(2RS,3SR,4RS)-3-allyl-1-benzyl-4-isopropyl-2-methylpiperidine

• 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: (2RS,3SR,4RS)-3-allyl-1-benzyl-4-isopropyl-2-methylpiperidine
• 英文别名: (2S,3R,4S)-1-benzyl-4-butyl-2-methyl-3-prop-2-enylpiperidine
• 化学式: C₂₀H₃₁N
• 分子量: 285.473
• InChiKey: SDJJNFDSNBVAGI-IHPCNDPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2-benzyl-3-methyl-2-azabicyclo[2.2.2]oct-7-en-6-yl)methanol 在 四甲基乙二胺 、 copper(l) cyanide 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.58h， 生成 (2RS,3SR,4RS)-3-allyl-1-benzyl-4-isopropyl-2-methylpiperidine
  参考文献：
  名称：

  Grob Fragmentation of 2-Azabicyclo[2.2.2]oct-7-ene: Tool for the Stereoselective Synthesis of Polysubstituted Piperidines

  摘要：

  The Grob fragmentation of azabicyclo[2.2.2]octene leads to a dihydropyridinium intermediate. This highly reactive species reacts with a variety of organocuprates and other soft nucleophiles in a regioselective manner, allowing for the rapid and stereoselective synthesis of 2,3,4-trisubstituted 1,2,3,4-tetrahydropyridines. The resulting products were either reduced in situ to the corresponding piperidine or used to achieve the stereoselective construction of various nitrogen heterocycles.

  DOI：

  10.1021/jo300690h

文献信息

• Grob Fragmentation of 2-Azabicyclo[2.2.2]oct-7-ene: Tool for the Stereoselective Synthesis of Polysubstituted Piperidines
  作者：Gérald Lemonnier、André B. Charette

  DOI：10.1021/jo300690h

  日期：2012.7.6

  The Grob fragmentation of azabicyclo[2.2.2]octene leads to a dihydropyridinium intermediate. This highly reactive species reacts with a variety of organocuprates and other soft nucleophiles in a regioselective manner, allowing for the rapid and stereoselective synthesis of 2,3,4-trisubstituted 1,2,3,4-tetrahydropyridines. The resulting products were either reduced in situ to the corresponding piperidine or used to achieve the stereoselective construction of various nitrogen heterocycles.