4-epivulgarin | 66289-87-0

• 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: 4-epivulgarin
• 英文别名: (3S,3aS,5aR,9S,9aS,9bS)-9-hydroxy-3,5a,9-trimethyl-3,3a,4,5,9a,9b-hexahydrobenzo[g][1]benzofuran-2,6-dione
• CAS: 66289-87-0
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: NGPDZEACIWDCKX-DHKWMEDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-epivulgarin 在 锌 作用下， 以 溶剂黄146 为溶剂， 生成 Deoxyvulgarin
  参考文献：
  名称：

  Eudesmanolides of Artemisia barrelieri

  摘要：

  DOI：

  10.1016/s0031-9422(00)86985-x
• 作为产物：
  描述：

  甲醇 、 [(3S,3aS,6Z,8Z,10E,11aS)-3,6,10-trimethyl-2-oxo-3a,4,5,11a-tetrahydro-3H-cyclodeca[b]furan-7-yl] acetate 在 氢氧化钾 作用下， 生成 vulgarin 、 4-epivulgarin 、 (3S,3aS,6R,9R,11aS,E)-9-methoxy-3,6,10-trimethyl-3a,4,5,6,8,9-hexahydrocyclodeca[b]furan-2,7(3H,11aH)-dione
  参考文献：
  名称：

  Partial synthesis of germacranolides with pyran and furan-type rings

  摘要：

  Pathways to synthesize germacranolides with ether bridges between C1 and C5 or C3 and C-10 were described. A joint precursor was prepared using a readily available and inexpensive compound as starting material. The key step in the preparation of dihydropyranone-germacranolides proved to be a one-pot procedure involving several transformations, induced by the iodotrimethylsilane/acetonitrile system.

  DOI：

  10.1016/s0040-4039(00)61275-3

文献信息

• Partial synthesis of germacranolides with pyran and furan-type rings
  作者：Andrés S. Hernández、María M. Afonso、Antonio G. González、Antonio Galindo

  DOI：10.1016/s0040-4039(00)61275-3

  日期：1992.8

  Pathways to synthesize germacranolides with ether bridges between C1 and C5 or C3 and C-10 were described. A joint precursor was prepared using a readily available and inexpensive compound as starting material. The key step in the preparation of dihydropyranone-germacranolides proved to be a one-pot procedure involving several transformations, induced by the iodotrimethylsilane/acetonitrile system.
• Eudesmanolides of Artemisia barrelieri
  作者：A. Villar、M.C. Zafra-Polo、M. Nicoletti、C. Galeffi

  DOI：10.1016/s0031-9422(00)86985-x

  日期：1983.1