8αH,9αH-11,12-drimantriol | 58698-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8αH,9αH-11,12-drimantriol
• 英文别名: drimane-11,12-diol；8β,9β-drimane-11,12-diol；[(1S,2S,4aS,8aS)-1-(hydroxymethyl)-5,5,8a-trimethyl-1,2,3,4,4a,6,7,8-octahydronaphthalen-2-yl]methanol
• CAS: 58698-99-0
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: ZDBPQFUSFKWTEM-UKTARXLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8αH,9αH-11,12-drimantriol 在 吡啶 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 36.0h， 生成 (+)-(4aS,12bS)-4,4,12b-trimethyl-1,2,3,4,4a,5,6,12b-octahydrobenzo[a]anthracene-8,11-dione
  参考文献：
  名称：

  (+)-环佐那隆的合成和天然存在的(-)-环佐那隆的绝对构型。

  摘要：

  使用(-)-蓼二醛(3)作为手性起始原料合成了(+)-环佐那隆(1)。通过与(+)-环佐酮的光谱数据和旋光度比较，确定天然存在的(-)-环佐酮的绝对构型为5R，10R。

  DOI：

  10.1021/np0004146
• 作为产物：
  描述：

  辛辣木素 在 盐酸 、 lithium aluminium tetrahydride 、 铂 作用下， 生成 8αH,9αH-11,12-drimantriol
  参考文献：
  名称：

  906.倍半萜。第二部分 drimenin，isodrimenin和confertifolin的组成和立体化学

  摘要：

  DOI：

  10.1039/jr9600004685

文献信息

• Biosynthesis of drimane terpenoids in dorid molluscs: Pivotal role of 7-deacetoxyolepupuane in two species of Dendrodoris nudibranchs
  作者：Angelo Fontana、Maria Letizia Ciavatta、Tomofumi Miyamoto、Aldo Spinella、Guido Cimino

  DOI：10.1016/s0040-4020(99)00256-2

  日期：1999.4

  Described in this paper is the biosynthesis of defensive drimanes in dorid nudibranchs. Two geographically distinct populations of molluscs belonging to the genus Dendrodoris have been studied. The de novo synthesis of 7-deacetoxyolepupuane (2) has been demonstrated by radiolabelled precursors in both species. The results of the studies are consistent with the pivotal role of 2 in the formation of

  本文描述的是多色裸枝中防御性drimanes的生物合成。研究了两个属于Dendrodoris属的地理上不同的软体动物种群。在从头7 deacetoxyolepupuane（合成2）已经通过在这两个物种放射性标记前体的证明。研究结果与2在软体动物的地幔和卵团中其他drimanes形成中的关键作用相一致。据报道，新的drimane6-β-acetoxypolygodial（7）是从太平洋Dendrodoris arborescens的皮肤提取物中得到的。其结构阐明是通过NMR光谱法完成的。
• Synthesis of 11,12-Epoxydrim-8,12-en-11-ol, 11,12-Diacetoxydrimane, and Warburganal from (−)-Sclareol
  作者：A. F. Barrero、M. Cortés、E. A. Manzaneda、E. Cabrera、R. Chahboun、M. Lara、A. R. Rivas

  DOI：10.1021/np990140q

  日期：1999.11.1

  The first syntheses are reported for recently isolated drimanes 11,12-epoxydrim-8,12-en-11-ol (2) and 11,12-diacetoxydrimane (3), from (-)-sclareol (1). Furthermore, two efficient new routes to the potent bioactive warburganal (4) starting also from 1 are described.
• CONVERSION OF (+)-CONFERTIFOLIN INTO 11,12-BISNORDRIMAN-9-ONE AND (+)-8αH,9αH-11,12-DIACETOXYDRIMANE^*
  作者：Julio Benites、Marcelo D. Preite、Manuel Cortés

  DOI：10.1081/scc-100104043

  日期：2001.1

  A short synthesis of naphthalenone (-)-1 and natural drimanic diacetate ((+)-3), from confertifolin ((+)-4), is reported. The proposed absolute configuration of(+)-3 was confirmed.
• Benites, Julio; Armstrong, Veronica; Cortes, Manuel, Journal of Chemical Research, 2006, # 10, p. 649 - 650
  作者：Benites, Julio、Armstrong, Veronica、Cortes, Manuel

  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.