1-[5-Hydroxy-2-(4-methoxy-phenyl)-4,4-dimethyl-5-trifluoromethyl-oxazolidin-3-yl]-2-phenoxy-ethanone | 211619-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[5-Hydroxy-2-(4-methoxy-phenyl)-4,4-dimethyl-5-trifluoromethyl-oxazolidin-3-yl]-2-phenoxy-ethanone
• 英文别名: 1-[5-Hydroxy-2-(4-methoxyphenyl)-4,4-dimethyl-5-(trifluoromethyl)-1,3-oxazolidin-3-yl]-2-phenoxyethanone
• CAS: 211619-66-8
• 化学式: C₂₁H₂₂F₃NO₅
• 分子量: 425.405
• InChiKey: MQZJSPAQJWNREZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-[5-Hydroxy-2-(4-methoxy-phenyl)-4,4-dimethyl-5-trifluoromethyl-oxazolidin-3-yl]-2-phenoxy-ethanone 在 Amberlite IR-120 作用下， 以 乙腈 为溶剂， 生成 2-Phenoxy-N-(3,3,3-trifluoro-1,1-dimethyl-2-oxo-propyl)-acetamide 、 2-Phenoxy-N-(3,3,3-trifluoro-2,2-dihydroxy-1,1-dimethyl-propyl)-acetamide
  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：

  1-[2-(4-Methoxy-phenyl)-4,4-dimethyl-5-trifluoromethyl-5-trimethylsilanyloxy-oxazolidin-3-yl]-2-phenoxy-ethanone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 1-[5-Hydroxy-2-(4-methoxy-phenyl)-4,4-dimethyl-5-trifluoromethyl-oxazolidin-3-yl]-2-phenoxy-ethanone
  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+

文献信息

• 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.