(8R,9R)-8-methoxyisocaryolan-9-ol | 248918-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8R,9R)-8-methoxyisocaryolan-9-ol
• 英文别名: (1S,2S,5R,8R,9R)-8-methoxy-1,4,4-trimethyltricyclo[6.3.1.02,5]dodecan-9-ol
• CAS: 248918-61-8
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: SSEZFAIKOUPCOF-HDNYOTOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8R,9R)-8-methoxyisocaryolan-9-ol 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 (1S,2S,5R,8S,9R)-1,4,4-trimethyltricyclo[7.2.1.0^2,5]dodecan-8-ol
  参考文献：
  名称：

  Novel methoxyl and hydroxyl directed pinacol rearrangements of an isocaryolane sesquiterpenoid under Mitsunobu conditions

  摘要：

  Treatment of 8-methoxy-isocaryolan-9 alpha-ol (1) with acid on the one hand and with diethyl azodicarboxylate (DEAD)/triphenylphosphine on the other, leads to different pinacol rearrangements of the isocaryolane skeleton. 1S,2S,5R,9R-8-oxo-1,4,4-trimethyltricyclo[7.2.1.0(2,5)]dodecane (2), which possesses a novel sesquiterpenoid skeleton, was obtained under Mitsunobu conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01335-0
• 作为产物：
  描述：

  石竹素 在 四氰基乙烯 、 lithium bromide 作用下， 以 丙酮 为溶剂， 生成 (8R,9R)-8-methoxyisocaryolan-9-ol
  参考文献：
  名称：

  Phytotoxic Activity and Metabolism of Botrytis cinerea and Structure–Activity Relationships of Isocaryolane Derivatives

  摘要：

  Research has been conducted on the biotransformation Of (8S,9R)-isocaryolan-9-ol (4a) and (1S,2S,5R,8S)-8-methylene-1,4,4-trimethyltricyclo [6.2.1.0(2'5)] uridecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4a yielded compounds 6-9, while the biotransformation of compound 5a yielded compounds 10-13. The activity of compounds 4a and 5a against B. cinerea has been evaluated. (8R,9R)- Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3,4a, and 5a, together with. their biotransformation products 6-8, 10, and 14-17, on the germination and radicle and shoot growth of Lactuca sativa (lettuce) has also been determined. Compounds 7-13 are, described for the first time.

  DOI：

  10.1021/np3009013

文献信息

• Novel Rearrangement of an Isocaryolane Sesquiterpenoid under Mitsunobu Conditions
  作者：Juan C. Racero、Antonio J. Macías-Sánchez、Rosario Hernández-Galán、Peter B. Hitchcock、James R. Hanson、Isidro G. Collado

  DOI：10.1021/jo000765p

  日期：2000.11.1

  Under modified Mitsunobu reaction conditions, a novel skeleton rearrangement of terpenes has been obtained. The reactivity of 8, 9-dioxygenated isocaryolane derivatives has been investigated. When either (8R,9R)-8-methoxyisocaryolane-9-ol (7) or (8R, 9R)-isocaryolane-8,9-diol (10) are treated under acidic conditions, isocaryolan-9-one (9) and the rearrangement compound (1S,2S,5R,8S)-1, 4,4-trimethyltricyclo[6

  在改良的Mitsunobu反应条件下，获得了萜烯的新型骨架重排。已经研究了8、9-二加氧异芳烷衍生物的反应性。当在酸性条件下处理（8R，9R）-8-甲氧基异芳烷-9-ol（7）或（8R，9R）-异芳烷-8,9-二醇（10）时，异方烷-9-一（9）和得到重排化合物（1S，2S，5R，8S）-1，4,4-三甲基三环[6.2.1.0（2,5）]十一烷-8-甲醛（11）。否则，在改良的Mitsunobu条件下处理化合物7和10会导致产生新的倍半萜衍生物（1S，2S，5R，9R）-1,4,4-三甲基三环[7.2.1.0（2,5）] dodecan-8-one（ 8）。据我们所知，这是由Mitsunobu引起的频哪醇重排的第一个例子。都探讨了底物和反应条件对反应进行的影响。
• New trifluoromethylated sesquiterpenoids: synthesis, rearrangement, and biological activity
  作者：Yulia V. Gyrdymova、Roman V. Rumyantcev、Yana L. Esaulkova、Svetlana V. Belyaevskaya、Vladimir V. Zarubaev、Airat R. Kayumov、Svetlana A. Rubtsova

