3-(Cyclohexylmethyl)-3-carbomethoxy-5(E)-<(4-phenylcyclohex-1-en-1-yl)methylidene>tetrahydrofuran-2-one | 137742-38-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(Cyclohexylmethyl)-3-carbomethoxy-5(E)-<(4-phenylcyclohex-1-en-1-yl)methylidene>tetrahydrofuran-2-one
• 英文别名: 3-(Cyclohexylmethyl)-3-carbomethoxy-5(E)-[(4-phenylcyclohex-1-en-1-yl)methylidene]tetrahydrofuran-2-one；methyl (5Z)-3-(cyclohexylmethyl)-2-oxo-5-[(4-phenylcyclohexen-1-yl)methylidene]oxolane-3-carboxylate
• CAS: 137742-38-2；137742-39-3
• 化学式: C₂₆H₃₂O₄
• 分子量: 408.538
• InChiKey: CWPSRPAIXOUBTM-KQWNVCNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-苯基环己酮 在 二乙酰二(三苯基膦)钯 2,6-二叔丁基-4-甲基吡啶 、 四丁基氯化铵 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.67h， 生成 3-(Cyclohexylmethyl)-3-carbomethoxy-5(E)-<(4-phenylcyclohex-1-en-1-yl)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.