(3R,5S)-3-Hydroxy-5-((1R,4R,5S,6S,8S)-8-hydroxymethyl-4-isopropyl-1-methyl-7-methylene-bicyclo[3.2.1]oct-6-yl)-dihydro-furan-2-one

• 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: (3R,5S)-3-Hydroxy-5-((1R,4R,5S,6S,8S)-8-hydroxymethyl-4-isopropyl-1-methyl-7-methylene-bicyclo[3.2.1]oct-6-yl)-dihydro-furan-2-one
• 英文别名: (3R,5S)-3-hydroxy-5-[(1R,4R,5S,6S,8S)-8-(hydroxymethyl)-1-methyl-7-methylidene-4-propan-2-yl-6-bicyclo[3.2.1]octanyl]oxolan-2-one
• 化学式: C₁₈H₂₈O₄
• 分子量: 308.418
• InChiKey: PTGFDIFCKGMAJK-DZSLQFNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氯甲基甲基醚 在 盐酸 、 Davis' reagent 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 生成 (3R,5S)-3-Hydroxy-5-((1R,4R,5S,6S,8S)-8-hydroxymethyl-4-isopropyl-1-methyl-7-methylene-bicyclo[3.2.1]oct-6-yl)-dihydro-furan-2-one
  参考文献：
  名称：

  Synthesis of (+)-sorokinianin

  摘要：

  Sorokinianin (1), an inhibitor of barley germination, was synthesized in optically active form employing d-carvone as the only chiral source. The key steps are stereoselective intra- and intermolecular aldol reactions to construct the bicyclo[3.2.1]octane system and to introduce the lactone moiety, respectively. Our synthetic 1 showed dextrorotation and the absolute configuration of natural 1 was confirmed to be 1R,4R,5S,6R,8S,13S,2'R. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01337-3