trans-2,2-(ethylenedioxy)-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizidine | 130179-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: trans-2,2-(ethylenedioxy)-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizidine
• 英文别名: 2,2-(ethylenedioxy)-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine；trans-2,2-(ethylendioxy).1,2,3,4,6,7,12,12b-octahydro<2,3-a>quinolizine；trans-2,2-(ethylenedioxy)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizidine；spiro[1,3-dioxolane-2,2'-3,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine]
• CAS: 130179-28-1
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: BDFJNKYIDHWBIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-2,2-(ethylenedioxy)-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizidine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到3,4,6,7,12,12b-Hexahydro-1H-indolo[2,3-a]quinolizin-2-one
  参考文献：
  名称：

  Synthesis of Indolo [2, 3-a] Ouinolizidin-2-One

  摘要：

  Ketalization of 3-acetyl-1,2,6,7,12,12b-hexahydroindo-lo[2,3-a]quinolizin-2-one (2) with ethylene glycol followed by sodium borohydride reduction and acid hydrolysis gave indolo[2,3-a]quinolizidin-2-one (1) in very high overall yield.

  DOI：

  10.1080/00397919209409259
• 作为产物：
  描述：

  2',3',5',6',8',8a'-hexahydrodispiro[indole-3,1'-indolizine-7',2''-[1,3]dioxolane] 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.5h， 生成 trans-2,2-(ethylenedioxy)-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizidine
  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

• Studies on the synthesis of indolo[2,3-α]quinolizidin-2-ones. II
  作者：Mario Rubiralta、Anna Diez、Cristina Vila

  DOI：10.1016/s0040-4020(01)86779-x

  日期：——
• KLIOZE S. S.; EHRGOTT F. J. JR.; WILKER J. C.; WOODWARD D. L., J. MED. CHEM. 1979, 22, NO 12, 1497-1509
  作者：KLIOZE S. S.、 EHRGOTT F. J. JR.、 WILKER J. C.、 WOODWARD D. L.

  DOI：——

  日期：——
• 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.
• Synthesis of Indolo [2, 3-<u>a</u>] Ouinolizidin-2-One
  作者：Venkatachalam S. Giri、Parasuraman Jai Sankar

  DOI：10.1080/00397919209409259

  日期：1992.11

  Ketalization of 3-acetyl-1,2,6,7,12,12b-hexahydroindo-lo[2,3-a]quinolizin-2-one (2) with ethylene glycol followed by sodium borohydride reduction and acid hydrolysis gave indolo[2,3-a]quinolizidin-2-one (1) in very high overall yield.