8-bromo-1,3-dimethyl-1,3,3a,6,7,12b,13,13a-octahydroindolo[2,3-a]isoxazolo[4,3-g]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: 8-bromo-1,3-dimethyl-1,3,3a,6,7,12b,13,13a-octahydroindolo[2,3-a]isoxazolo[4,3-g]quinolizin-4(12H)-one
• 英文别名: (3S,3aR,12bS,13aS)-8-bromo-1,3-dimethyl-3,3a,6,7,12,12b,13,13a-octahydroindolo[2,3-a]isoxazolo[4,3-g]quinolizin-4(1H)-one；(2S,4S,7S,8R)-15-bromo-5,7-dimethyl-6-oxa-5,10,20-triazapentacyclo[11.7.0.02,10.04,8.014,19]icosa-1(13),14(19),15,17-tetraen-9-one
• 化学式: C₁₈H₂₀BrN₃O₂
• 分子量: 390.28
• InChiKey: AGCJXBVJZNGJRG-BCZWGYKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-bromo-1,3-dimethyl-1,3,3a,6,7,12b,13,13a-octahydroindolo[2,3-a]isoxazolo[4,3-g]quinolizin-4(12H)-one 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 alane N,N-dimethylethylamine complex 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 18.5h， 生成 1,3-dimethyl-8-phenyl-1,3,3a,4,6,7,12,12b,13,13a-decahydroindolo[2,3-a]isoxazolo[4,3-g]quinolizine
  参考文献：
  名称：

  Diversity oriented synthesis: concise entry to novel derivatives of Yohimbine and Corynanthe alkaloids

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.10.115
• 作为产物：
  描述：

  N-formyl-4-bromotryptamine 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 8-bromo-1,3-dimethyl-1,3,3a,6,7,12b,13,13a-octahydroindolo[2,3-a]isoxazolo[4,3-g]quinolizin-4(12H)-one
  参考文献：
  名称：

  Diversity oriented synthesis: concise entry to novel derivatives of Yohimbine and Corynanthe alkaloids

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.10.115

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.
• 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.