(αR,3R)-3-azido-N-(2-hydroxy-1-phenylethyl)piperidin-2-one | 178757-02-3

• 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: (αR,3R)-3-azido-N-(2-hydroxy-1-phenylethyl)piperidin-2-one
• CAS: 178757-02-3
• 化学式: C₁₃H₁₆N₄O₂
• 分子量: 260.296
• InChiKey: SIJAEIKEXJYNBX-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  89.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (αR,3R)-3-azido-N-(2-hydroxy-1-phenylethyl)piperidin-2-one 在 水 、 三苯基膦 作用下， 生成 (αR,3R)-3-amino-N-(2-hydroxy-1-phenylethyl)piperidin-2-one
  参考文献：
  名称：

  Conformationally restricted analogues of methionine: Synthesis of chiral 3-Amino-5-methylthio-2-piperidones

  摘要：

  (alpha R, 3RS, 5S)-3-amino-N-(2-hydroxy-1-phenylethyl)-5-methylthio-2-piperidones 1 have been synthesized from enamide 2 by subsequent free radical addition of methanothiol on position 5 and amination of 3-position. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4020(96)00340-7
• 作为产物：
  描述：

  5-溴戊酸甲酯 在 sodium azide 、 18-冠醚-6 、 溴 、 仲丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 50.42h， 生成 (αR,3R)-3-azido-N-(2-hydroxy-1-phenylethyl)piperidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis. XXXIX.1 Synthesis of 3-substituted piperidin-2-ones from chiral non-racemic lactams

  摘要：

  A series of 3-substituted piperidines in enantiomerically pure form has been synthesized from lactam 1 via the bromo derivative 2i. t-Butyl acetate and 5-methylpyridine derivatives 2g and 2h were obtained optically pure by direct alkylation of 1 with corresponding halides. Azido, amino or benzyloxy products were obtained by diastereoselective substitution of 2i. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4020(96)00339-0

文献信息

• Asymmetric synthesis. XXXIX.1 Synthesis of 3-substituted piperidin-2-ones from chiral non-racemic lactams
  作者：Laurent Micouin、Martine Bonin、Marie-Pierre Cherrier、Alain Mazurier、Alain Tomas、Jean-Charles Quirion、Henri-Philippe Husson

  DOI：10.1016/s0040-4020(96)00339-0

  日期：1996.5

  A series of 3-substituted piperidines in enantiomerically pure form has been synthesized from lactam 1 via the bromo derivative 2i. t-Butyl acetate and 5-methylpyridine derivatives 2g and 2h were obtained optically pure by direct alkylation of 1 with corresponding halides. Azido, amino or benzyloxy products were obtained by diastereoselective substitution of 2i. Copyright (C) 1996 Elsevier Science Ltd
• Conformationally restricted analogues of methionine: Synthesis of chiral 3-Amino-5-methylthio-2-piperidones
  作者：Ricardo Rodríguez、M. Angels Estiarte、Anna Diez、Mario Rubiralta、Anna Colell、Carmen García-Ruiz、JoséC. Fernández-Checa

  DOI：10.1016/s0040-4020(96)00340-7

  日期：1996.5

  (alpha R, 3RS, 5S)-3-amino-N-(2-hydroxy-1-phenylethyl)-5-methylthio-2-piperidones 1 have been synthesized from enamide 2 by subsequent free radical addition of methanothiol on position 5 and amination of 3-position. Copyright (C) 1996 Elsevier Science Ltd