(1R,2S,3S,6S,11R,13R,14S)-6-[(3,4-dimethoxyphenyl)methyl]-4-oxa-7-azapentacyclo[12.2.1.02,13.03,7.03,11]heptadec-15-en-8-one | 1042308-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S,3S,6S,11R,13R,14S)-6-[(3,4-dimethoxyphenyl)methyl]-4-oxa-7-azapentacyclo[12.2.1.02,13.03,7.03,11]heptadec-15-en-8-one
• CAS: 1042308-80-4
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: GJFBGRVCEHYGJU-DUAAMXSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,6S,11R,13R,14S)-6-[(3,4-dimethoxyphenyl)methyl]-4-oxa-7-azapentacyclo[12.2.1.02,13.03,7.03,11]heptadec-15-en-8-one 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以91%的产率得到(5S,10bR,13aR)-8,9-dimethoxy-1,2,5,6,13,13a-hexahydrocyclopenta[e]oxazolo[3,2-a]pyrido[2,1-a]isoquinolinium tetrafluoroborate
  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
• 作为产物：
  描述：

  3-(1-oxo-2,3,3a,4,7,7a-hexahydro-4,7-methanoinden-2-yl)propionic acid 、 (2S)-2-amino-3-(3,4-dimethoxyphenyl)-1-propanol 以 甲苯 为溶剂， 反应 48.0h， 以45%的产率得到(1R,2S,3S,6S,11R,13R,14S)-6-[(3,4-dimethoxyphenyl)methyl]-4-oxa-7-azapentacyclo[12.2.1.02,13.03,7.03,11]heptadec-15-en-8-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

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.