1-benzyl-3-(pyridin-2-yl)piperidine | 861907-77-9

• 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-benzyl-3-(pyridin-2-yl)piperidine
• 英文别名: 1-benzylisoanabasine；2-(1-Benzylpiperidin-3-yl)pyridine
• CAS: 861907-77-9
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: RNZXCSZUVOWBTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-(pyridin-2-yl)piperidine 在 氯甲酸苄酯 、 盐酸 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以76%的产率得到2-(3-哌啶基)吡啶
  参考文献：
  名称：

  The natural alkaloid isoanabasine: synthesis from 2,3′-bipyridine, efficient resolution with BINOL, and assignment of absolute configuration by Mosher’s method

  摘要：

  A highly efficient and practical resolution or racemic 1-benzyiisoanabasine, which was synthesized by reduction of the benzyl salt of 2,3'-bipyridine, has been achieved through molecular complexation with (R)-BINOL or (S)-BINOL to afford pure enantiomers (100% ee). The two enantiomers of the natural alkaloid isoanabasine have been obtained by debenzylation of the corresponding enantiomeric 1-benzylisoanabasine. Using Mosher's method by NMR techniques, the absolute configuration of (-)-isoanabasine has been assigned as the (R)-configuration for the first time. Moreover, an unexpected rotamer ratio of Mosher's amide was observed. The sYn-form of two rotamers of (R)-MTPA-(R)-isoanabasine was predominant over the anti-form. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.012
• 作为产物：
  描述：

  2,3'-联吡啶 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 20.0 ℃ 、1.01 MPa 条件下， 反应 4.0h， 生成 1-benzyl-3-(pyridin-2-yl)piperidine
  参考文献：
  名称：

  The natural alkaloid isoanabasine: synthesis from 2,3′-bipyridine, efficient resolution with BINOL, and assignment of absolute configuration by Mosher’s method

  摘要：

  A highly efficient and practical resolution or racemic 1-benzyiisoanabasine, which was synthesized by reduction of the benzyl salt of 2,3'-bipyridine, has been achieved through molecular complexation with (R)-BINOL or (S)-BINOL to afford pure enantiomers (100% ee). The two enantiomers of the natural alkaloid isoanabasine have been obtained by debenzylation of the corresponding enantiomeric 1-benzylisoanabasine. Using Mosher's method by NMR techniques, the absolute configuration of (-)-isoanabasine has been assigned as the (R)-configuration for the first time. Moreover, an unexpected rotamer ratio of Mosher's amide was observed. The sYn-form of two rotamers of (R)-MTPA-(R)-isoanabasine was predominant over the anti-form. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.012

文献信息

• Pyridyltetrahydropyridines and pyridylpiperidines and method of manufacturing them
  申请人：Kuwabara Hirokazu

  公开号：US20070093528A1

  公开（公告）日：2007-04-26

  The present invention provides pyridine derivatives useful as intermediates of drugs and agricultural chemicals, electrophotographic receptors, dyes and so on. More specifically, the invention relates to novel pyridyltetrahydropyridines and novel pyridylpiperidines, and further to a method of manufacturing pyridine derivatives through reaction between bipyridine derivatives and benzyl halide or benzyloxycarbonyl halide and subsequent reduction of the resultant reaction products with the aid of palladium catalysts, platinum catalysts, ruthenium catalysts or rhodium catalysts.

  本发明提供了吡啶衍生物，作为药物和农业化学品的中间体，电子照相感受器，染料等。更具体地，本发明涉及新型吡啶基四氢吡啶和新型吡啶基哌啶，以及通过双吡啶衍生物和苯甲醰或苄氧羰基卤化物反应，并在钯催化剂、铂催化剂、钌催化剂或铑催化剂的帮助下还原所得反应产物的吡啶衍生物制备方法。
• Pyridyltetrahydropyridines and Pyridylpiperidines, and Method of Manufacturing Them
  申请人：Kuwabara Hirokazu

  公开号：US20100029947A1

  公开（公告）日：2010-02-04

  The present invention provides pyridine derivatives useful as intermediates of drugs and agricultural chemicals, electrophotographic receptors, dyes and so on. More specifically, the invention relates to novel pyridyltetrahydropyridines and novel pyridylpiperidines, and further to a method of manufacturing pyridine derivatives through reaction between bipyridine derivatives and benzyl halide or benzyloxycarbonyl halide and subsequent reduction of the resultant reaction products with the aid of palladium catalysts, platinum catalysts, ruthenium catalysts or rhodium catalysts.

  本发明提供了吡啶衍生物，可用作药物和农业化学品，电子照相受体，染料等的中间体。更具体地说，本发明涉及新型吡啶基四氢吡啶和新型吡啶基哌啶，以及通过双吡啶衍生物和苯甲醰或苄氧羰基卤化物的反应制备吡啶衍生物的方法，并借助钯催化剂、铂催化剂、钌催化剂或铑催化剂还原所得反应产物的方法。
• US7632950B2
  申请人：——

  公开号：US7632950B2

  公开（公告）日：2009-12-15
• US8530662B2
  申请人：——

  公开号：US8530662B2

  公开（公告）日：2013-09-10
• The natural alkaloid isoanabasine: synthesis from 2,3′-bipyridine, efficient resolution with BINOL, and assignment of absolute configuration by Mosher’s method
  作者：Chuan-Qing Kang、Yan-Qin Cheng、Hai-Quan Guo、Xue-Peng Qiu、Lian-Xun Gao

  DOI：10.1016/j.tetasy.2005.05.012

  日期：2005.6

  A highly efficient and practical resolution or racemic 1-benzyiisoanabasine, which was synthesized by reduction of the benzyl salt of 2,3'-bipyridine, has been achieved through molecular complexation with (R)-BINOL or (S)-BINOL to afford pure enantiomers (100% ee). The two enantiomers of the natural alkaloid isoanabasine have been obtained by debenzylation of the corresponding enantiomeric 1-benzylisoanabasine. Using Mosher's method by NMR techniques, the absolute configuration of (-)-isoanabasine has been assigned as the (R)-configuration for the first time. Moreover, an unexpected rotamer ratio of Mosher's amide was observed. The sYn-form of two rotamers of (R)-MTPA-(R)-isoanabasine was predominant over the anti-form. (c) 2005 Elsevier Ltd. All rights reserved.