(5S,10bR,13aR)-(8,9-dimethoxy-2,3,5,6,13,13a-hexahydro-1H-cyclopenta[2,3]pyrido[2,1-a]isoquinolin-5-yl)methanol | 1042308-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (5S,10bR,13aR)-(8,9-dimethoxy-2,3,5,6,13,13a-hexahydro-1H-cyclopenta[2,3]pyrido[2,1-a]isoquinolin-5-yl)methanol
• 英文别名: [(1R,9S,14R)-4,5-dimethoxy-10-azatetracyclo[8.7.0.01,14.02,7]heptadeca-2,4,6,16-tetraen-9-yl]methanol
• CAS: 1042308-86-0
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: VASNEKAHBCNKSX-DOXZYTNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5S,10bR,13aR)-8,9-dimethoxy-1,2,5,6,13,13a-hexahydrocyclopenta[e]oxazolo[3,2-a]pyrido[2,1-a]isoquinolinium tetrafluoroborate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 以65%的产率得到(5S,10bR,13aR)-(8,9-dimethoxy-2,3,5,6,13,13a-hexahydro-1H-cyclopenta[2,3]pyrido[2,1-a]isoquinolin-5-yl)methanol
  参考文献：
  名称：

  Asymmetric Synthesis of Tetracyclic Benzo[a]quinolizidine Targets

  摘要：

  We report a novel, facile, and asymmetric approach for the synthesis of polycyclic benzo[a]quinolizidine targets. In the formation of more functionalized derivatives, we have observed the generation of an iminium ether salt intermediate, formed during an unprecedented retro-Diels-Alder/N-acyliminium cyclization cascade. The iminium ether intermediate was isolated in good yield, characterized by X-ray crystallography, and subsequently applied as a synthetic building block.

  DOI：

  10.1021/jo801019h

文献信息

• Asymmetric Synthesis of Tetracyclic Benzo[<i>a</i>]quinolizidine Targets
  作者：Steven M. Allin、Sean N. Gaskell、Mark R. J. Elsegood、William P. Martin

  DOI：10.1021/jo801019h

  日期：2008.8.1

  We report a novel, facile, and asymmetric approach for the synthesis of polycyclic benzo[a]quinolizidine targets. In the formation of more functionalized derivatives, we have observed the generation of an iminium ether salt intermediate, formed during an unprecedented retro-Diels-Alder/N-acyliminium cyclization cascade. The iminium ether intermediate was isolated in good yield, characterized by X-ray crystallography, and subsequently applied as a synthetic building block.