(1S,2S,4R,5R,8R,11S,12S)-5-methoxy-4,8,12-trimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradecane-7,13-dione | 144067-19-6

• 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: (1S,2S,4R,5R,8R,11S,12S)-5-methoxy-4,8,12-trimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradecane-7,13-dione
• CAS: 144067-19-6
• 化学式: C₁₆H₂₄O₅
• 分子量: 296.364
• InChiKey: PNSRFIMOLNXZSO-JLKACQGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,5R,8R,11S,12S)-5-methoxy-4,8,12-trimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradecane-7,13-dione 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以56%的产率得到(1R,2S,5S,6S,9R,13R)-5,9,13-trimethyl-3,14-dioxatricyclo[8.3.1.02,6]tetradec-10-ene-4,12-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
• 作为产物：
  描述：

  (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 在 间氯过氧苯甲酸 作用下， 以94%的产率得到(1S,2S,4R,5R,8R,11S,12S)-5-methoxy-4,8,12-trimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradecane-7,13-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.