(3E,3aS,5aS,9bS)-3-[(4-fluorophenyl)methylidene]-5a,9-dimethyl-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran-2,8-dione | 1187652-99-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3E,3aS,5aS,9bS)-3-[(4-fluorophenyl)methylidene]-5a,9-dimethyl-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran-2,8-dione
• CAS: 1187652-99-8
• 化学式: C₂₁H₁₉FO₃
• 分子量: 338.378
• InChiKey: PLDHVWJMNWWIHS-RMQHDPHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对氟碘苯 、 (3aS,5aS,9bS)-5a,9-dimethyl-3-methylene-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione 在 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以74%的产率得到(3E,3aS,5aS,9bS)-3-[(4-fluorophenyl)methylidene]-5a,9-dimethyl-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran-2,8-dione
  参考文献：
  名称：

  Semisynthetic Derivatives of Sesquiterpene Lactones by Palladium-Catalyzed Arylation of the α-Methylene-γ-lactone Substructure

  摘要：

  The palladiurn-catalyzed arylation of different alpha-methylene-gamma-lactone-containing sesquiterpene lactones was shown to produce E-olefin coupling products selectively in moderate to excellent yields. Biological evaluation of these semisynthetic sesquiterpene lactone derivatives in HeLa cells showed interesting antiproliferative profiles and provided initial structure-activity data.

  DOI：

  10.1021/jo901533e

文献信息

• Semisynthetic Derivatives of Sesquiterpene Lactones by Palladium-Catalyzed Arylation of the α-Methylene-γ-lactone Substructure
  作者：Changho Han、Francis J. Barrios、Mark V. Riofski、David A. Colby

  DOI：10.1021/jo901533e

  日期：2009.9.18

  The palladiurn-catalyzed arylation of different alpha-methylene-gamma-lactone-containing sesquiterpene lactones was shown to produce E-olefin coupling products selectively in moderate to excellent yields. Biological evaluation of these semisynthetic sesquiterpene lactone derivatives in HeLa cells showed interesting antiproliferative profiles and provided initial structure-activity data.