((S)-1-Benzyl-3,3,3-trifluoro-2-oxo-propyl)-carbamic acid benzyl ester | 172097-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((S)-1-Benzyl-3,3,3-trifluoro-2-oxo-propyl)-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-4,4,4-trifluoro-3-oxo-1-phenylbutan-2-yl]carbamate
• CAS: 172097-18-6
• 化学式: C₁₈H₁₆F₃NO₃
• 分子量: 351.325
• InChiKey: YBQZBJPDLINRFK-HNNXBMFYSA-N

物化性质

• 沸点：
  456.7±45.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((S)-1-Benzyl-3,3,3-trifluoro-2-oxo-propyl)-carbamic acid benzyl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 氯甲酸乙酯 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.17h， 生成 [(S)-1-(1-Benzyl-3,3,3-trifluoro-2,2-dihydroxy-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Reaction of (Trifluoromethyl)trimethylsilane with Oxazolidin-5-ones:  Synthesis of Peptidic and Nonpeptidic Trifluoromethyl Ketones

  摘要：

  (Trifluoromethyl)trimethylsilane (TMS-CF3, the Ruppert Reagent) reacts with a variety of amino acid derived N-substituted oxazolidin-5-ones in excellent yields. Mild acid hydrolysis of adducts with electron-releasing substituents at C-2 affords N-substituted cx-amino trifluoromethyl ketones (TFMKs). N-CBZ-protected alpha-amino TFMKs are converted into hitherto unreported hydrochloride salts of alpha-amino TFMKs by hydrogenolysis. Coupling with aminoacid fluorides gives access to peptidic TFMKs which are of utility as protease inhibitors.

  DOI：

  10.1021/jo980443+
• 作为产物：
  描述：

  (4S)-N-benzyloxycarbonyl-2-(p-methoxyphenyl)-4-phenylmethyloxazolidin-5-one 在 Amberlite IR-120 、 四丁基氟化铵 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 ((S)-1-Benzyl-3,3,3-trifluoro-2-oxo-propyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Reaction of ruppert’s reagent (TMS-CF3) with Oxazolidinones: Synthesis of protected α-amino trifluoromethylketones

  摘要：

  (Trifluoromethyl)trimethylsilane adds to alpha-amino acid derived oxazolidin-5-ones in excellent yields. The adducts can be converted into protected alpha-amino trifluoromethylketones by acid hydrolysis.

  DOI：

  10.1016/0040-4039(95)01619-s

文献信息

• US6043278A
  申请人：——

  公开号：US6043278A

  公开（公告）日：2000-03-28
• Reaction of (Trifluoromethyl)trimethylsilane with Oxazolidin-5-ones:  Synthesis of Peptidic and Nonpeptidic Trifluoromethyl Ketones
  作者：Magnus W. Walter、Robert M. Adlington、Jack E. Baldwin、Christopher J. Schofield

  DOI：10.1021/jo980443+

  日期：1998.7.1

  (Trifluoromethyl)trimethylsilane (TMS-CF3, the Ruppert Reagent) reacts with a variety of amino acid derived N-substituted oxazolidin-5-ones in excellent yields. Mild acid hydrolysis of adducts with electron-releasing substituents at C-2 affords N-substituted cx-amino trifluoromethyl ketones (TFMKs). N-CBZ-protected alpha-amino TFMKs are converted into hitherto unreported hydrochloride salts of alpha-amino TFMKs by hydrogenolysis. Coupling with aminoacid fluorides gives access to peptidic TFMKs which are of utility as protease inhibitors.
• Reaction of ruppert’s reagent (TMS-CF3) with Oxazolidinones: Synthesis of protected α-amino trifluoromethylketones
  作者：Magnus W. Walter、Robert M. Adlington、Jack E. Baldwin、John Chuhan、Christopher J. Schofield

  DOI：10.1016/0040-4039(95)01619-s

  日期：1995.10

  (Trifluoromethyl)trimethylsilane adds to alpha-amino acid derived oxazolidin-5-ones in excellent yields. The adducts can be converted into protected alpha-amino trifluoromethylketones by acid hydrolysis.