[5-Hydroxy-2-(4-methoxy-phenyl)-4,4-dimethyl-5-trifluoromethyl-oxazolidin-3-yl]-phenyl-methanone | 211619-65-7

• 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: [5-Hydroxy-2-(4-methoxy-phenyl)-4,4-dimethyl-5-trifluoromethyl-oxazolidin-3-yl]-phenyl-methanone
• 英文别名: [5-Hydroxy-2-(4-methoxyphenyl)-4,4-dimethyl-5-(trifluoromethyl)-1,3-oxazolidin-3-yl]-phenylmethanone
• CAS: 211619-65-7
• 化学式: C₂₀H₂₀F₃NO₄
• 分子量: 395.378
• InChiKey: RGHXBHRYTNEUKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [5-Hydroxy-2-(4-methoxy-phenyl)-4,4-dimethyl-5-trifluoromethyl-oxazolidin-3-yl]-phenyl-methanone 在 Amberlite IR-120 作用下， 以 乙腈 为溶剂， 生成 3-Amino-N-benzoyl-3-methyl-1,1,1-trifluorobutan-2-one 、 N-(3,3,3-Trifluoro-2,2-dihydroxy-1,1-dimethyl-propyl)-benzamide
  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：

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