12b-methyl-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizine-3-carboxylic acid methyl ester | 60339-84-6

• 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: 12b-methyl-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizine-3-carboxylic acid methyl ester
• 英文别名: 5-methyl-8-carbomethoxy-1,2,6,7-tetrahydro-indolo[2,3-a]quinolizine；methyl 12b-methyl-2,6,7,12-tetrahydro-1H-indolo[2,3-a]quinolizine-3-carboxylate
• CAS: 60339-84-6
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: QOIYGBLOKHENOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12b-methyl-1,2,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizine-3-carboxylic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 溶剂黄146 为溶剂， 生成 (3R,12bS)-12b-Methyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine-3-carboxylic acid methyl ester 、 (3S,12bS)-12b-Methyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Model Studies on Interconversion of Roxburghine-Type Alkaloids. Acid-catalysed Epimerization of C-12b Substituted Indolo[2,3-a]quinolizidine Derivatives

  摘要：

  C-12b Methyl substituted indolo[2,3-a]quinolizidines possessing different structural features were prepared as model compounds to investigate whether different roxburghine alkaloids can be obtained by acid-catalysed epimerization. When they were subjected to epimerization under strongly acidic conditions (TFA), indoloquinolizidines (7) and (8) and lactams (12) and (13) epimerized as expected but the vinylogous urethanes (4) and (5) remained unaffected. The results indicate that the mechanism starting with protonation at the P-position of indole (Mechanism 1) is active in the acid-catalysed epimerization of vinylogous urethanes. This further suggests that roxburghine alkaloids do not epimerize at C-19.

  DOI：

  10.3987/com-98-8434