(6S,11bR)-6-(hydroxymethyl)-9,10-dimethoxy-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-4-one | 459870-37-2

• 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: (6S,11bR)-6-(hydroxymethyl)-9,10-dimethoxy-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-4-one
• CAS: 459870-37-2
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: BBTSYOYWIZKCCC-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6S,11bR)-6-(hydroxymethyl)-9,10-dimethoxy-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-4-one 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以70%的产率得到(6S,11bR)-9,10-Dimethoxy-4-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-6-carbaldehyde
  参考文献：
  名称：

  Complementary routes for the stereoselective synthesis of functionalized benzoquinolizidine targets

  摘要：

  We report new and complementary routes for the highly stereoselective construction of functionalized benzoquinolizidine targets from readily available, non-racemic chiral templates. The methods developed allow us to predetermine relative product stereochemistries by judicious choice of substrate sub-structure, and provide ready access to alternative stereoisomers. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.035
• 作为产物：
  描述：

  (2S)-2-amino-3-(3,4-dimethoxyphenyl)-1-propanol 在 四氯化钛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 (6S,11bR)-6-(hydroxymethyl)-9,10-dimethoxy-1,2,3,6,7,11b-hexahydrobenzo[a]quinolizin-4-one
  参考文献：
  名称：

  Stereoselective synthesis of isoquinoline derivatives from bicyclic lactam templates

  摘要：

  We report a novel, facile and stereoselective approach to a tricyclic tetrahydroisoquinoline ring system from readily available, non-racemic, bicyclic lactam substrates. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00628-7

文献信息

• Stereocontrolled Generation of Benzo[a]- and Indolo[2,3-a]quinolizidines from (S)-Tryptophanol and (S)-(3,4-Dimethoxyphenyl)alaninol-Derived Lactams
  作者：Maria Pérez、Federica Arioli、Gianna Rigacci、Maria M. M. Santos、Arantxa Gómez-Esqué、Carmen Escolano、Pedro Florindo、Carlos Ramos、Joan Bosch、Mercedes Amat

  DOI：10.1002/ejoc.201100294

  日期：2011.7

  Financial support from the Spanish Ministerio de Ciencia e Innovacion (MICINN) (project CTQ2009-07021/BQU), from the Portuguese Fundacao para a Ciencia e a Tecnologia (FCT) (project PTDC/QUI-QUI/111664/2009), and from the Spanish-Portuguese Integrated Action (AIB2010PT-00324 and E-07/11) is gratefully acknowledged. Thanks are also due to the AGAUR (Generalitat de Catalunya) for grant 2009-SGR-1111

  来自西班牙国家科学与创新部长 (MICINN)（项目 CTQ2009-07021/BQU）、葡萄牙 Fundacao para a Ciencia ea Tecnologia (FCT)（项目 PTDC/QUI-QUI/111664/2009）以及来自非常感谢西班牙-葡萄牙综合行动（AIB2010PT-00324 和 E-07/11）。还要感谢 AGAUR (Generalitat de Catalunya) 授予 2009-SGR-1111 的资助，MICINN 授予 CR 的奖学金，以及 Leonardo da Vinci 计划（Unipharma 毕业生 5）授予 GR 的流动性资助
• Complementary routes for the stereoselective synthesis of functionalized benzoquinolizidine targets
  作者：Steven M. Allin、Liam J. Duffy、Philip C. Bulman Page、Vickie McKee、Mark Edgar、Michael J. McKenzie、Mercedes Amat、Oriol Bassas、Maria M.M. Santos、Joan Bosch

  DOI：10.1016/j.tetlet.2006.06.035

  日期：2006.8

  We report new and complementary routes for the highly stereoselective construction of functionalized benzoquinolizidine targets from readily available, non-racemic chiral templates. The methods developed allow us to predetermine relative product stereochemistries by judicious choice of substrate sub-structure, and provide ready access to alternative stereoisomers. (c) 2006 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of isoquinoline derivatives from bicyclic lactam templates
  作者：Steven M. Allin、Darshan G. Vaidya、Stella L. James、James E. Allard、Timothy A.D. Smith、Vickie McKee、William P. Martin

  DOI：10.1016/s0040-4039(02)00628-7

  日期：2002.5

  We report a novel, facile and stereoselective approach to a tricyclic tetrahydroisoquinoline ring system from readily available, non-racemic, bicyclic lactam substrates. (C) 2002 Elsevier Science Ltd. All rights reserved.