N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6S)-2,3-didehydro-4-oxo-6-i-propyl piperidine | 139258-99-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6S)-2,3-didehydro-4-oxo-6-i-propyl piperidine
• 英文别名: methyl (2S)-3-(1H-indol-3-yl)-2-[(2S)-4-oxo-2-propan-2-yl-2,3-dihydropyridin-1-yl]propanoate
• CAS: 139258-99-4
• 化学式: C₂₀H₂₄N₂O₃
• 分子量: 340.422
• InChiKey: FTQAKJVLJYSWKJ-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6S)-2,3-didehydro-4-oxo-6-i-propyl piperidine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bR)-6-carboxymethyl-4-n-propyl quinolizine 、 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(4R,6S,12bS)-6-carboxymethyl-4-i-propyl 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：

  L-色氨酸甲酯 在 magnesium sulfate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 N-<(S)-2-carboxymethyl-2-(indol-3-yl)ethyl>-(6S)-2,3-didehydro-4-oxo-6-i-propyl 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.