2-((methylamino)-11-phenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-3-yl)ethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-((methylamino)-11-phenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-3-yl)ethanol
• 英文别名: (S)-1-((2S,3R,12bS)-2-(methylamino)-11-phenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-3-yl)ethanol；(1S)-1-[(2S,3R,12bS)-2-(methylamino)-11-phenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-3-yl]ethanol
• 化学式: C₂₄H₂₉N₃O
• 分子量: 375.514
• InChiKey: URWFPHSPMQZEDQ-JNHSIYEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  51.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((methylamino)-11-phenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-3-yl)ethanol 、 环己基异氰酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以76%的产率得到3-cyclohexyl-1-(3-(1-hydroxyethyl)-11-phenyl-1,2,3,4,6,7,12,12b-octahydroindolo-[2,3-a]quinolizin-2-yl)-1-methylurea
  参考文献：
  名称：

  Multicomponent Assembly Processes for the Synthesis of Diverse Yohimbine and Corynanthe Alkaloid Analogues

  摘要：

  A strategy involving a Mannich-type multi-component assembly process followed by a 1,3-dipolar cycloaddition has been developed for the rapid and efficient construction of parent heterocyclic scaffolds bearing indole and isoxazolidine rings. These key intermediates were then readily elaborated using well-established protocols for refunctionalization and cross-coupling to access a diverse 180-member library of novel pentacyclic and tetracyclic compounds related to the Yohimbine and Corynanthe alkaloids. Several other new multicomponent assembly processes were developed to access dihydro-beta-carboline-fused benzodiazepines, pyrimidinediones, and rutaecarpine derivatives.

  DOI：

  10.1021/co400055b
• 作为产物：
  描述：

  1,3-dimethyl-11-phenyl-1,3,3a,4,6,7,12,12b,13,13a-decahydroindolo[2,3-a]isoxazolo-[4,3-g]quinolizine 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到2-((methylamino)-11-phenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-3-yl)ethanol
  参考文献：
  名称：

  Multicomponent Assembly Processes for the Synthesis of Diverse Yohimbine and Corynanthe Alkaloid Analogues

  摘要：

  A strategy involving a Mannich-type multi-component assembly process followed by a 1,3-dipolar cycloaddition has been developed for the rapid and efficient construction of parent heterocyclic scaffolds bearing indole and isoxazolidine rings. These key intermediates were then readily elaborated using well-established protocols for refunctionalization and cross-coupling to access a diverse 180-member library of novel pentacyclic and tetracyclic compounds related to the Yohimbine and Corynanthe alkaloids. Several other new multicomponent assembly processes were developed to access dihydro-beta-carboline-fused benzodiazepines, pyrimidinediones, and rutaecarpine derivatives.

  DOI：

  10.1021/co400055b

文献信息

• Diversity oriented synthesis: concise entry to novel derivatives of Yohimbine and Corynanthe alkaloids
  作者：Zhiqian Wang、Kyosuke Kaneda、Zhenglai Fang、Stephen F. Martin

  DOI：10.1016/j.tetlet.2011.10.115

  日期：2012.2

  A novel MCAP-cycloaddition sequence has been applied to the facile synthesis of p-carboline intermediates to gain rapid access to novel derivatives of Yohimbine-like and Corynanthe-like compounds that may be easily diversified by cross-coupling reactions and N-derivatizations to generate small compound libraries. (C) 2011 Elsevier Ltd. All rights reserved.
• Multicomponent Assembly Processes for the Synthesis of Diverse <i>Yohimbine</i> and <i>Corynanthe</i> Alkaloid Analogues
  作者：Brett A. Granger、Zhiqian Wang、Kyosuke Kaneda、Zhenglai Fang、Stephen F. Martin

  DOI：10.1021/co400055b

  日期：2013.7.8

  A strategy involving a Mannich-type multi-component assembly process followed by a 1,3-dipolar cycloaddition has been developed for the rapid and efficient construction of parent heterocyclic scaffolds bearing indole and isoxazolidine rings. These key intermediates were then readily elaborated using well-established protocols for refunctionalization and cross-coupling to access a diverse 180-member library of novel pentacyclic and tetracyclic compounds related to the Yohimbine and Corynanthe alkaloids. Several other new multicomponent assembly processes were developed to access dihydro-beta-carboline-fused benzodiazepines, pyrimidinediones, and rutaecarpine derivatives.