(6S,8R,9S)-6,8-diethylhexahydroindolizin-5(1H)-one | 1187565-38-3

• 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: (6S,8R,9S)-6,8-diethylhexahydroindolizin-5(1H)-one
• 英文别名: (6S,8R,8aS)-6,8-diethyl-2,3,6,7,8,8a-hexahydro-1H-indolizin-5-one
• CAS: 1187565-38-3
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: NMWSFJVAEWAART-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (6S,8R,9S)-6,8-diethylhexahydroindolizin-5(1H)-one 、 propyllithium 在 硼烷 、 三氟乙酸 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 为溶剂， 以65%的产率得到(5R,6S,8R,9S)-6,8-diethyl-5-propyloctahydroindolizine
  参考文献：
  名称：

  Asymmetric Total Synthesis of Alkaloids 223A and 6-epi-223A

  摘要：

  Concise and asymmetric total synthesis of the title compounds are described. The key ring system was constructed using an intramolecular Schmidt reaction on a norbornenone derivative, which was subsequently subjected to ring-opening metathesis followed by reduction. An unusual isomerization of the C-6 ethyl group afforded the desired stereochemistry of the natural product. The synthesis is readily adaptable to analogue production.

  DOI：

  10.1021/ol901645j
• 作为产物：
  描述：

  (6R,8S,9S)-6,8-divinylhexahydroindolizin-5(1H)-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以98%的产率得到(6S,8R,9S)-6,8-diethylhexahydroindolizin-5(1H)-one
  参考文献：
  名称：

  Asymmetric Total Synthesis of Alkaloids 223A and 6-epi-223A

  摘要：

  Concise and asymmetric total synthesis of the title compounds are described. The key ring system was constructed using an intramolecular Schmidt reaction on a norbornenone derivative, which was subsequently subjected to ring-opening metathesis followed by reduction. An unusual isomerization of the C-6 ethyl group afforded the desired stereochemistry of the natural product. The synthesis is readily adaptable to analogue production.

  DOI：

  10.1021/ol901645j

文献信息

• Asymmetric Total Synthesis of Alkaloids 223A and 6-<i>epi</i>-223A
  作者：Partha Ghosh、Weston R. Judd、Timothy Ribelin、Jeffrey Aubé

  DOI：10.1021/ol901645j

  日期：2009.9.17

  Concise and asymmetric total synthesis of the title compounds are described. The key ring system was constructed using an intramolecular Schmidt reaction on a norbornenone derivative, which was subsequently subjected to ring-opening metathesis followed by reduction. An unusual isomerization of the C-6 ethyl group afforded the desired stereochemistry of the natural product. The synthesis is readily adaptable to analogue production.