(4S)-N-benzyloxycarbonyl-2-(p-methoxyphenyl)-4-phenylmethyloxazolidin-5-one | 291279-18-0

• 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: (4S)-N-benzyloxycarbonyl-2-(p-methoxyphenyl)-4-phenylmethyloxazolidin-5-one
• 英文别名: benzyl (4S)-4-benzyl-2-(4-methoxyphenyl)-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 291279-18-0
• 化学式: C₂₅H₂₃NO₅
• 分子量: 417.461
• InChiKey: BNUQVUBDBKNWPK-NQCNTLBGSA-N

物化性质

• 沸点：
  620.8±55.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-N-benzyloxycarbonyl-2-(p-methoxyphenyl)-4-phenylmethyloxazolidin-5-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (4S,5R)-4-Benzyl-5-hydroxy-2-(4-methoxy-phenyl)-5-trifluoromethyl-oxazolidine-3-carboxylic 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：

  L-苯丙氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (4S)-N-benzyloxycarbonyl-2-(p-methoxyphenyl)-4-phenylmethyloxazolidin-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

• Process for producing alpha-aminoketones
  申请人：AJINOMOTO CO., INC.

  公开号：US20020035288A1

  公开（公告）日：2002-03-21

  A process for producing &agr;-aminohalomethyl ketones or N-protected &agr;-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, &agr;-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.

  从指定的3-噁唑烷-5-酮衍生物通过5-卤甲基-5-羟基-3-噁唑烷衍生物制备α-氨基卤甲基酮或N-保护的α-氨基卤甲基酮的过程。通过这个过程，可以在工业规模上高效经济地获得α-氨基卤甲基酮及相关化合物。
• Process for producing &agr;-aminoketones
  申请人：Ajinomoto Co., Inc.

  公开号：US06570039B2

  公开（公告）日：2003-05-27

  A process for producing &agr;-aminohalomethyl ketones or N-protected &agr;-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, &agr;-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.

  通过从特定的3-噁唑烷-5-酮衍生物经由5-卤甲基-5-羟基-3-噁唑烷衍生物制备&agr;-氨基卤甲基酮或N-保护的&agr;-氨基卤甲基酮的方法。通过这个过程，可以在工业规模上高效、经济地获得&agr;-氨基卤甲基酮及其相关化合物。
• Process for producing α-aminoketones
  申请人：Onishi Tomoyuki

  公开号：US06906224B2

  公开（公告）日：2005-06-14

  A process for producing α-aminohalomethyl ketones or N-protected α-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, α-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.

  一种从指定的3-噁唑烷-5-酮衍生物通过5-卤甲基-5-羟基-3-噁唑烷衍生物制备α-氨基卤甲基酮或N-保护的α-氨基卤甲基酮的方法。通过这种方法，可以在工业规模上高效经济地获得α-氨基卤甲基酮及其相关化合物。
• 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.
• Practical synthesis of α-aminoalkyl-α′-chloromethylketone derivatives. Part 1: Chloromethylation of N-protected 3-oxazolidin-5-ones
  作者：Tomoyuki Onishi、Naoko Hirose、Takashi Nakano、Masakazu Nakazawa、Kunisuke Izawa

  DOI：10.1016/s0040-4039(01)01114-5

  日期：2001.8

  Reaction of N-protected 3-oxazolidin-5-ones with in situ-generated chloromethyllithium afforded N-protected 5-chloromethyl-5-hydroxy-3-oxazolidines without racemization. They were easily hydrolyzed to give alpha -aminoalkyl-alpha ' -chloromethylketone derivatives, which are useful intermediates for several protease inhibitors. (C) 2001 Elsevier Science Ltd. All rights reserved.