methyl 1,2,6,7,8,8a-hexahydro-2-<2-(1H-indol-3-yl)ethyl>-6-oxo-5-isoquinolinecarboxylate | 132672-75-4

• 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: methyl 1,2,6,7,8,8a-hexahydro-2-<2-(1H-indol-3-yl)ethyl>-6-oxo-5-isoquinolinecarboxylate
• 英文别名: methyl 2-[2-(1H-indol-3-yl)ethyl]-6-oxo-1,7,8,8a-tetrahydroisoquinoline-5-carboxylate
• CAS: 132672-75-4
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: MFGOCEMFMJREBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1,2,6,7,8,8a-hexahydro-2-<2-(1H-indol-3-yl)ethyl>-6-oxo-5-isoquinolinecarboxylate 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 硫酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 42.33h， 生成 育亨宾
  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：

  2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4(1H)-pyridinone 在 1,4-diazabicyclo[5.4.0]-7-undecene 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 methyl 1,2,6,7,8,8a-hexahydro-2-<2-(1H-indol-3-yl)ethyl>-6-oxo-5-isoquinolinecarboxylate
  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

• 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).