ethyl 15aS-ethyl-2,3,6,11,15,15a-hexahydro-1H,5H-indolo[2,3-a][1,2]oxazino[5,6-i]quinolizine-14-carboxylate | 300661-80-7

• 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: ethyl 15aS-ethyl-2,3,6,11,15,15a-hexahydro-1H,5H-indolo[2,3-a][1,2]oxazino[5,6-i]quinolizine-14-carboxylate
• 英文别名: ethyl (1S,17S)-17-ethyl-21-oxa-3,13,20-triazapentacyclo[11.8.0.01,17.02,10.04,9]henicosa-2(10),4,6,8,19-pentaene-19-carboxylate
• CAS: 300661-80-7
• 化学式: C₂₂H₂₇N₃O₃
• 分子量: 381.475
• InChiKey: DYNWSRWZJZVBNQ-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对甲苯磺酸 、 ethyl 15aS-ethyl-2,3,6,11,15,15a-hexahydro-1H,5H-indolo[2,3-a][1,2]oxazino[5,6-i]quinolizine-14-carboxylate 以 甲苯 为溶剂， 反应 8.0h， 生成
  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：

  1-乙基-2,3,4,6,7,12-六氢吲哚并[2,3-a]喹嗪 在 sodium hydroxide 、 L-酒石酸 、 苄基三乙基氯化铵 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 ethyl 15aS-ethyl-2,3,6,11,15,15a-hexahydro-1H,5H-indolo[2,3-a][1,2]oxazino[5,6-i]quinolizine-14-carboxylate
  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 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.