N-<2-(indol-3-yl)ethyl>-2,3-didehydro-4-oxo-6- piperidine | 146560-23-8

• 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: N-<2-(indol-3-yl)ethyl>-2,3-didehydro-4-oxo-6- piperidine
• 英文别名: 2-(4-chlorophenyl)-1-[2-(1H-indol-3-yl)ethyl]-2,3-dihydropyridin-4-one
• CAS: 146560-23-8
• 化学式: C₂₁H₁₉ClN₂O
• 分子量: 350.848
• InChiKey: CMXVCKNCSYCQFO-UHFFFAOYSA-N

物化性质

• 沸点：
  573.3±50.0 °C(predicted)
• 密度：
  1.279±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<2-(indol-3-yl)ethyl>-2,3-didehydro-4-oxo-6- piperidine 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-4-(p-chlorophenyl) quinolizine 、 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-4-(p-chlorophenyl) 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
• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 [1-(4-Chloro-phenyl)-meth-(E)-ylidene]-[2-(1H-indol-3-yl)-ethyl]-amine 在 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以79%的产率得到N-<2-(indol-3-yl)ethyl>-2,3-didehydro-4-oxo-6- piperidine
  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

• 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.