N-[(3S,4R)-1-benzyl-3-phenylpiperidin-4-yl]-1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide | 1215036-22-8

• 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: N-[(3S,4R)-1-benzyl-3-phenylpiperidin-4-yl]-1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide
• CAS: 1215036-22-8
• 化学式: C₂₈H₃₆N₂O₃S
• 分子量: 480.671
• InChiKey: XSRSCEOHGRAWTK-PAHOUZJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3S,4R)-(+)-4-amino-1-benzyl-3-phenylpiperidine 、 右旋樟脑-10-磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-[(3S,4R)-1-benzyl-3-phenylpiperidin-4-yl]-1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide
  参考文献：
  名称：

  Synthesis, resolution and absolute configuration of 4-amino-3-phenylpiperidine

  摘要：

  Racemic cis-4-amino-1-benzyl-3-phenylpiperidine was prepared by reductive amination of the respective 4-piperidone via its oxime. The resolution of the racemate was accomplished by crystallization as the mandelate. The enantiomeric purity of this material was checked by NMR after derivatization to the corresponding camphorsulfonamide to be 97% ee. The absolute configuration of one enantiomer was confirmed by X-ray single crystal diffraction of the para-bromobenzenesulfonamide derivative. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.019

文献信息

• Synthesis, resolution and absolute configuration of 4-amino-3-phenylpiperidine
  作者：Heiko Schramm、Jens Christoffers

  DOI：10.1016/j.tetasy.2009.10.019

  日期：2009.12

  Racemic cis-4-amino-1-benzyl-3-phenylpiperidine was prepared by reductive amination of the respective 4-piperidone via its oxime. The resolution of the racemate was accomplished by crystallization as the mandelate. The enantiomeric purity of this material was checked by NMR after derivatization to the corresponding camphorsulfonamide to be 97% ee. The absolute configuration of one enantiomer was confirmed by X-ray single crystal diffraction of the para-bromobenzenesulfonamide derivative. (C) 2009 Elsevier Ltd. All rights reserved.