5(E)-<(4-Acetylphenyl)methylidene>tetrahydrofuran-2-one | 137742-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5(E)-<(4-Acetylphenyl)methylidene>tetrahydrofuran-2-one
• 英文别名: 5(E)-[(4-Acetylphenyl)methylidene]tetrahydrofuran-2-one；(5E)-5-[(4-acetylphenyl)methylidene]oxolan-2-one
• CAS: 137742-28-0
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: HIJGFOIBAWVWLL-XYOKQWHBSA-N

物化性质

• 沸点：
  427.5±45.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  炔丙基脲 、 4-溴苯乙酮 在 二乙酰二(三苯基膦)钯 四丁基氯化铵 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以60%的产率得到5(E)-<(4-Acetylphenyl)methylidene>tetrahydrofuran-2-one
  参考文献：
  名称：

  Palladium-catalyzed reaction of vinyl triflates and vinyl/aryl halides with 4-alkynoic acids: regio- and stereoselective synthesis of (E)-.delta.-vinyl/aryl-.gamma.-methylene-.gamma.-butyrolactones

  摘要：

  The palladium-catalyzed reaction of vinyl triflates and vinyl/aryl halides with 4-pentynoic acid, 2,2-disubstituted 4-pentynoic acids, and 5-substituted 4-pentynoic acids produced regio- and stereoselectively the corresponding (E)-delta-vinyl/aryl-gamma-methylene-gamma-butyrolactones in good to high yield. Reactions were carried out in the presence of catalytic amounts of Pd(OAc)2(PPh3)2 or Pd(PPh3)4, Et3N, and n-Bu4NCl. The presence of chloride anions was found to be necessary to obtain the best results. The proposed mechanism involves an intramolecular nucleophilic attack of the carboxylate anion on the palladium-coordinated carbon-carbon triple bond and subsequent reductive elimination of Pd(0) species from the resulting sigma-vinylpalladium complex which regenerates the catalyst and releases the exocyclic enol lactone.

  DOI：

  10.1021/jo00029a035

文献信息

• Palladium-catalyzed reaction of vinyl triflates and vinyl/aryl halides with 4-alkynoic acids: regio- and stereoselective synthesis of (E)-.delta.-vinyl/aryl-.gamma.-methylene-.gamma.-butyrolactones
  作者：Antonio Arcadi、Alfredo Burini、Sandro Cacchi、Monica Delmastro、Fabio Marinelli、Bianca Rosa Pietroni

  DOI：10.1021/jo00029a035

  日期：1992.1

  The palladium-catalyzed reaction of vinyl triflates and vinyl/aryl halides with 4-pentynoic acid, 2,2-disubstituted 4-pentynoic acids, and 5-substituted 4-pentynoic acids produced regio- and stereoselectively the corresponding (E)-delta-vinyl/aryl-gamma-methylene-gamma-butyrolactones in good to high yield. Reactions were carried out in the presence of catalytic amounts of Pd(OAc)2(PPh3)2 or Pd(PPh3)4, Et3N, and n-Bu4NCl. The presence of chloride anions was found to be necessary to obtain the best results. The proposed mechanism involves an intramolecular nucleophilic attack of the carboxylate anion on the palladium-coordinated carbon-carbon triple bond and subsequent reductive elimination of Pd(0) species from the resulting sigma-vinylpalladium complex which regenerates the catalyst and releases the exocyclic enol lactone.