(3aR,8S,9aR,9bS)-2,2-dimethyl-3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizin-8-ol | 145388-58-5

• 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: (3aR,8S,9aR,9bS)-2,2-dimethyl-3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizin-8-ol
• CAS: 145388-58-5
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: MUIJLEBFONALDG-JLIMGVALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,8S,9aR,9bS)-2,2-dimethyl-3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizin-8-ol 在 acid 作用下， 生成 (1S,2R,7S,8aR)-1,2,7-trihydroxy-octahydroindolizine
  参考文献：
  名称：

  Synthesis of (−)-8-deoxy-7-hydroxy-swainsonine and (±)-6,8-dideoxy-castanospermine

  摘要：

  A total synthesis of (1S,2R,7S,8aR)-1,2,7-trihydroxyindolizidine 3 has been achieved in few steps from lactam 4. The dihydroxyderivative 14 has also been PrePared with the same general synthetic approach adapting a Michael addition and a thioamide-diazoketone cyclocondensation as key steps.

  DOI：

  10.1016/s0040-4039(00)79036-8
• 作为产物：
  描述：

  在 dirhodium tetraacetate lithium aluminium tetrahydride 、 Raney-Nickel W₂ 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 生成 (3aR,8S,9aR,9bS)-2,2-dimethyl-3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizin-8-ol
  参考文献：
  名称：

  Synthesis of (−)-8-deoxy-7-hydroxy-swainsonine and (±)-6,8-dideoxy-castanospermine

  摘要：

  A total synthesis of (1S,2R,7S,8aR)-1,2,7-trihydroxyindolizidine 3 has been achieved in few steps from lactam 4. The dihydroxyderivative 14 has also been PrePared with the same general synthetic approach adapting a Michael addition and a thioamide-diazoketone cyclocondensation as key steps.

  DOI：

  10.1016/s0040-4039(00)79036-8

文献信息

• Synthesis of (−)-8-deoxy-7-hydroxy-swainsonine and (±)-6,8-dideoxy-castanospermine
  作者：Michele Maggini、Maurizio Prato、Massimo Ranelli、Gianfranco Scorrano

  DOI：10.1016/s0040-4039(00)79036-8

  日期：1992.10

  A total synthesis of (1S,2R,7S,8aR)-1,2,7-trihydroxyindolizidine 3 has been achieved in few steps from lactam 4. The dihydroxyderivative 14 has also been PrePared with the same general synthetic approach adapting a Michael addition and a thioamide-diazoketone cyclocondensation as key steps.