(-)-drim-7-ene-9α,11,12-triol | 85202-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-drim-7-ene-9α,11,12-triol
• 英文别名: 7-drimene-9α,11,12-triol；7-drimen-9α,11,12-triol；(1S,4aS,8aS)-1,2-bis(hydroxymethyl)-5,5,8a-trimethyl-4a,6,7,8-tetrahydro-4H-naphthalen-1-ol
• CAS: 85202-02-4
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: PZNQIKQMJNHKBD-AEGPPILISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-drim-7-ene-9α,11,12-triol 在 二甲基亚砜 、 三氟乙酸酐 作用下， 以64%的产率得到warburganal
  参考文献：
  名称：

  (-)-WARBURGANAL 的新型部分合成

  摘要：

  描述了从 (+)-confertifoline 到 α-环氧化物的 (-)-Warburganal 的简短合成。

  DOI：

  10.1246/cl.1985.1113
• 作为产物：
  描述：

  (-)-补身醇 在 吡啶 、 甲醇 、 氢氧化钾 、 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 (-)-drim-7-ene-9α,11,12-triol
  参考文献：
  名称：

  Oyarzun, M. L.; Cortes, M.; Sierra, J., Synthetic Communications, 1982, vol. 12, # 12, p. 951 - 958

  摘要：

  DOI：

文献信息

• Terpenoid precursors via steroid degradation: synthesis of (–)-warburganal
  作者：Sukumar Manna、Pendri Yadagiri、J. R. Falck

  DOI：10.1039/c39870001324

  日期：——

  The sesquiterpene (–)-warburganal was prepared from a (1S)-1-methoxycarbonyl-2,5,5,8a-tetramethyl-decahydronaphthalene (4) obtained by degradation of commercial glycyrrhetinic acid.

  倍半萜烯（-）-warburganal是由（1S）-1-甲氧基羰基-2,5,5,8a-四甲基-十氢化萘（4）制备的，该萘酚是通过商业甘草次酸的降解而制得的。
• Chemistry of zamoranic acid. Part IX homochiral synthesis of polygodial and warburganal from 17-acetoxy-7-labden-15-ol
  作者：Julio G. Urones、Isidro S. Marcos、Belen Gómez Pérez、Anna M. Lithgow、David Díez Patricio M. Gómez、Pilar Basabe、Narciso M. Garrido

  DOI：10.1016/0040-4020(94)01061-4

  日期：1995.2

  14,15-dinor-17-acetoxy-7-labden-13-one, 4 was prepared from zamoranic acid methyl ester 5. Photochemical cleavage of 4 gave 12-acetoxy-7,9(11)-drimadiene, 3, in 75% overall yield. The chemo- and diastereoselective epoxidation of 3 afforded 12-acetoxy-9α and 9β(11)-epoxy-7-drimene, 17 and 18 in 4:1 ratio. Ring-opening of 17 (or the mixture ) using BF3·Et2O or ring-opening of the mixture lead to the

  14,15-二也不-17-乙酰氧基-7- labden-13酮，4是从zamoranic酸甲酯制备5。光化学裂解4得到12-乙酰氧基-7,9（11）-双嘧二烯3，总产率为75％。的化疗和非对映选择性环氧化3，得到12乙酰氧基9α和9β（11） -环氧-7- drimene，17和18在4：1倍的比例。开环的17（或混合物使用BF）3 ·的Et 2 O或的混合物开环导致polygodial的合成前体：（9 - [R）-12-乙酰氧基drimen -11-人，20，非对映异构体过量90％。二烯3的化学和非对映选择性顺式羟基化反应产生了Warburganal9α，11,12-trihydroxy-7-drimene的合成前体29，收率47％。杂多醛和华宝醛分别由氮杂酸酯酸甲酯制备，总收率分别为55％和27％。
• Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum
  作者：Nicole Cortez、Víctor Marín、Verónica A. Jiménez、Víctor Silva、Oscar Leyton、Jaime R. Cabrera-Pardo、Bernd Schmidt、Matthias Heydenreich、Viviana Burgos、Paola Duran、Cristian Paz

  DOI：10.3390/ijms232112995

  日期：——

  specific compounds with chemical functionality in regions of the carbon skeleton that are not easily activated by conventional organic chemistry methods. In this work, Cladosporium antarcticum isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against Candida yeast from drimendiol and epidrimendiol. These compounds were produced

  真菌生物转化是一种有吸引力的合成策略，可在碳骨架区域产生具有化学功能的高度特异性化合物，而这些区域不易被传统有机化学方法激活。在这项工作中，Cladosporium antarcticum从南极洲柯林斯冰川的沉积物中分离出来，用于从 drimendiol 和 epidrimendiol中获得具有抗念珠菌活性的新型 drimane 倍半萜醇。这些化合物是通过在甲醇中用 NaBH 4高产率还原何首乌二醛和isotadeonal制备的。Cladosporium antarcticum从 drimendiol 中产生两种主要产物，确定为 9α-hydroxydrimendiol ( 1, 41.4 mg, 19.4% 产率) 和 3β-hydroxydrimendiol ( 2 , 74.8 mg, 35% 产率)，而表二醇的生物转化仅产生一种产物，9β-hydroxyepidrimendiol (
• 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.
• 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.