-11-4
• 化学式: C₁₃H₁₂F₃NO₂
• 分子量: 271.239
• InChiKey: LORPUMKQXDTJKK-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-5-phenyl-3-((S)-1,1,1-trifluoropropan-2-yl)-5,6-dihydro-2H-1,4-oxazin-2-one 在 platinum(IV) oxide 、 氢气 作用下， 以 三氟甲苯 为溶剂， 反应 1.5h， 生成 (3R,5R)-5-phenyl-3-((S)-1,1,1-trifluoropropan-2-yl)morpholin-2-one 、 (3S,5R)-5-phenyl-3-((S)-1,1,1-trifluoropropan-2-yl)morpholin-2-one
  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：

  (R)-4-phenyl-2-(-3,3,3-trifluoro-2-methylpropyl)-4,5-dihydrooxazole 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.83h， 生成 (R)-5-phenyl-3-((S)-1,1,1-trifluoropropan-2-yl)-5,6-dihydro-2H-1,4-oxazin-2-one 、 (R)-5-phenyl-3-((R)-1,1,1-trifluoropropan-2-yl)-5,6-dihydro-2H-1,4-oxazin-2-one 、 (R,Z)-5-phenyl-3-(1,1,1-trifluoropropan-2-ylidene)morpholin-2-one 、 (R,E)-5-phenyl-3-(1,1,1-trifluoropropan-2-ylidene)morpholin-2-one
  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