(3S,3aS,5aS,6R,9aS,9bS)-6-(hydroxymethyl)-5a-(iodomethyl)-3-methyl-9-methylidene-3a,4,5,6,9a,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione | 313072-55-8

• 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: (3S,3aS,5aS,6R,9aS,9bS)-6-(hydroxymethyl)-5a-(iodomethyl)-3-methyl-9-methylidene-3a,4,5,6,9a,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione
• CAS: 313072-55-8
• 化学式: C₁₅H₁₉IO₅
• 分子量: 406.217
• InChiKey: ZSNZCVMPKGQXTP-VGEZIAPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,3aS,5aS,6R,9aS,9bS)-6-(hydroxymethyl)-5a-(iodomethyl)-3-methyl-9-methylidene-3a,4,5,6,9a,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione 在 potassium selenocyanate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 47.0h， 生成 (3S,3aS,5aR,9aS,9bS)-3-methyl-9-methylene-5a-vinyldecahydrofuro<2,3-f><2>benzopyran-2,8-dione
  参考文献：
  名称：

  Synthesis of (+)-8-Deoxyvernolepin and Its 11,13-Dihydroderivative. A Novel Reaction Initiated by Sulfene Elimination Leads to the 2-Oxa-cis-decalin Skeleton

  摘要：

  The title compounds are interesting candidates for antifungal screening. This paper describes the enantiospecific synthesis of these compounds starting from (+)-costunolide isolated from a commercially available extract. We used two novel reactions as key synthetic steps in this work: the acid-induced cyclization of an delta,epsilon-epoxy ester, which stereoselectively gave a hydroxymethyl-substituted delta-lactone, with the hydroxyalkyl group in the desired beta-equatorial disposition, and a reaction cascade, initiated by a base-promoted sulfene elimination, which led to a 10-oxiranyl-2-oxa-cis-decalin from the mesylate of a trans-fused delta-lactone. We also found that the reaction between selenium dioxide and the 1,5-diene system of elemanolides gave selenadecalins analogous to natural eudesmanolides. Our results prove that the synthetic strategy employed, on the basis of biomimetic concepts, is a useful procedure for the enantiospecific preparation of (+)-vernolepin-related compounds from accessible germacrolides.

  DOI：

  10.1021/jo0256538
• 作为产物：
  描述：

  (3S,3aS,5aR,6R,9aR,9bS)-6-(hydroxymethyl)-3,5a-dimethyl-9-methylidene-3a,4,5,6,9a,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione 在 碘 、 mercury(II) oxide 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 8.0h， 以49%的产率得到(3S,3aS,5aS,6R,9aS,9bS)-6-(hydroxymethyl)-5a-(iodomethyl)-3-methyl-9-methylidene-3a,4,5,6,9a,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione
  参考文献：
  名称：

  合成（+）-藜芦醇相关化合物的新策略：不寻常的亚砜消除导致2-氧杂-顺式-萘烷骨架

  摘要：

  为（+）合成的新策略- vernolepin（1），（+） - vernodalin（2），和（+） - 8- deoxyvernolepin（3）中，从访问germacrolides（+） - salonitenolide（4）和（+）-木香内酯（5）已开发出来。合成中的关键步骤是从胚芽烯到榄香烯骨架的Cope重排，环氧酯中反式δ-内酯的环化以及不寻常的亚砜消除，这会促进反应级联反应生成2-oxa -顺式-萘烷骨架。

  DOI：

  10.1016/s0040-4039(00)01334-4