(-)-lochneridine | 5980-01-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 马钱子生物碱
• 英文名称: (-)-lochneridine
• 英文别名: Lochneridine；methyl (1R,11R,12S,17S)-12-ethyl-12-hydroxy-8,14-diazapentacyclo[9.5.2.01,9.02,7.014,17]octadeca-2,4,6,9-tetraene-10-carboxylate
• CAS: 5980-01-8
• 化学式: C₂₀H₂₄N₂O₃
• 分子量: 340.422
• InChiKey: DGKIJZKKTDPACC-CTNSEHHHSA-N

物化性质

• 熔点：
  211-4°C (dec.).
• 比旋光度：
  D26 +607.5° (chloroform)
• 沸点：
  507.7±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-oxo-1H-pyrrolo-<2,3-d>carbazole-6-carboxylate	219650-29-0	C18H18N2O3	310.353

反应信息

• 作为产物：
  描述：

  乙基溴化镁 、 (-)-methyl (2S,3aS,5R,11bR)-3-benzyl-2,3,3a,4,5,7-hexahydro-3,5-ethano-12-oxo-1H-pyrrolo-<2,3-d>carbazole-6-carboxylate 在 cerium(III) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以73%的产率得到(-)-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

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).