methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate | 219589-99-8

• 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: methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate
• 英文别名: methyl (2S,3aS,5S,11bR)-3-benzyl-5-but-1-en-2-yl-2-carbamoyl-1,2,3a,4,5,7-hexahydropyrrolo[2,3-d]carbazole-6-carboxylate
• CAS: 219589-99-8
• 化学式: C₂₈H₃₁N₃O₃
• 分子量: 457.572
• InChiKey: FMUKBUMKZOGBGI-CBGTVWSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 在 palladium on activated charcoal 四氧化锇 、 钾硼氢 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 17.67h， 生成 20-epi-lochneridine
  参考文献：
  名称：

  Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 11. Total Syntheses of (−)-Lochneridine and (−)- and Racemic 20-epi-Lochneridine

  摘要：

  Enantioselective syntheses of (-)-lochneridine (1) and (-)-epi-lochneridine (2) were obtained by two alternative C-20 diastereoselective syntheses of the respective pentacyclic (3aS,5S,11bR)-methyl 12-oxo-3,5-ethano-2,3,3a,4,5,7-hexahydro-3H-pyrrolo[2,3-d]carbazole-6-carboxylate ((-)-8) and tetracyclic methyl (2S,3aS,5R,11bR))-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo[2,3d]carbazole-6-carboxylate ((-)-12b) precursors from tryptophan derived 2-[(methoxycarbonyl)methyl]3-[2(S)-(methoxy or benzyloxycarbonyl)-2-(N-b-benzyl)aminoethyl]indole (15 or 16). While a modified Grignard reaction of the ketone (-)-8 provided (-)-lochneridine (1), dihydroxylation and cyclization of the olefin (-)-12b gave its C-20 epimer (2).

  DOI：

  10.1021/jo981401o
• 作为产物：
  描述：

  (E)-4-methylenehex-2-enal 在 氨 、 对苯二酚 、 苯甲酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 37.0h， 生成 methyl (2S,3aS,5R,11bR)-2-(aminocarbonyl)-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo<2,3-d>carbazole-6-carboxylate
  参考文献：
  名称：

  Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 11. Total Syntheses of (−)-Lochneridine and (−)- and Racemic 20-epi-Lochneridine

  摘要：

  Enantioselective syntheses of (-)-lochneridine (1) and (-)-epi-lochneridine (2) were obtained by two alternative C-20 diastereoselective syntheses of the respective pentacyclic (3aS,5S,11bR)-methyl 12-oxo-3,5-ethano-2,3,3a,4,5,7-hexahydro-3H-pyrrolo[2,3-d]carbazole-6-carboxylate ((-)-8) and tetracyclic methyl (2S,3aS,5R,11bR))-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo[2,3d]carbazole-6-carboxylate ((-)-12b) precursors from tryptophan derived 2-[(methoxycarbonyl)methyl]3-[2(S)-(methoxy or benzyloxycarbonyl)-2-(N-b-benzyl)aminoethyl]indole (15 or 16). While a modified Grignard reaction of the ketone (-)-8 provided (-)-lochneridine (1), dihydroxylation and cyclization of the olefin (-)-12b gave its C-20 epimer (2).

  DOI：

  10.1021/jo981401o

文献信息

• Syntheses of Strychnan- and Aspidospermatan-Type Alkaloids. 11. Total Syntheses of (−)-Lochneridine and (−)- and Racemic 20-<i>epi</i>-Lochneridine
  作者：Martin E. Kuehne、Feng Xu

  DOI：10.1021/jo981401o

  日期：1998.12.1

  Enantioselective syntheses of (-)-lochneridine (1) and (-)-epi-lochneridine (2) were obtained by two alternative C-20 diastereoselective syntheses of the respective pentacyclic (3aS,5S,11bR)-methyl 12-oxo-3,5-ethano-2,3,3a,4,5,7-hexahydro-3H-pyrrolo[2,3-d]carbazole-6-carboxylate ((-)-8) and tetracyclic methyl (2S,3aS,5R,11bR))-3-benzyl-2,3,3a,4,5,7-hexahydro-5-(2-(1-butenyl))-1H-pyrrolo[2,3d]carbazole-6-carboxylate ((-)-12b) precursors from tryptophan derived 2-[(methoxycarbonyl)methyl]3-[2(S)-(methoxy or benzyloxycarbonyl)-2-(N-b-benzyl)aminoethyl]indole (15 or 16). While a modified Grignard reaction of the ketone (-)-8 provided (-)-lochneridine (1), dihydroxylation and cyclization of the olefin (-)-12b gave its C-20 epimer (2).