(5R,10bR,13aR)-5-hydroxymethyl-8,9-dimethoxy-1,2,5,6,11,12,13,13a-octahydrocyclopenta[2,3]pyrido[2,1-a]isoquinolin-3-one | 1042308-63-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (5R,10bR,13aR)-5-hydroxymethyl-8,9-dimethoxy-1,2,5,6,11,12,13,13a-octahydrocyclopenta[2,3]pyrido[2,1-a]isoquinolin-3-one
• 英文别名: (1R,9R,14R)-9-(hydroxymethyl)-4,5-dimethoxy-10-azatetracyclo[8.7.0.01,14.02,7]heptadeca-2,4,6-trien-11-one
• CAS: 1042308-63-3
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: ZBHMAWUUGQEDRU-PJIJBLCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3R,6aR,9aS)-3-(3,4-dimethoxybenzyl)-octahydro-1-oxa-3a-azacyclopenta[d]inden-4-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(5R,10bR,13aR)-5-hydroxymethyl-8,9-dimethoxy-1,2,5,6,11,12,13,13a-octahydrocyclopenta[2,3]pyrido[2,1-a]isoquinolin-3-one
  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