[(5aS,9aS,9bR)-1,5a,6,7,8,9,9a,9b-octahydro-6,6,9atrimethylnaphtho[2,1-c]furan-3(5H)-one] | 28400-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: [(5aS,9aS,9bR)-1,5a,6,7,8,9,9a,9b-octahydro-6,6,9atrimethylnaphtho[2,1-c]furan-3(5H)-one]
• 英文别名: (5aS,9aS,9bR)-1,5a,6,7,8,9,9a,9b-octahydro-6,6,9a-trimethylnaphtho[2,1-c]furan-3(5H)-one；(-)-cinnamolide；cinnamolide；Drim-7-en-12.11-olid；(5aS,9aS,9bR)-6,6,9a-trimethyl-5,5a,7,8,9,9b-hexahydro-1H-benzo[e][2]benzofuran-3-one
• CAS: 28400-16-0；23599-47-5
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: UMUMRNRVJNFLPT-SLEUVZQESA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  363.9±11.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(5aS,9aS,9bR)-1,5a,6,7,8,9,9a,9b-octahydro-6,6,9atrimethylnaphtho[2,1-c]furan-3(5H)-one] 在 platinum(IV) oxide 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以72%的产率得到cis-(-)-dihydrocinnamolide
  参考文献：
  名称：

  Probing the Structure–Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification

  摘要：

  The current study represents the first comprehensive investigation into the general antifouling activities of the natural drimane sesquiterpene polygodial. Previous studies have highlighted a high antifouling effect toward macrofoulers, such as ascidians, tubeworms, and mussels, but no reports about the general antifouling effect of polygodial have been communicated before. To probe the structural and chemical basis for antifouling activity, a library of 11 polygodial analogues was prepared by semisynthesis. The library was designed to yield derivatives with ranging polarities and the ability to engage in both covalent and noncovalent interactions, while still remaining within the drimane sesquiterpene scaffold. The prepared compounds were screened against 14 relevant marine micro- and macrofouling species. Several of the polygodial analogues displayed inhibitory activities at sub-microgram/mL concentrations. These antifouling effects were most pronounced against the macrofouling ascidian Ciona savignyi and the barnacle Balanus improvisus, with inhibitory activities observed for selected compounds comparable or superior to several commercial antifouling products. The inhibitory activity against the microfouling bacteria and microalgae was reversible and significantly less pronounced than for the macrofoulers. This study illustrates that the macro- and microfoulers are targeted by the compounds via different mechanisms.

  DOI：

  10.1021/acs.jnatprod.6b01056
• 作为产物：
  描述：

  drimendiol 生成 [(5aS,9aS,9bR)-1,5a,6,7,8,9,9a,9b-octahydro-6,6,9atrimethylnaphtho[2,1-c]furan-3(5H)-one]
  参考文献：
  名称：

  HE, JU-FANG;WU, YU-LIN, TETRAHEDRON, 44,(1988) N 7, 1933-1940

  摘要：

  DOI：

文献信息

• HE, JU-FANG;WU, YU-LIN, TETRAHEDRON, 44,(1988) N 7, 1933-1940
  作者：HE, JU-FANG、WU, YU-LIN

  DOI：——

  日期：——
• HE, JU-FANG;WU, YU-LIN, ORG. CHEM.,(1987) N 5, 354-356
  作者：HE, JU-FANG、WU, YU-LIN

  DOI：——

  日期：——
• Probing the Structure–Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification
  作者：Lindon W. K. Moodie、Rozenn Trepos、Gunnar Cervin、Lesley Larsen、David S. Larsen、Henrik Pavia、Claire Hellio、Patrick Cahill、Johan Svenson

  DOI：10.1021/acs.jnatprod.6b01056

  日期：2017.2.24

  The current study represents the first comprehensive investigation into the general antifouling activities of the natural drimane sesquiterpene polygodial. Previous studies have highlighted a high antifouling effect toward macrofoulers, such as ascidians, tubeworms, and mussels, but no reports about the general antifouling effect of polygodial have been communicated before. To probe the structural and chemical basis for antifouling activity, a library of 11 polygodial analogues was prepared by semisynthesis. The library was designed to yield derivatives with ranging polarities and the ability to engage in both covalent and noncovalent interactions, while still remaining within the drimane sesquiterpene scaffold. The prepared compounds were screened against 14 relevant marine micro- and macrofouling species. Several of the polygodial analogues displayed inhibitory activities at sub-microgram/mL concentrations. These antifouling effects were most pronounced against the macrofouling ascidian Ciona savignyi and the barnacle Balanus improvisus, with inhibitory activities observed for selected compounds comparable or superior to several commercial antifouling products. The inhibitory activity against the microfouling bacteria and microalgae was reversible and significantly less pronounced than for the macrofoulers. This study illustrates that the macro- and microfoulers are targeted by the compounds via different mechanisms.