  DOI：10.1039/d2nj04611c

  日期：——

  substances. However, the synthesis of fluorine-containing compounds having a complicated structure using classical synthetic methods is often problematic. In this work, we demonstrated the capacity of the isomerization reaction as an efficient and atom-economical tool for the synthesis of complex compounds using the natural sesquiterpenoid caryophyllene oxide as an example. The rearrangement pathways of 8-trifluoromethyl-4

  三氟甲基化化合物是重要的药物物质。然而，使用经典合成方法合成具有复杂结构的含氟化合物往往存在问题。在这项工作中，我们以天然倍半萜类石竹烯氧化物为例，展示了异构化反应作为一种高效且原子经济的工具合成复杂化合物的能力。已经提出了 8-trifluoromethyl-4,5-epoxycaryophyllanyl-8-ol 的重排途径。合成的倍半萜类化合物被证明具有作为具有抗病毒和抗菌特性的生物活性化合物的巨大潜力。
• Biotransformation of Bioactive Isocaryolanes by <i>Botrytis cinerea</i>
  作者：Jociani Ascari、Maria Amélia Diamantino Boaventura、Jacqueline Aparecida Takahashi、Rosa Durán-Patrón、Rosario Hernández-Galán、Antonio J. Macías-Sánchez、Isidro G. Collado

  DOI：10.1021/np1009465

  日期：2011.8.26

  The metabolism of the fungistatic agent (8R,9R)-8-methoxyisocaryolan-9-ol (4) by the fungus Botrytis cinerea has been investigated. Biotransformation of compound 4 yielded compounds 5 and 6-9. No dihydrobotrydial is observed after 4 days of incubation of compound 4. Separate biotransformation of (8R,9R)-isocaryolane-8,9-diol (5) yielded compounds 7-11. The evaluation of the fungistatic activity against B. cinerea of compounds 4, 5, and 6 is reported. (4R,8R,9R)-8-Methoxyisocaryolane-9,15-diol (6), a major metabolite of (8R,9R)-8-methoxyisocaryolan-9-ol (4), shows a much reduced biological activity when compared with the parent compound. Isocaryolane derivatives 6-11 are described for the first time.
• Phytotoxic Activity and Metabolism of <i>Botrytis cinerea</i> and Structure–Activity Relationships of Isocaryolane Derivatives
  作者：Jociani Ascari、Maria Amélia Diamantino Boaventura、Jacqueline Aparecida Takahashi、Rosa Durán-Patrón、Rosario Hernández-Galán、Antonio J. Macías-Sánchez、Isidro G. Collado

  DOI：10.1021/np3009013

  日期：2013.6.28

  Research has been conducted on the biotransformation Of (8S,9R)-isocaryolan-9-ol (4a) and (1S,2S,5R,8S)-8-methylene-1,4,4-trimethyltricyclo [6.2.1.0(2'5)] uridecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4a yielded compounds 6-9, while the biotransformation of compound 5a yielded compounds 10-13. The activity of compounds 4a and 5a against B. cinerea has been evaluated. (8R,9R)- Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3,4a, and 5a, together with. their biotransformation products 6-8, 10, and 14-17, on the germination and radicle and shoot growth of Lactuca sativa (lettuce) has also been determined. Compounds 7-13 are, described for the first time.
• Novel methoxyl and hydroxyl directed pinacol rearrangements of an isocaryolane sesquiterpenoid under Mitsunobu conditions
  作者：Isidro G. Collado、James R. