1,2,3,5,6,8a-hexahydro-8-methoxycarbonylindolizine | 154223-64-0

• 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: 1,2,3,5,6,8a-hexahydro-8-methoxycarbonylindolizine
• CAS: 154223-64-0
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: CIOBWXHIGDMESS-UHFFFAOYSA-N

物化性质

• 沸点：
  262.5±20.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,2,3,5,6,8a-hexahydro-8-methoxycarbonylindolizine 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以65%的产率得到(1,2,3,5,6,8a-hexahydroindolizin-8-yl)methanol
  参考文献：
  名称：

  Rearrangement of isoxazoline-5-spiro derivatives. Part 10. Regioselective nitrone cycloadditions to methoxycarbonylmethylenecyclopropane: Synthesis of precursors of (±)-Lupinine, (±)-Epilupinine and (±)-Elaeokanine A

  摘要：

  The cycloaddition of cyclic nitrones to methoxycarbonylmethylenecyclopropane (1) gives adducts having the methoxycarbonyl group on C4 of the isoxazolidine ring with high regioselectivity. The thermal rearrangement of the adducts gives quinolizidinone 6 and indolizidinones 8 bearing the methoxycarbonyl group selectively at C-1 and at C-8, respectively. The two compounds are intermediates for new formal syntheses of the alkaloids (+/-)-Lupinine and (+/-)-Epilupinine, and (+/-)-Elaeokanine A, respectively.

  DOI：

  10.1016/s0040-4020(01)80188-5
• 作为产物：
  描述：

  8-methoxycarbonyloctahydroindolizin-7-one 在 吡啶 、 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 1,2,3,5,6,8a-hexahydro-8-methoxycarbonylindolizine
  参考文献：
  名称：

  Rearrangement of isoxazoline-5-spiro derivatives. Part 10. Regioselective nitrone cycloadditions to methoxycarbonylmethylenecyclopropane: Synthesis of precursors of (±)-Lupinine, (±)-Epilupinine and (±)-Elaeokanine A

  摘要：

  The cycloaddition of cyclic nitrones to methoxycarbonylmethylenecyclopropane (1) gives adducts having the methoxycarbonyl group on C4 of the isoxazolidine ring with high regioselectivity. The thermal rearrangement of the adducts gives quinolizidinone 6 and indolizidinones 8 bearing the methoxycarbonyl group selectively at C-1 and at C-8, respectively. The two compounds are intermediates for new formal syntheses of the alkaloids (+/-)-Lupinine and (+/-)-Epilupinine, and (+/-)-Elaeokanine A, respectively.

  DOI：

  10.1016/s0040-4020(01)80188-5