1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bR)-6-carboxymethyl-4-phenyl quinolizine | 146609-57-6

• 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: 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bR)-6-carboxymethyl-4-phenyl quinolizine
• 英文别名: 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo[2,3-a]-(4R,6S,12bR)-6-carboxymethyl-4-phenyl quinolizine；methyl (4S,6S,12bR)-2-oxo-4-phenyl-3,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine-6-carboxylate
• CAS: 146609-57-6；139259-13-5
• 化学式: C₂₃H₂₂N₂O₃
• 分子量: 374.439
• InChiKey: QKQKTOIZYQAIPJ-HBMCJLEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  L-色氨酸甲酯 在 三氟乙酸 magnesium sulfate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bR)-6-carboxymethyl-4-phenyl 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

• Scandium(III)‐Zeolites as New Heterogeneous Catalysts for Imino‐Diels–Alder Reactions
  作者：Andrea Olmos、Benoit Louis、Patrick Pale

  DOI：10.1002/chem.201103624

  日期：2012.4.16

  demonstrates the first zeolite‐catalyzed synthesis of piperidine derivatives, including peptidomimetics and indoloquinolizidine alkaloids. The approach developed utilizes a highly effective one‐pot reaction cascade, through imine formation and imino‐Diels–Alder reactions, promoted by scandium‐loaded zeolites as a heterogeneous catalyst. The methodology described benefits from very low catalyst loadings (≤5 mol %

  这项研究证明了沸石催化的哌啶衍生物的首次合成，包括拟肽和吲哚并喹喔啉生物碱。所开发的方法通过形成亚胺和亚氨基Diels-Alder反应，通过scan载沸石作为非均相催化剂促进了高效的一锅反应级联反应。该方法从非常低的催化剂负载量（≤5摩尔％的Sc描述益处III），市售且容易获得的起始原料，和温和的反应条件。此外，Sc III沸石催化剂可轻松重复使用10次以上，而不会降低效率。
• 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.