N,N,1-tri(prop-2-ynyl)-1H-pyrrole-2-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N,1-tri(prop-2-ynyl)-1H-pyrrole-2-carboxamide
• 英文别名: N,N,1-tris(prop-2-ynyl)pyrrole-2-carboxamide
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: OOUPWVBUZBBJFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 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-(三氯乙酰)吡咯 在 氨 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.67h， 生成 N,N,1-tri(prop-2-ynyl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization

  摘要：

  A novel and efficient synthesis of N-substituted pyrrolo-pyrazinone derivatives has been developed. A trichloroacetyl group connected to the pyrrole ring was converted into the desired carboxamide derivatives. Promoted by NaH, the pyrrole carboxamide derivatives underwent a tandem reaction with propargyl bromide to afford pyrrolo-pyrazinones with high efficiency under very mild conditions. The mechanism for the formation of the products is discussed and supported by DFT calculations. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.044

文献信息

• Selective synthesis of N-substituted pyrrolo[1,2-a]pyrazin-1(2H)-one derivatives via alkyne cyclization
  作者：Yasin Çetinkaya、Metin Balci

  DOI：10.1016/j.tetlet.2014.10.044

  日期：2014.12

  A novel and efficient synthesis of N-substituted pyrrolo-pyrazinone derivatives has been developed. A trichloroacetyl group connected to the pyrrole ring was converted into the desired carboxamide derivatives. Promoted by NaH, the pyrrole carboxamide derivatives underwent a tandem reaction with propargyl bromide to afford pyrrolo-pyrazinones with high efficiency under very mild conditions. The mechanism for the formation of the products is discussed and supported by DFT calculations. (C) 2014 Elsevier Ltd. All rights reserved.