Aplysillolide A | 130221-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: Aplysillolide A
• 英文别名: (1S,3aR,6R,7Z,7aR)-7-ethylidene-1-hydroxy-6-[(1S)-1,3,3-trimethylcyclohexyl]-3,3a,4,7a-tetrahydro-1H-2-benzofuran-5-one
• CAS: 130221-22-6
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: RPHDRFPSWHBWIN-BVJOOIOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Aplysillolide A 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以13.2 mg的产率得到(1R,4R,5R,1'S)-6-Eth-(Z)-ylidene-4,5-bis-hydroxymethyl-1',3',3'-trimethyl-bicyclohexyl-2-ol
  参考文献：
  名称：

  Terpenoids from the sponge Aplysilla glacialis and specimens of the nudibranch Cadlina luteomarginta found on the sponge

  摘要：

  Four new rearranged and/or degraded ''spongian'' terpenoids and one new ''marginatane'' diterpenoid have been isolated from the marine sponge Aplysilla glacialis. The structure of cadlinolide A (3) was solved by X-ray diffraction analysis, and the structures of cadlinolide B (4), aplysillolide A (5), aplysillolide B (6), and marginatone (7) were determined by extensive spectroscopic analysis and chemical interconversions. Glaciolide (2), cadlinolide A (3), and tetrahydroaplysulphurin-1 (8) were isolated from skin extracts of specimens of the dorid nudibranch Cadlina luteomarginata found feeding on A. glacialis.

  DOI：

  10.1021/jo00001a010