(E)-2-(5-bromo-2-but-2-enoyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)acetaldehyde | 1354549-85-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (E)-2-(5-bromo-2-but-2-enoyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)acetaldehyde
• 英文别名: (E)-5-bromo-N-but-2-enoyl-2,3,4,9-tetrahydro-1H-β-carbolin-1-ylacetaldehyde
• CAS: 1354549-85-1
• 化学式: C₁₇H₁₇BrN₂O₂
• 分子量: 361.238
• InChiKey: LALXPVZIEPXGMU-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(5-bromo-2-but-2-enoyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)acetaldehyde 在 sodium tetrahydroborate 、 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 、 nickel(II) chloride hexahydrate 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 23.25h， 生成 N-(3-(1-hydroxyethyl)-8-phenyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-N-methylcyclohexanecarboxamide
  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：

  N-formyl-4-bromotryptamine 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (E)-2-(5-bromo-2-but-2-enoyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)acetaldehyde
  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