2-(1-benzyl-2-piperidinyl)-pyridine | 1061659-64-0

• 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: 2-(1-benzyl-2-piperidinyl)-pyridine
• 英文别名: 2-(1-benzylpiperidin-2-yl)pyridine；2-[1-(phenylmethyl)-2-piperidinyl]pyridine
• CAS: 1061659-64-0
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: ZGNGBBMEYSSAIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  2-(1-benzyl-2-piperidinyl)-pyridine 在 palladium hydroxide - carbon 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、405.33 kPa 条件下， 反应 48.0h， 以89%的产率得到2-哌啶-2-基吡啶双盐酸盐
  参考文献：
  名称：

  Chiral ligand 2-(2′-piperidinyl)pyridine: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes

  摘要：

  Chiral ligand 2-(2'-piperidinyl)pyridine 1 has been synthesized in good overall yield by sequential benzylation, hydrogenation and debenzylation of 2,2'-bipyridine. Its enantiomerically pure enantiomers have been obtained by resolution of 2-(1-benzyl-2-piperidinyl)pyridine 2 with D-tartaric acid (or L-tartaric acid) followed by debenzylation. The absolute configuration was determined by X-ray analysis of the (S)-2 D-tartrate. It was demonstrated that I can be used as an effective enantioselective catalyst in the addition of diethylzinc to aldehydes. Optically active secondary alcohols with up to 100% enantiomeric excess were obtained in high yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.005
• 作为产物：
  描述：

  1-benzyl-[2,2'-bipyridin]-1-ium bromide 在 platinum(IV) oxide 、 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 40.0 ℃ 、2.03 MPa 条件下， 反应 10.0h， 以76%的产率得到2-(1-benzyl-2-piperidinyl)-pyridine
  参考文献：
  名称：

  Enantioselective Henry Reaction Catalyzed by Cu^II Salt and Bipiperidine

  摘要：

  A complex derived from the enantiomeric bipiperidine and copper(II) acetate hydrate is an efficient catalyst for the enantioselective Henry reaction. The easy availability of both catalyst components, mild reaction conditions, high yield, and good to excellent enantioselectivity make the catalyst useful for everyday practice.

  DOI：

  10.1021/jo902664v

文献信息

• A New Sequential Intramolecular Cyclization Based on the Boekelheide Rearrangement
  作者：Assunta Massaro、Alessandro Mordini、Anna Mingardi、Jens Klein、Daniele Andreotti

  DOI：10.1002/ejoc.201000936

  日期：2011.1

  general and quite efficient method developed by using di-tert-butylsilyl bis(trifluoromethanesulfonate) as a new promoter for a Boekelheide-type reaction. The use of a new Boekelheide promoter, which is compatible with amino groups, opens new perspectives in view of its application in intramolecular cyclizations.

  吡咯烷和哌啶是由（氨基烷基）吡啶 N-氧化物合成的，采用一种通用且非常有效的方法，该方法使用二叔丁基甲硅烷基双（三氟甲磺酸酯）作为 Boekelheide 型反应的新促进剂。鉴于其在分子内环化中的应用，使用与氨基相容的新 Boekelheide 启动子开辟了新的前景。
• Enantioselective Henry Reaction Catalyzed by Cu^II Salt and Bipiperidine
  作者：Artur Noole、Kristin Lippur、Andrus Metsala、Margus Lopp、Tõnis Kanger

  DOI：10.1021/jo902664v

  日期：2010.2.19

  A complex derived from the enantiomeric bipiperidine and copper(II) acetate hydrate is an efficient catalyst for the enantioselective Henry reaction. The easy availability of both catalyst components, mild reaction conditions, high yield, and good to excellent enantioselectivity make the catalyst useful for everyday practice.
• Chiral ligand 2-(2′-piperidinyl)pyridine: synthesis, resolution and application in asymmetric diethylzinc addition to aldehydes
  作者：Yan-Qin Cheng、Zheng Bian、Chuan-Qing Kang、Hai-Quan Guo、Lian-Xun Gao

  DOI：10.1016/j.tetasy.2008.06.005

  日期：2008.7

  Chiral ligand 2-(2'-piperidinyl)pyridine 1 has been synthesized in good overall yield by sequential benzylation, hydrogenation and debenzylation of 2,2'-bipyridine. Its enantiomerically pure enantiomers have been obtained by resolution of 2-(1-benzyl-2-piperidinyl)pyridine 2 with D-tartaric acid (or L-tartaric acid) followed by debenzylation. The absolute configuration was determined by X-ray analysis of the (S)-2 D-tartrate. It was demonstrated that I can be used as an effective enantioselective catalyst in the addition of diethylzinc to aldehydes. Optically active secondary alcohols with up to 100% enantiomeric excess were obtained in high yields. (C) 2008 Elsevier Ltd. All rights reserved.