4,4,4-trifluoro-3-methylbut-2-enamide camphor sultam | 1173178-24-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4,4,4-trifluoro-3-methylbut-2-enamide camphor sultam
• CAS: 1173178-24-9
• 化学式: C₁₅H₂₀F₃NO₃S
• 分子量: 351.39
• InChiKey: XQOBAXODLZJCOP-INEFNEAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4,4,4-trifluoro-3-methylbut-2-enamide camphor sultam 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 4,4,4-trifluoro-3-methylbutanamide camphor sultam 、 4,4,4-trifluoro-3-methylbutanamide camphor sultam
  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：

  (E)-4,4,4-trifluoro-3-methylbut-2-enoyl chloride 、 (2R)-bornane-10,2-sultam 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以43%的产率得到4,4,4-trifluoro-3-methylbut-2-enamide camphor sultam
  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