(1'R,3S)-3-bromo-1-(2-hydroxy-1-phenylethyl)piperidin-2-one | 178899-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1'R,3S)-3-bromo-1-(2-hydroxy-1-phenylethyl)piperidin-2-one
• 英文别名: (3S)-3-bromo-1-[(1R)-2-hydroxy-1-phenylethyl]piperidin-2-one
• CAS: 178899-97-3
• 化学式: C₁₃H₁₆BrNO₂
• 分子量: 298.18
• InChiKey: FYQBQYVRMOBJSV-RYUDHWBXSA-N

物化性质

• 熔点：
  129 °C
• 沸点：
  456.3±45.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1'R,3S)-3-bromo-1-(2-hydroxy-1-phenylethyl)piperidin-2-one 在 sodium azide 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以78%的产率得到(αR,3R)-3-azido-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 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 为溶剂， 反应 48.42h， 生成 (1'R,3S)-3-bromo-1-(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

• Diastereoselective arylation of enantiopure 3-bromopiperidin-2-one derived from (R)-(−)-2-phenylglycinol with organocuprate reagents
  作者：Oscar Romero、Alejandro Castro、Joel L. Terán、Dino Gnecco、María L. Orea、Ángel Mendoza、Marcos Flores、Luis F. Roa、Jorge R. Juárez

  DOI：10.1016/j.tetlet.2011.08.124

  日期：2011.11

  The diastereoselective substitution of 3-bromolactam derived from (R)-(-)-2-phenylglycinol with a variety of arylcuprate reagents is presented. The stereochemical outcome of the substitution reaction is discussed. The method provides an efficient and straightforward route to enantiopure 3-arylpiperidines. (C) 2011 Elsevier Ltd. All rights reserved.
• 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