3-(3,4-dimethoxy-phenyl)-1-(3-methyl-butyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid allylamide

• 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: 3-(3,4-dimethoxy-phenyl)-1-(3-methyl-butyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid allylamide
• 英文别名: 3-(3,4-dimethoxyphenyl)-1-(3-methylbutyl)-5-oxo-N-prop-2-enyl-2H-pyrrole-2-carboxamide
• 化学式: C₂₁H₂₈N₂O₄
• 分子量: 372.464
• InChiKey: UTGLBMMCZXGBHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3',4'-dimethoxyphenylglyoxal 在 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.5h， 生成 3-(3,4-dimethoxy-phenyl)-1-(3-methyl-butyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid allylamide
  参考文献：
  名称：

  Highly Substituted Pyrrolidinones and Pyridones by 4-CR/2-CR Sequence

  摘要：

  By combining a Ugi four-component reaction of isocyanides, phosphonoacetic acids, primary amines, and glyoxals or alternatively 3-keto aldehydes with a subsequent Wittig ring-closing reaction (using the Horner/Wadsworth/Emmons variant (HWE)), highly substituted 5-oxo-2,5dihydro-1H-pyrrole-2-carboxylic acid amides and 6-oxo-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid amides can be assembled, respectively. The corresponding tandem of a Passerini reaction on 3-keto aldehydes and subsequent Wittig ring closure does not afford the expected six-membered 6-oxo-3,6-dihydro-2H-pyran-2-carboxylic acid amides but instead leads to the formation of 4-oxo-pent-2-enoic acid amides via an elimination route.

  DOI：

  10.1021/ol035787n

文献信息

• Highly Substituted Pyrrolidinones and Pyridones by 4-CR/2-CR Sequence
  作者：Barbara Beck、Anne Picard、Eberhardt Herdtweck、Alexander Dömling

  DOI：10.1021/ol035787n

  日期：2004.1.1

  By combining a Ugi four-component reaction of isocyanides, phosphonoacetic acids, primary amines, and glyoxals or alternatively 3-keto aldehydes with a subsequent Wittig ring-closing reaction (using the Horner/Wadsworth/Emmons variant (HWE)), highly substituted 5-oxo-2,5dihydro-1H-pyrrole-2-carboxylic acid amides and 6-oxo-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid amides can be assembled, respectively. The corresponding tandem of a Passerini reaction on 3-keto aldehydes and subsequent Wittig ring closure does not afford the expected six-membered 6-oxo-3,6-dihydro-2H-pyran-2-carboxylic acid amides but instead leads to the formation of 4-oxo-pent-2-enoic acid amides via an elimination route.