3-(1-hydroxyethyl)-2-(methylamino)-11-phenyl-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizin-4(12H)-one

• 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: 3-(1-hydroxyethyl)-2-(methylamino)-11-phenyl-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizin-4(12H)-one
• 英文别名: (2S,3R,12bS)-3-((S)-1-hydroxyethyl)-2-(methylamino)-11-phenyl-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizin-4(12H)-one；(2S,3R,12bS)-3-[(1S)-1-hydroxyethyl]-2-(methylamino)-11-phenyl-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-4-one
• 化学式: C₂₄H₂₇N₃O₂
• 分子量: 389.497
• InChiKey: WMIUINFSVUZIRO-CXTHYWKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-hydroxyethyl)-2-(methylamino)-11-phenyl-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizin-4(12H)-one 、 天然芥菜籽油 以 二氯甲烷 为溶剂， 反应 1.5h， 以89%的产率得到3-allyl-1-(3-(1-hydroxyethyl)-4-oxo-11-phenyl-1,2,3,4,6,7,12,12b-octahydroindolo-[2,3-a]quinolizin-2-yl)-1-methylthiourea
  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-3,3a,6,7,12,12b,13,13a-octahydroindolo[2,3-a]isoxazolo[4,3-g]quinolizin-4(1H)-one 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以71%的产率得到3-(1-hydroxyethyl)-2-(methylamino)-11-phenyl-1,2,3,6,7,12b-hexahydroindolo[2,3-a]quinolizin-4(12H)-one
  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

• 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.