1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(6S,12bS)-6-carboxymethyl-quinolizine | 139259-20-4

• 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: 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(6S,12bS)-6-carboxymethyl-quinolizine
• 英文别名: 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo[2,3-a]-(6S,12bS)-6-carboxymethyl-quinolizine；methyl (6S,12bS)-2-oxo-3,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine-6-carboxylate
• CAS: 139259-20-4；139345-60-1
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: JRHWVTWKVYVTJU-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tribenzyl 3,3',3''-((1,3,5-triazinane-1,3,5-triyl)tris(3-methoxy-3-oxopropane-2,1-diyl))tris(1H-indole-1-carboxylate) 在 palladium on activated charcoal 氢溴酸 、 氢气 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 12.03h， 生成 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(6S,12bS)-6-carboxymethyl-quinolizine
  参考文献：
  名称：

  Asymmetric synthesis of indolo[2,3-a]quinolizidin-2-ones - congeners to yohimbine-type alkaloids

  摘要：

  Schiff bases derived from tryptophan methyl ester and tryptamine react with Danishefkys diene in the presence of ZnCl2 to give enaminones which are subsequently transformed into indolo[2,3-a]quinolizidin-2-ones by acid-catalyzed cyclization. These tetracyclic aminoketones serve as viable intermediates in the construction of complex alkaloids, e. g. reserpine and deserpidine, and analogues thereof.

  DOI：

  10.1016/s0040-4020(01)80309-4

文献信息

• Access to Electron-Rich Arene-Fused Hexahydroquinolizinones through a Gold-Catalysis-Initiated Cascade Process
  作者：Lianzhu Liu、Liming Zhang

  DOI：10.1002/anie.201203303

  日期：2012.7.16

  Golden Cascade: With a tethered, electron‐rich arene as the internal nucleophile, a gold‐catalyzed amide cyclization to an alkyne initiates a cascade process that ends with a Ferrier rearrangement. Electron‐rich arene‐bearing hexahydroquinolizin‐2‐ones are formed in good yields and can be converted into indole alkaloids in only a few steps.

  黄金级联：以束缚的、富电子的芳烃作为内部亲核试剂，金催化的酰胺环化成炔引发级联过程，以费里尔重排结束。富含电子的芳烃六氢喹啉-2-酮以良好的产率形成，只需几步即可转化为吲哚生物碱。
• Asymmetric synthesis of indolo[2,3-a]quinolizidin-2-ones - congeners to yohimbine-type alkaloids
  作者：Herbert Waldmann、auMatthias Braun、Markus Weymann、Markus Gewehr

  DOI：10.1016/s0040-4020(01)80309-4

  日期：1993.1

  Schiff bases derived from tryptophan methyl ester and tryptamine react with Danishefkys diene in the presence of ZnCl2 to give enaminones which are subsequently transformed into indolo[2,3-a]quinolizidin-2-ones by acid-catalyzed cyclization. These tetracyclic aminoketones serve as viable intermediates in the construction of complex alkaloids, e. g. reserpine and deserpidine, and analogues thereof.