6-methyl-11H-isoindolo[2',1':4,5]pyrazino[1,2-a]indol-13-one | 1250829-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡嗪类
• 英文名称: 6-methyl-11H-isoindolo[2',1':4,5]pyrazino[1,2-a]indol-13-one
• 英文别名: 2-Methyl-1,11-diazapentacyclo[11.7.0.03,11.04,9.015,20]icosa-2,4,6,8,13,15,17,19-octaen-12-one
• CAS: 1250829-79-8
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: JVCYFDKTHQPZHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(2-iodobenzyl)-4-methylpyrazino[1,2-a]indol-1(2H)-one 在 四丁基氯化铵 、 potassium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以64%的产率得到6-methyl-11H-isoindolo[2',1':4,5]pyrazino[1,2-a]indol-13-one
  参考文献：
  名称：

  Tunable Pd-Catalyzed Cyclization of Indole-2-carboxylic Acid Allenamides: Carboamination vs Microwave-Assisted Hydroamination

  摘要：

  A variety or 3-vinyl-subtituted imidazo[1.5-a]indole derivatives were synthesized by intramolecular Pd-catalyzed cyclization oh the title allenamides through either a domino carbopalladation/exo-cyclization process or a novel hydroamination reaction that proceeds smoothly under microwave irradiation Both the observed pathways involve a pi-allyl-palladmin(II) complex arising from insertion of the allelic group into it palladium(II) species. the latter being formed In situ by the intervention of an aryl iodide or of the N-H group In both cases the role of nucleophile is covered by the Indole nitrogen

  DOI：

  10.1021/jo101501u

文献信息

• Tunable Pd-Catalyzed Cyclization of Indole-2-carboxylic Acid Allenamides: Carboamination vs Microwave-Assisted Hydroamination
  作者：Egle M. Beccalli、Alice Bernasconi、Elena Borsini、Gianluigi Broggini、Micol Rigamonti、Gaetano Zecchi

  DOI：10.1021/jo101501u

  日期：2010.10.15

  A variety or 3-vinyl-subtituted imidazo[1.5-a]indole derivatives were synthesized by intramolecular Pd-catalyzed cyclization oh the title allenamides through either a domino carbopalladation/exo-cyclization process or a novel hydroamination reaction that proceeds smoothly under microwave irradiation Both the observed pathways involve a pi-allyl-palladmin(II) complex arising from insertion of the allelic group into it palladium(II) species. the latter being formed In situ by the intervention of an aryl iodide or of the N-H group In both cases the role of nucleophile is covered by the Indole nitrogen