3-[3-(4-ethoxycarbonylphenyl)-3-oxoprop-1-en-2-yl]-2-methyl-2,3-dihydro-1H-imidazo[1,5-a]indol-1-one | 1250829-75-4

• 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-[3-(4-ethoxycarbonylphenyl)-3-oxoprop-1-en-2-yl]-2-methyl-2,3-dihydro-1H-imidazo[1,5-a]indol-1-one
• 英文别名: ethyl 4-[2-(2-methyl-3-oxo-1H-imidazo[1,5-a]indol-1-yl)prop-2-enoyl]benzoate
• CAS: 1250829-75-4
• 化学式: C₂₃H₂₀N₂O₄
• 分子量: 388.423
• InChiKey: FKOMRHNDZUAGOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-methyl-N-(propa-1,2-dienyl)-1H-indole-2-carboxamide 、 对碘苯甲酸乙酯 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以33%的产率得到3-[3-(4-ethoxycarbonylphenyl)-3-oxoprop-1-en-2-yl]-2-methyl-2,3-dihydro-1H-imidazo[1,5-a]indol-1-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