4,9-dihydro-3H-pyrido<3,4-b>indole monoperchlorate | 6502-84-7

• 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: 4,9-dihydro-3H-pyrido<3,4-b>indole monoperchlorate
• 英文别名: 4,9-dihydro-3H-β-carboline; perchlorate；4,9-Dihydro-3H-β-carbolin; Perchlorat；4,9-dihydro-3H-beta-carboline；4,9-dihydro-3H-pyrido[3,4-b]indole;perchloric acid
• CAS: 6502-84-7
• 化学式: C₁₁H₁₀N₂*ClHO₄
• 分子量: 270.672
• InChiKey: JHMDOFLXOBNLRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.98
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  99.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,9-dihydro-3H-pyrido<3,4-b>indole monoperchlorate 在 盐酸 、 4-二甲氨基吡啶 、 1,4-diazabicyclo[5.4.0]-7-undecene 、 次氯酸叔丁酯 、 水 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.09h， 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 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以85%的产率得到4,9-dihydro-3H-pyrido<3,4-b>indole monoperchlorate
  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

• Schoepf; Steuer, Justus Liebigs Annalen der Chemie, 1947, vol. 558, p. 124,132
  作者：Schoepf、Steuer

  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).