2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin-2-one | 71824-45-8

• 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: 2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin-2-one
• 英文别名: 3,4,7,12-tetrahydroindolo<2,3-a>quinolizin-2(6H)-one；3,4,7,12-Tetrahydroindolo<2,3a>gumolizin-2(6H)-on；3,4,7,12-tetrahydro-6H-indolo[2,3-a]quinolizin-2-one；3,4,7,12-Tetrahydroindolo[2,3-a]quinolizin-2(6H)-one；4,6,7,12-tetrahydro-3H-indolo[2,3-a]quinolizin-2-one
• CAS: 71824-45-8
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: BWTJECARKHNGLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin-2-one 在 4-二甲氨基吡啶 、 1,4-diazabicyclo[5.4.0]-7-undecene 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.67h， 生成 dimethyl 17-oxo-3,14,15,16-tetradehydroyohimban-1,16-dicarboxylate
  参考文献：
  名称：

  Total syntheses of yohimbe alkaloids, with stereoselection for the normal, allo, and 3-epiallo series, based on annelations of 4-methoxy-1,2-dihydropyridones

  摘要：

  N-[2-(1H-3-indolyl)ethyl]-2,3-dihydro-4-pyridone (31) was generated in two steps (77% yield) from tryptamine and N-methyl-4-piperidone methiodide. Its cyclization (90% yield) and oxidation (91% yield) provided the tetracyclic analogue 32. O-Methylation and Robinson-type annelation of these vinylogous lactams (the latter in form of its N(a)-carbamate) furnished the dienones 38 (64%) and 43 (90%). Further elaboration by cyclization and/or reduction reactions selectively provided the 15,16-didehydroyohimbinones 7 or 44. Their reductions then led to yohimbinone (52, 20% overall yield from tryptamine), alloyohimbinone (11, 19% overall yield), and 3-epi-alloyohimbinone (10, 23% overall yield), which led to yohimbine (3), beta-yohimbine (9), 3-epi-alloyohimbine (53), and 3-epi-17-epi-alloyohimbine (54).

  DOI：

  10.1021/jo00008a025
• 作为产物：
  描述：

  N-[2-(1H-吲哚-3-基)乙基]甲酰胺 在 盐酸 、 次氯酸叔丁酯 、 水 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 5.42h， 生成 2,3,4,6,7,12-hexahydroindolo[2,3-a]quinolizin-2-one
  参考文献：
  名称：

  Total syntheses of yohimbe alkaloids, with stereoselection for the normal, allo, and 3-epiallo series, based on annelations of 4-methoxy-1,2-dihydropyridones

  摘要：

  N-[2-(1H-3-indolyl)ethyl]-2,3-dihydro-4-pyridone (31) was generated in two steps (77% yield) from tryptamine and N-methyl-4-piperidone methiodide. Its cyclization (90% yield) and oxidation (91% yield) provided the tetracyclic analogue 32. O-Methylation and Robinson-type annelation of these vinylogous lactams (the latter in form of its N(a)-carbamate) furnished the dienones 38 (64%) and 43 (90%). Further elaboration by cyclization and/or reduction reactions selectively provided the 15,16-didehydroyohimbinones 7 or 44. Their reductions then led to yohimbinone (52, 20% overall yield from tryptamine), alloyohimbinone (11, 19% overall yield), and 3-epi-alloyohimbinone (10, 23% overall yield), which led to yohimbine (3), beta-yohimbine (9), 3-epi-alloyohimbine (53), and 3-epi-17-epi-alloyohimbine (54).

  DOI：

  10.1021/jo00008a025

文献信息

• A new route to heterocyclic compounds by the mercuric acetate oxidation of N-alkyl substituted 4-piperidones
  作者：Andrew C. Flick、Albert Padwa

  DOI：10.1016/j.tetlet.2008.07.109

  日期：2008.9

  N-Alkyl substituted 4-piperidones readily undergo oxidation in high yield upon reaction with mercuric acetate. Application of the oxidation to the synthesis of the skeletal framework of several alkaloids is described.

  N-烷基取代的4-哌啶酮在与乙酸汞反应后容易以高收率进行氧化。描述了将氧化应用于几种生物碱的骨架构架的合成。
• Manna, Ranjan K.; Jaisankar, P.; Giri, Venkatachalam S., Journal of Chemical Research, Miniprint, 1999, # 6, p. 1510 - 1519
  作者：Manna, Ranjan K.、Jaisankar, P.、Giri, Venkatachalam S.

  DOI：——

  日期：——
• BLASKO G.; HONTY K.; NOVAK L.; STANTAY C., ACTA CHIM. ACAD SCI. HUNG., 1979, 99, NO 1, 35-41
  作者：BLASKO G.、 HONTY K.、 NOVAK L.、 STANTAY C.

  DOI：——

  日期：——
• KUEHNE, MARTIN E.;MUTH, RANDY S., J. ORG. CHEM., 56,(1991) N, C. 2701-2412
  作者：KUEHNE, MARTIN E.、MUTH, RANDY S.

  DOI：——

  日期：——
• Total syntheses of yohimbe alkaloids, with stereoselection for the normal, allo, and 3-epiallo series, based on annelations of 4-methoxy-1,2-dihydropyridones
  作者：Martin E. Kuehne、Randy S. Muth

  DOI：10.1021/jo00008a025

  日期：1991.4

  N-[2-(1H-3-indolyl)ethyl]-2,3-dihydro-4-pyridone (31) was generated in two steps (77% yield) from tryptamine and N-methyl-4-piperidone methiodide. Its cyclization (90% yield) and oxidation (91% yield) provided the tetracyclic analogue 32. O-Methylation and Robinson-type annelation of these vinylogous lactams (the latter in form of its N(a)-carbamate) furnished the dienones 38 (64%) and 43 (90%). Further elaboration by cyclization and/or reduction reactions selectively provided the 15,16-didehydroyohimbinones 7 or 44. Their reductions then led to yohimbinone (52, 20% overall yield from tryptamine), alloyohimbinone (11, 19% overall yield), and 3-epi-alloyohimbinone (10, 23% overall yield), which led to yohimbine (3), beta-yohimbine (9), 3-epi-alloyohimbine (53), and 3-epi-17-epi-alloyohimbine (54).