2-benzyl-4-hydroxy-3-phenylisoxazolidin-5-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-benzyl-4-hydroxy-3-phenylisoxazolidin-5-one
• 英文别名: (3S,4S)-2-benzyl-4-hydroxy-3-phenyl-1,2-oxazolidin-5-one
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: UAEZICAWNWVCQI-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 二碳酸二叔丁酯 、 2-benzyl-4-hydroxy-3-phenylisoxazolidin-5-one 生成 甲基(2S,3S)-N-boc-3-苯基异丝氨酸盐酸
  参考文献：
  名称：

  Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N-Boc-phenylisoserine

  摘要：

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

  DOI：

  10.1021/jo971009v
• 作为产物：
  描述：

  [(1R,2S)-2-phenylcyclohexyl] 3-[benzyl-[tert-butyl(dimethyl)silyl]oxyamino]-3-phenyl-2-triethylsilyloxypropanoate 在 氢氟酸 作用下， 以 溶剂黄146 为溶剂， 以72%的产率得到2-benzyl-4-hydroxy-3-phenylisoxazolidin-5-one
  参考文献：
  名称：

  Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2S,3S)-N-Benzoyl- and N-Boc-phenylisoserine

  摘要：

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.

  DOI：

  10.1021/jo971009v

文献信息

• Regioselective ring opening of β-phenylglycidate and aziridine-2-carboxylates with N-alkylhydroxylamines: synthesis of isoxazolidinones
  作者：Mohamed Ali Tabarki、Rafâa Besbes

  DOI：10.1016/j.tet.2013.12.052

  日期：2014.2

  A simple and efficient method for the synthesis of 4-hydroxy or 4-alkylamino isoxazolidin-3-ones and 4-hydroxy isoxazolidin-5-ones is described: The synthesis involved the ring opening of ethyl beta-arylglycidates or ethyl N-alkylaziridine-2-carboxylates by free N-alkylhydroxylamines or hydroxylamine anions, followed by cyclization to give the title isoxazolidinones in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Totally Stereocontrolled Nitrone−Ketene Acetal Based Synthesis of (2<i>S</i>,3<i>S</i>)-<i>N</i>-Benzoyl- and <i>N</i>-Boc-phenylisoserine
  作者：Sylvie Jost、Yves Gimbert、Andrew E. Greene、Frédéric Fotiadu

  DOI：10.1021/jo971009v

  日期：1997.9.1

  A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N-benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.