(1S,12bS)-1-(2,2'-diethoxycarbonyl-2'-hydroxymethyl-ethyl)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine | 135099-86-4

• 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: (1S,12bS)-1-(2,2'-diethoxycarbonyl-2'-hydroxymethyl-ethyl)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
• 英文别名: diethyl 2-[[(1S,12bS)-1-ethyl-3,4,6,7,12,12b-hexahydro-2H-indolo[2,3-a]quinolizin-1-yl]methyl]-2-(hydroxymethyl)propanedioate
• CAS: 135099-86-4
• 化学式: C₂₆H₃₆N₂O₅
• 分子量: 456.582
• InChiKey: ZULKAZQQNIINIS-RDGATRHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  91.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,12bS)-1-(2,2'-diethoxycarbonyl-2'-hydroxymethyl-ethyl)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine 在 氢氧化钾 、 ammonium hydroxide 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 ethyl (1S,12bS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-(2'-hydroxyimino)propionate
  参考文献：
  名称：

  五环体系、吲哚并[2,3-a][1,2]恶嗪并[5,6-i]喹嗪和吲哚[2,3-a]吡喃并[3,2-i]喹嗪的合成及其应用用于合成 Eburnamine-Vincamine 生物碱

  摘要：

  15a-Ethyl-14-carboxylic esters of the title pentacycles (6) and (8) were prepared via Wenkert's enamine (4). Both compounds can be readily transformed into indoloquinolizinylpyruvate oxime esters (5), key intermediates for the synthesis of vincamine alkaloids. The ring/chain equilibrium observed for compounds (6) and (8) was studied by UV and NMR spectroscopic methods.

  DOI：

  10.3987/com-00-8875
• 作为产物：
  描述：

  diethyl 15aS-ethyl-2,3,6,11,15,15a-hexahydro-1H,5H-indolo[2,3-a]pyrano[3,2-i]quinolizine-14,14-(13H)-dicarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以65%的产率得到(1S,12bS)-1-(2,2'-diethoxycarbonyl-2'-hydroxymethyl-ethyl)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
  参考文献：
  名称：

  五环体系、吲哚并[2,3-a][1,2]恶嗪并[5,6-i]喹嗪和吲哚[2,3-a]吡喃并[3,2-i]喹嗪的合成及其应用用于合成 Eburnamine-Vincamine 生物碱

  摘要：

  15a-Ethyl-14-carboxylic esters of the title pentacycles (6) and (8) were prepared via Wenkert's enamine (4). Both compounds can be readily transformed into indoloquinolizinylpyruvate oxime esters (5), key intermediates for the synthesis of vincamine alkaloids. The ring/chain equilibrium observed for compounds (6) and (8) was studied by UV and NMR spectroscopic methods.

  DOI：

  10.3987/com-00-8875

文献信息

• Synthesis and Evaluation of 2′-Hydroxyethyl <i>trans-</i>Apovincaminate Derivatives as Antioxidant and Cognitive Enhancer Agents
  作者：András Nemes、László Czibula、Csaba Szántay, Jr.、Anikó Gere、Béla Kiss、Judit Laszy、István Gyertyán、Zsolt Szombathelyi、Csaba Szántay

  DOI：10.1021/jm070618k

  日期：2008.2.1

  A series of trans-2'-hydroxyethyl and 2'-acyloxyethyl apovincaminates 4b-f and 7b-f has been synthesized and evaluated for their antioxidant and antiamnesic effects. The new esters were prepared from 4a and 7a ethyl esters or from the corresponding carboxylic acid sodium salt. For starting materials 11a,b, a new stereoselective trans-reduction was elaborated. From the combined results of the data obtained from in vitro and in vivo tests and examination of the metabolism, (3R,16S)-2'-hydroxyethyl apovincaminate (7b, RGH-10885) was identified as the most promising compound, owing to its potent neuroprotective and antiamnesic activities. The in vivo effectiveness of selected compounds on the cognitive functions was studied in a one-trial passive avoidance task and a water-labyrinth test.
• Synthesis of Pentacyclic Ring Systems, Indolo[2,3-a][1,2]oxazino[5,6-i]quinolizine and Indolo[2,3-a]pyrano[3,2-i]quinolizine, and Their Application for the Synthesis of Eburnamine-Vincamine Alkaloids
  作者：András Nemes、János Kreidl、László Czibula、Katalin Nógrádi、Mária Farkas、Csaba Szántay Jr.、Gábor Tárkányi、Gábor Balogh、Ida Juhász、Alajos Kálmán、László Párkányi

  DOI：10.3987/com-00-8875

  日期：——

  15a-Ethyl-14-carboxylic esters of the title pentacycles (6) and (8) were prepared via Wenkert's enamine (4). Both compounds can be readily transformed into indoloquinolizinylpyruvate oxime esters (5), key intermediates for the synthesis of vincamine alkaloids. The ring/chain equilibrium observed for compounds (6) and (8) was studied by UV and NMR spectroscopic methods.