4-(furan-2-ylcarbonyl)-3-hydroxy-5-phenyl-1-(1,3-thiazol-2-yl)-2,5-dihydro-1H-pyrrol-2-one | 919941-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 4-(furan-2-ylcarbonyl)-3-hydroxy-5-phenyl-1-(1,3-thiazol-2-yl)-2,5-dihydro-1H-pyrrol-2-one
• 英文别名: 3-(furan-2-carbonyl)-4-hydroxy-2-phenyl-1-(1,3-thiazol-2-yl)-2H-pyrrol-5-one
• CAS: 919941-90-5
• 化学式: C₁₈H₁₂N₂O₄S
• 分子量: 352.37
• InChiKey: NGNBJUGXFJGHJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(furan-2-ylcarbonyl)-3-hydroxy-5-phenyl-1-(1,3-thiazol-2-yl)-2,5-dihydro-1H-pyrrol-2-one 、 苯肼 以 溶剂黄146 为溶剂， 反应 3.0h， 以35%的产率得到3-(furan-2-yl)-2,4-diphenyl-5-(1,3-thiazol-2-yl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(2H)-one
  参考文献：
  名称：

  Reactions of 5-aryl-4-(hetaren-2-ylcarbonyl)-3-hydroxy-1-(1,3-thiazol-2-yl)-2,5-dihydro-1H-pyrrol-2-ones with hydrazine, phenylhydrazine, and hydroxylamine

  摘要：

  Three-component condensation of methyl 4-(furan-2-yl)- and 4-(thiophen-2-yl)-2,4-dioxobutanoates with aromatic aldehydes and 1,3-thiazol-2-amine afforded 5-aryl-4-(hetaren-2-ylcarbonyl)-3-hydroxy-1-(1,3-thiazol-2-yl)-2,5-dihydro-1H-pyrrol-2-ones. Reactions of the latter with hydrazine and phenylhydrazine gave pyrrolo[3,4-c]pyrazol-6-ones and 3-phenylhydrazones, while the corresponding oximes were obtained in reactions with hydroxylamine.

  DOI：

  10.1134/s1070428015010194
• 作为产物：
  描述：

  4-呋喃-2-基-2,4-二氧代丁酸甲酯 、 2-氨基噻唑 、 苯甲醛 以 溶剂黄146 为溶剂， 以56%的产率得到4-(furan-2-ylcarbonyl)-3-hydroxy-5-phenyl-1-(1,3-thiazol-2-yl)-2,5-dihydro-1H-pyrrol-2-one
  参考文献：
  名称：

  Reactions of 5-aryl-4-(hetaren-2-ylcarbonyl)-3-hydroxy-1-(1,3-thiazol-2-yl)-2,5-dihydro-1H-pyrrol-2-ones with hydrazine, phenylhydrazine, and hydroxylamine

  摘要：

  Three-component condensation of methyl 4-(furan-2-yl)- and 4-(thiophen-2-yl)-2,4-dioxobutanoates with aromatic aldehydes and 1,3-thiazol-2-amine afforded 5-aryl-4-(hetaren-2-ylcarbonyl)-3-hydroxy-1-(1,3-thiazol-2-yl)-2,5-dihydro-1H-pyrrol-2-ones. Reactions of the latter with hydrazine and phenylhydrazine gave pyrrolo[3,4-c]pyrazol-6-ones and 3-phenylhydrazones, while the corresponding oximes were obtained in reactions with hydroxylamine.

  DOI：

  10.1134/s1070428015010194

文献信息

• Approach to the Library of 3-Hydroxy-1,5-dihydro-2<i>H</i>-pyrrol-2-ones through a Three-Component Condensation
  作者：Sergey V. Ryabukhin、Dmitriy M. Panov、Andrey S. Plaskon、Oleksandr O. Grygorenko

  DOI：10.1021/co300082t

  日期：2012.12.10

  A convenient procedure for the parallel synthesis of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones through a three-component condensation of active methylene compounds, aldehydes, and amines was developed. It was shown that the use of acetic acid as the reaction medium was suitable for the considerably reactive substrates with no additional functionalities. The substrates with low reactivity and those possessing carboxylic groups or additional basic centers required the use of DMF as the solvent and chlorotrimethylsilane as the reaction promoter was necessary. More than 3000 pyrrolones were synthesized by the developed procedure. To demonstrate the scope of the described approach 114 library representatives were fully characterized.
• Reactions of 1,5-diaryl-4-heteroyl-3-hydroxy-3-pyrrolin-2-ones with arylamines and butylamine
  作者：V. L. Gein、L. F. Gein、V. S. Platonov、O. V. Bobrovskaya

  DOI：10.1134/s1070363214090072

  日期：2014.9

  1,5-Diaryl-4-[2-thienoyl(furanoyl)]-3-hydroxy-3-pyrrolin-2-ones reacted with aromatic amines to form arylamino-3-pyrrolin-2-ones. Reactions with butylamine occurred via intermediate salt formation followed by their transformation into 3-butylamino-3-pyrrolin-2-ones at heating.