5-methoxyhexahydroindolizidin-3-one | 260964-76-9

• 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: 5-methoxyhexahydroindolizidin-3-one
• 英文别名: (5S,8aR)-5-methoxy-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one
• CAS: 260964-76-9
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: IWXZVADAUUCDQV-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methoxyhexahydroindolizidin-3-one 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(+)-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
• 作为产物：
  描述：

  (S)-5-(hydroxymethyl)-1-(4-methoxyphenylmethyl)-2-pyrrolidinone 在 platinum(II) oxide 盐酸 、 camphor-10-sulfonic acid 、 氨 、 氢气 、 sodium 、 双(三甲基硅烷基)氨基钾 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 生成 5-methoxyhexahydroindolizidin-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

• Synthesis of (+)-piclavines A1 and A2
  作者：Helena McAlonan、Deirdre Potts、Paul J Stevenson、Norris Thompson

  DOI：10.1016/s0040-4039(00)00868-6

  日期：2000.7

  Piclavines A1 and A2 have been synthesised for the first time. The route is short with the key step being the reaction of a bicyclic N-acyl iminium ion with 3-trimethysilyl-1-decene. This convergent strategy gave exclusively compounds in which the pendant decenyl group was axial, as a 6:1 mixture of E:Z-alkene diastereoisomers. Reduction of the lactam carbonyl group gave a 6:1 mixture of piclavines A1 and

  Piclavines A1和A2首次合成。该路线很短，关键步骤是双环N-酰基亚胺鎓离子与3-三甲基甲硅烷基-1-癸烯的反应。这种收敛策略仅给出了其中的烯基侧链为轴向的化合物，为E：Z-烯烃非对映异构体的6：1混合物。内酰胺羰基的还原得到了苦瓜树A1和A​​2的6∶1混合物。
• 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.