(R)-2-(1-benzyl-2-piperidinyl)pyridine | 1061659-70-8

• 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: (R)-2-(1-benzyl-2-piperidinyl)pyridine
• 英文别名: (R)-2-(1-benzylpiperidin-2-yl)pyridine；2-[(2R)-1-benzylpiperidin-2-yl]pyridine
• CAS: 1061659-70-8
• 化学式: C₁₇H₂₀N₂
• 分子量: 252.359
• InChiKey: ZGNGBBMEYSSAIL-QGZVFWFLSA-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：

  (R)-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， 生成 2-(2R)-2-哌啶基吡啶
  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：

  2-(1-benzyl-2-piperidinyl)-pyridine 以71%的产率得到(R)-2-(1-benzyl-2-piperidinyl)pyridine
  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

文献信息

• 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.