(+)-trans-5-allylhexahydroindolizidin-3-one | 260964-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (+)-trans-5-allylhexahydroindolizidin-3-one
• 英文别名: (5R,8aR)-5-prop-2-enyl-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one
• CAS: 260964-77-0
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: QCRALXOOJFXAQQ-VHSXEESVSA-N

物化性质

• 沸点：
  291.8±7.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-trans-5-allylhexahydroindolizidin-3-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 trans-5-propylindolizidine
  参考文献：
  名称：

  Asymmetric Heck cyclization route to indolizidine and azaazulene alkaloids: synthesis of (+)-5-epiindolizidine 167B and indolizidine 223AB

  摘要：

  Asymmetric intramolecular Heck cyclization of endocyclic enamides occurs at room temperature to give indoloizidine and azaazulene ring systems in up to 86% enantiomeric excess. A synthesis of (+)-epiindolizidine 167B and formal synthesis of 5E,9Z-indolizidine 223AB is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01361-2
• 作为产物：
  描述：

  (5R)-5-(4,4-dimethoxybutyl)-1-[(4-methoxyphenyl)methyl]pyrrolidin-2-one 在 盐酸 、 camphor-10-sulfonic acid 、 氨 、 sodium 、 四氯化钛 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (+)-trans-5-allylhexahydroindolizidin-3-one
  参考文献：
  名称：

  Expedient synthesis of (+)-trans-5-allylhexahydroindolizidin-3-one

  摘要：

  Treatment of the bicyclic iminium ion derived from 5-methoxyhexahydroindolizidin-3-one with allyltrimethylsilane gave exclusively the diastereoisomer in which the allyl group was axial. This substrate is a useful precursor to 5-propyl-3-alkylindolizidine alkaloids. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02034-1

文献信息

• Stereoselective indolizidine synthesis: preparation of stereoisomers of gephyrotoxin-223AB
  作者：David J. Hart、Yeun Min Tsai

  DOI：10.1021/jo00144a003

  日期：1982.11
• Expedient synthesis of (+)-trans-5-allylhexahydroindolizidin-3-one
  作者：Deirdre Potts、Paul J Stevenson、Norris Thompson

  DOI：10.1016/s0040-4039(99)02034-1

  日期：2000.1

  Treatment of the bicyclic iminium ion derived from 5-methoxyhexahydroindolizidin-3-one with allyltrimethylsilane gave exclusively the diastereoisomer in which the allyl group was axial. This substrate is a useful precursor to 5-propyl-3-alkylindolizidine alkaloids. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Asymmetric Heck cyclization route to indolizidine and azaazulene alkaloids: synthesis of (+)-5-epiindolizidine 167B and indolizidine 223AB
  作者：Kurt Kiewel、Mathew Tallant、Gary A Sulikowski

  DOI：10.1016/s0040-4039(01)01361-2

  日期：2001.9

  Asymmetric intramolecular Heck cyclization of endocyclic enamides occurs at room temperature to give indoloizidine and azaazulene ring systems in up to 86% enantiomeric excess. A synthesis of (+)-epiindolizidine 167B and formal synthesis of 5E,9Z-indolizidine 223AB is described. (C) 2001 Elsevier Science Ltd. All rights reserved.