cis-4-amino-1-N-benzyl-3-phenylpiperidine

• 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: cis-4-amino-1-N-benzyl-3-phenylpiperidine
• 英文别名: cis-1-Benzyl-3-phenyl-4-amino-piperidin；rac-4-amino-1-benzyl-3-phenylpiperidine；(3R,4S)-1-benzyl-3-phenylpiperidin-4-amine
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: LGSNQVMIVAHETM-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-4-amino-1-N-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-[(3R,4S)-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
• 作为产物：
  描述：

  (3R,4S)-(+)-4-amino-1-benzyl-3-phenylpiperidinium (S)-mandelate 在 sodium chloride 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 以100%的产率得到cis-4-amino-1-N-benzyl-3-phenylpiperidine
  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

• 4-Aminopiperidine derivatives
  申请人：Boehringer Markus

  公开号：US20060135561A1

  公开（公告）日：2006-06-22

  The present invention relates to compounds of the formula (I) wherein R 1 and R 2 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with DPP-IV, such as diabetes, non-insulin dependent diabetes mellitus and/or impaired glucose tolerance, obesity, and/or metabolic syndrome or β-cell protection.

  本发明涉及如下式（I）的化合物，其中R1和R2如描述和权利要求中所定义，并且其药学上可接受的盐。这些化合物可用于治疗和/或预防与DPP-IV相关的疾病，如糖尿病、非胰岛素依赖型糖尿病和/或糖耐量受损、肥胖和/或代谢综合征或β-细胞保护。
• 4-AMINOPIPERIDINE DERIVATIVES
  申请人：Boehringer Markus

  公开号：US20100087485A1

  公开（公告）日：2010-04-08

  The present invention relates to compounds of the formula (I) wherein R 1 and R 2 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with DPP-IV, such as diabetes, non-insulin dependent diabetes mellitus and/or impaired glucose tolerance, obesity, and/or metabolic syndrome or β-cell protection.

  本发明涉及式(I)的化合物，其中R1和R2如描述和要求中所定义，并且其药学上可接受的盐。这些化合物可用于治疗和/或预防与DPP-IV相关的疾病，例如糖尿病、非胰岛素依赖性糖尿病和/或糖耐量受损、肥胖症和/或代谢综合征或β细胞保护。
• US7683079B2
  申请人：——

  公开号：US7683079B2

  公开（公告）日：2010-03-23
• 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.