(RS)-N-benzoyl-2-(4'-methoxyphenyl)-1,3-oxazolidin-5-one | 191980-66-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (RS)-N-benzoyl-2-(4'-methoxyphenyl)-1,3-oxazolidin-5-one
• 英文别名: (R/S)-N-Benzoyl-2-(4'-methoxyphenyl)-1,3-oxazolidin-5-one；3-benzoyl-2-(4-methoxyphenyl)-1,3-oxazolidin-5-one
• CAS: 191980-66-2
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: AFPFPBWUKCVIJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (RS)-N-benzoyl-2-(4'-methoxyphenyl)-1,3-oxazolidin-5-one 在 Amberlite IR-120 、 四丁基氟化铵 作用下， 以 乙腈 为溶剂， 生成 N-(3,3,3-trifluoro-2,2-dihydroxypropyl)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：

  4-甲氧基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (RS)-N-benzoyl-2-(4'-methoxyphenyl)-1,3-oxazolidin-5-one
  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

• Perfluoralkyl substituted metallo-beta-lactamase inhibitors
  申请人：Isis Innovation Limited

  公开号：US06043278A1

  公开（公告）日：2000-03-28

  The invention concerns perfluoro-lower-alkyl derivatives of amino acids. A new synthetic route is provided for preparing .alpha.-aminotrifluoromethylketones, by converting .alpha.-amino acids to oxazolidin-5-ones which are then reacted with Ruppert's Reagent. Fluorinated derivatives of amino acids and peptides are shown to have a new property of inhibiting or inactivating metallo-.beta.-lactamase enzymes, and are thus valuable components of antibacterial formulations. Certain of the trifluoromethyl derivatives of amino acids are new compounds per se.

  本发明涉及氨基酸的全氟较低烷基衍生物。提供了一种新的合成路线，用于制备α-氨基三氟甲基酮，通过将α-氨基酸转化为噁唑烷-5-酮，然后与鲁珀特试剂反应。显示氟化氨基酸和肽的衍生物具有抑制或失活金属β-内酰胺酶酶的新属性，因此是抗菌制剂中有价值的组分。某些氨基酸的三氟甲基衍生物是新的化合物本身。
• 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.