N-<(S)-1-carboxymethyl-2-(indol-3-yl)ethyl>-4-oxo-2,3-didehydro-piperidine | 146560-09-0

• 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)-1-carboxymethyl-2-(indol-3-yl)ethyl>-4-oxo-2,3-didehydro-piperidine
• 英文别名: N-((S)-1-Carboxymethyl-2-ethyl)-4-oxo-2,3-didehydropiperidine；methyl (2S)-3-(1H-indol-3-yl)-2-(4-oxo-2,3-dihydropyridin-1-yl)propanoate
• CAS: 146560-09-0
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: JOJXSQXMWIEWFW-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 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)-1-carboxymethyl-2-(indol-3-yl)ethyl>-4-oxo-2,3-didehydro-piperidine 在 吡啶 、 ammonium hydroxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 氢溴酸 、 氯化二乙基铝 、 1-羟基苯并三唑 、 对甲苯磺酸 、 溶剂黄146 、 三氟乙酸酐 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 24.86h， 生成 1,2,3,4,6,7,12,12b-octahydro-2-oxoindolo<2,3-a>-(12bS)-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：

  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 氢气 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 N-<(S)-1-carboxymethyl-2-(indol-3-yl)ethyl>-4-oxo-2,3-didehydro-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 highly functionalized tetracyclic indole bases embodying the basic skeleton of yohimbine- and reserpine type alkaloids
  作者：Ralf Lock、Herbert Waldmann

  DOI：10.1016/0040-4039(96)00388-7

  日期：1996.4

  Schiff bases derived from tryptophan methyl ester react with differently substituted electron-rich siloxy dienes in the presence of achiral or chiral boric acid esters to give enaminones 5 and 6 with high diastereomer ratios (up to >98:2). These intermediates are converted into highly functionalized indoloquinolizines 14 and 15 by means of a new method which employs the transformation of vinylogous

  衍生自色氨酸甲酯的席夫碱在非手性或手性硼酸酯的存在下与不同取代的富电子的甲硅烷氧基二烯反应，得到具有高非对映异构体比率（最高> 98：2）的烯胺酮5和6。通过一种新方法将这些中间体转化为高度官能化的吲哚并喹唑酮14和15，该方法采用乙烯基酰胺转化为乙烯基氯甲基胺并将其随后转化为乙烯基亚氨基酰氯作为关键步骤。
• Enantioselective Construction of Highly Functionalized Indoloquinolizines—congeners to Polycyclic Indole Alkaloids
  作者：Ralf Lock、Herbert Waldmann

  DOI：10.1002/chem.19970030122

  日期：1997.1

  AbstractIndolo[2,3‐a]quinolizines have been prepared in enantiomerically pure form by a very short and efficient synthetic sequence consisting of a) formation of imines of tryptophan esters, b) their enantioselective reaction with substituted silyloxydienes mediated by a chiral or an achiral boron Lewis acid, and c) subsequent ring closure initiated by conversion of the generated vinylogous amides into vinylogous imidoyl chlorides. With this strategy various substituents can be incorporated directly into the 1‐position of the heterocyclic framework of complex indole alkaloids by the choice of an appropriate silyloxydiene, so that subsequent derivatization of the alkaloid precursor at this position is rendered unnecessary.