(R)-(+)-8,8a-dihydroindolizin-3(7H)-one | 378248-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (R)-(+)-8,8a-dihydroindolizin-3(7H)-one
• 英文别名: (R)-8,8A-dihydroindolizin-3(7H)-one；(8aR)-8,8a-dihydro-7H-indolizin-3-one
• CAS: 378248-22-7
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: MQMKHOKPJWNKJA-SSDOTTSWSA-N

物化性质

• 沸点：
  299.0±20.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (R)-(+)-8,8a-dihydroindolizin-3(7H)-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到(8aR)-1,7,8,8A-四氢-3(2H)-吲哚嗪酮
  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：

  3,4-dihydro-1(2H)-pyridinecarboxaldehyde 在 silver orthophosphate 、 Pd⁽⁰⁾-(R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl 、 苯基溴化镁 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-(+)-8,8a-dihydroindolizin-3(7H)-one
  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

文献信息

• 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.