3-((2S,3R,4S)-4-butyl-3-propylpiperidin-2-yl)propan-1-ol | 1383291-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-((2S,3R,4S)-4-butyl-3-propylpiperidin-2-yl)propan-1-ol
• 英文别名: 3-[(2S,3R,4S)-4-butyl-3-propylpiperidin-2-yl]propan-1-ol
• CAS: 1383291-92-6
• 化学式: C₁₅H₃₁NO
• 分子量: 241.417
• InChiKey: DBICQNXWDSCTPF-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((2S,3R,4S)-4-butyl-3-propylpiperidin-2-yl)propan-1-ol 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以71%的产率得到(7S,8R,8aS)-7-butyl-8-propyloctahydroindolizine
  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
• 作为产物：
  描述：

  (2S,3R,4S)-3-allyl-1-benzyl-2-(3-(benzyloxy)propyl)-4-butylpiperidine 在 20 % Pd(OH)2/C 、 氢气 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以99%的产率得到3-((2S,3R,4S)-4-butyl-3-propylpiperidin-2-yl)propan-1-ol
  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