(-)-(2S,6S)-6-methyl-2-phenylpiperidin-4-one | 246042-17-1

• 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: (-)-(2S,6S)-6-methyl-2-phenylpiperidin-4-one
• 英文别名: (2S,6S)-2-methyl-6-phenylpiperidin-4-one
• CAS: 246042-17-1
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: LHWIOVMOEBZHCM-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(2S,6S)-6-methyl-2-phenylpiperidin-4-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以96%的产率得到(-)-(2S,4R,6S)-6-methyl-2-phenylpiperidin-4-ol
  参考文献：
  名称：

  A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines

  摘要：

  A highly diastereoselective intramolecular Mannich reaction involving enantiopure alpha-methylamine 7 and achiral aldehydes is employed to prepare enantiomerically pure 2,6-cis-disubstituted piperidines. This methodology provides an efficient and selective route to 2,6-cis-disubstituted piperidines, 2,6-cis-disubstituted 4-piperidones and 2,6-cis-disubstituted 4-piperidinols. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00226-8
• 作为产物：
  描述：

  (-)-(2S,6S)-1-aza-6-methyl-2-phenyl-1',3'-dioxaspiro<5.5>undecane 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 240.0h， 以90%的产率得到(-)-(2S,6S)-6-methyl-2-phenylpiperidin-4-one
  参考文献：
  名称：

  A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines

  摘要：

  A highly diastereoselective intramolecular Mannich reaction involving enantiopure alpha-methylamine 7 and achiral aldehydes is employed to prepare enantiomerically pure 2,6-cis-disubstituted piperidines. This methodology provides an efficient and selective route to 2,6-cis-disubstituted piperidines, 2,6-cis-disubstituted 4-piperidones and 2,6-cis-disubstituted 4-piperidinols. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00226-8

文献信息

• β-Amino Acids to Piperidinones by Petasis Methylenation and Acid-Induced Cyclization
  作者：Louis V. Adriaenssens、Richard C. Hartley

  DOI：10.1021/jo7019948

  日期：2007.12.1

  [GRAPHICS]Ester-imine derivatives of beta-amino acids were methylenated with dimethyltitanocene under microwave irradiation and the resulting enol ethers cyclized with Bronsted acid or triisopropylaluminium to give 2,6-syn-disubstituted piperidinones in good yield and diastereoselectivity. The method is analogous to the Petasis-Ferrier rearrangement of 1,3dioxan-4-ones to give tetrahydropyranones.
• A practical asymmetric synthesis of 2,6-cis-disubstituted piperidines
  作者：Stéphane Ciblat、Pascale Besse、Jean-Louis Canet、Yves Troin、Henri Veschambre、Jacques Gelas

  DOI：10.1016/s0957-4166(99)00226-8

  日期：1999.6

  A highly diastereoselective intramolecular Mannich reaction involving enantiopure alpha-methylamine 7 and achiral aldehydes is employed to prepare enantiomerically pure 2,6-cis-disubstituted piperidines. This methodology provides an efficient and selective route to 2,6-cis-disubstituted piperidines, 2,6-cis-disubstituted 4-piperidones and 2,6-cis-disubstituted 4-piperidinols. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.