trans-1-(2-hydroxyethyl)-2-(3-indolyl)-4-piperidone ethylene acetal | 136061-57-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: trans-1-(2-hydroxyethyl)-2-(3-indolyl)-4-piperidone ethylene acetal
• CAS: 136061-57-9
• 化学式: C₁₉H₂₆N₂O₃
• 分子量: 330.427
• InChiKey: YJHUETFOTXOOLJ-SJLPKXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  57.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-(苯磺酰)-3-吲哚甲醛 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 34.25h， 生成 trans-1-(2-hydroxyethyl)-2-(3-indolyl)-4-piperidone ethylene acetal
  参考文献：
  名称：

  Synthetic applications of protected 2-aryl-4-piperidones. 7. Synthesis of 1-ethylindolo[2,3-a]quinolizidin-2-one

  摘要：

  The synthesis of 1-ethylindolo[2,3-a]quinolizidin-2-one (1) by the intramolecular cyclization of protected N-(2-hydroxyethyl)-2-[1-(phenylsulfonyl)-3-indolyl]-4-piperidone 15 by the action of K(t)BuO and further acid treatment is reported. The methodology has been first carried out for its deethyl analogue 2 from (hydroxyethyl)piperidine 14 and has shown to be a good general method to reach indolo[2,3-a]quinolizidin-2-one systems. Compound 1 has also been obtained by an unusual rearrangement in acidic medium of 7-ethylhexahydropyrido[1',2':1,2]pyrazino[4,3-a]indole.

  DOI：

  10.1021/jo00022a015

文献信息

• Synthetic applications of protected 2-aryl-4-piperidones. 7. Synthesis of 1-ethylindolo[2,3-a]quinolizidin-2-one
  作者：Mario Rubiralta、Anna Diez、Cristina Vila、Yves Troin、Miguel Feliz

  DOI：10.1021/jo00022a015

  日期：1991.10

  The synthesis of 1-ethylindolo[2,3-a]quinolizidin-2-one (1) by the intramolecular cyclization of protected N-(2-hydroxyethyl)-2-[1-(phenylsulfonyl)-3-indolyl]-4-piperidone 15 by the action of K(t)BuO and further acid treatment is reported. The methodology has been first carried out for its deethyl analogue 2 from (hydroxyethyl)piperidine 14 and has shown to be a good general method to reach indolo[2,3-a]quinolizidin-2-one systems. Compound 1 has also been obtained by an unusual rearrangement in acidic medium of 7-ethylhexahydropyrido[1',2':1,2]pyrazino[4,3-a]indole.