N-methyl-N-propargyl-7-nitro-1H-indole-2-carboxamide | 1250829-40-3

• 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: N-methyl-N-propargyl-7-nitro-1H-indole-2-carboxamide
• 英文别名: N-methyl-7-nitro-N-prop-2-ynyl-1H-indole-2-carboxamide
• CAS: 1250829-40-3
• 化学式: C₁₃H₁₁N₃O₃
• 分子量: 257.249
• InChiKey: OLWJBHURVXXMRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyl-N-propargyl-7-nitro-1H-indole-2-carboxamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.02h， 生成 N-methyl-N-(propa-1,2-dienyl)-7-nitro-1H-indole-2-carboxamide
  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
• 作为产物：
  描述：

  N-甲基炔丙基胺 、 7-硝基吲哚-2-甲酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以74%的产率得到N-methyl-N-propargyl-7-nitro-1H-indole-2-carboxamide
  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