(E)-2-(5-bromo-1-methyl-1H-indole-3-carbonyl)-3-(1H-pyrrol-2-yl)acrylonitrile | 1450842-17-7

• 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: (E)-2-(5-bromo-1-methyl-1H-indole-3-carbonyl)-3-(1H-pyrrol-2-yl)acrylonitrile
• 英文别名: (E)-2-(5-bromo-1H-indole-3-carbonyl)-3-(1-methylpyrrol-2-yl)prop-2-enenitrile
• CAS: 1450842-17-7
• 化学式: C₁₇H₁₂BrN₃O
• 分子量: 354.206
• InChiKey: IGDGQZKGINWAAQ-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二甲基硫 、 (E)-2-(5-bromo-1-methyl-1H-indole-3-carbonyl)-3-(1H-pyrrol-2-yl)acrylonitrile 反应 1.0h， 以85%的产率得到(E)-2-(5-bromo-1-methyl-1H-indole-3-carbonyl)-3-(1-methyl-1H-pyrrol-2-yl)acrylonitrile
  参考文献：
  名称：

  Facile and Green Syntheses of 2-(N-Methylindole-3-carbonyl)-3-(N-methylpyrrol-2-yl)acrylonitriles and a Study of Their Antimicrobial Activities

  摘要：

  Facile and green syntheses of substituted-2-(N-methylindole-3-carbonyl)-3-(N-methyl pyrrol-2-yl) acrylonitriles 6a-d are being reported. L-Proline has been utilized as an efficient and ecofriendly catalyst in aqueous medium for Knoevenagel condensation of pyrrole-2-carboxyaldehyde (1) and its N-methyl derivative (2) with the active methylene compounds 3-cyanoacetylindoles 3a-d at room temperature to afford substituted-2-(1H-indole-3-carbonyl)-3-(1H-pyrrol-2-yl)acrylonitriles 4a-d and substituted-2-(1H-indole-3-carbonyl)-3-(N-methylpyrrol-2-yl) acrylonitriles 5a-d respectively. Subsequently these products were treated with dimethyl sulfate (DMS) in polythylene glycol (PEG)-600 as an efficient and green solvent to afford the corresponding substituted-2-(N-methylindole-3-carbonyl)-3-(N-methylpyrrol-2-yl)acrylonitriles 6a-d. The antibacterial and antifungal activities of 4a-d, 5a-d, and 6a-d have been studied. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2012.744055
• 作为产物：
  描述：

  N-甲基-2-吡咯甲醛 、 3-(5-bromo-1H-indol-3-yl)-3-oxopropanenitrile 在 L-脯氨酸 作用下， 以 水 为溶剂， 反应 1.0h， 以84%的产率得到(E)-2-(5-bromo-1-methyl-1H-indole-3-carbonyl)-3-(1H-pyrrol-2-yl)acrylonitrile
  参考文献：
  名称：

  Facile and Green Syntheses of 2-(N-Methylindole-3-carbonyl)-3-(N-methylpyrrol-2-yl)acrylonitriles and a Study of Their Antimicrobial Activities

  摘要：

  Facile and green syntheses of substituted-2-(N-methylindole-3-carbonyl)-3-(N-methyl pyrrol-2-yl) acrylonitriles 6a-d are being reported. L-Proline has been utilized as an efficient and ecofriendly catalyst in aqueous medium for Knoevenagel condensation of pyrrole-2-carboxyaldehyde (1) and its N-methyl derivative (2) with the active methylene compounds 3-cyanoacetylindoles 3a-d at room temperature to afford substituted-2-(1H-indole-3-carbonyl)-3-(1H-pyrrol-2-yl)acrylonitriles 4a-d and substituted-2-(1H-indole-3-carbonyl)-3-(N-methylpyrrol-2-yl) acrylonitriles 5a-d respectively. Subsequently these products were treated with dimethyl sulfate (DMS) in polythylene glycol (PEG)-600 as an efficient and green solvent to afford the corresponding substituted-2-(N-methylindole-3-carbonyl)-3-(N-methylpyrrol-2-yl)acrylonitriles 6a-d. The antibacterial and antifungal activities of 4a-d, 5a-d, and 6a-d have been studied. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2012.744055

文献信息

• Facile and Green Syntheses of 2-(N-Methylindole-3-carbonyl)-3-(N-methylpyrrol-2-yl)acrylonitriles and a Study of Their Antimicrobial Activities
  作者：G. Thirupathi、M. Venkatanarayana、P. K. Dubey、Y. Bharathi Kumari

  DOI：10.1080/00397911.2012.744055

  日期：2013.11.17

  Facile and green syntheses of substituted-2-(N-methylindole-3-carbonyl)-3-(N-methyl pyrrol-2-yl) acrylonitriles 6a-d are being reported. L-Proline has been utilized as an efficient and ecofriendly catalyst in aqueous medium for Knoevenagel condensation of pyrrole-2-carboxyaldehyde (1) and its N-methyl derivative (2) with the active methylene compounds 3-cyanoacetylindoles 3a-d at room temperature to afford substituted-2-(1H-indole-3-carbonyl)-3-(1H-pyrrol-2-yl)acrylonitriles 4a-d and substituted-2-(1H-indole-3-carbonyl)-3-(N-methylpyrrol-2-yl) acrylonitriles 5a-d respectively. Subsequently these products were treated with dimethyl sulfate (DMS) in polythylene glycol (PEG)-600 as an efficient and green solvent to afford the corresponding substituted-2-(N-methylindole-3-carbonyl)-3-(N-methylpyrrol-2-yl)acrylonitriles 6a-d. The antibacterial and antifungal activities of 4a-d, 5a-d, and 6a-d have been studied. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]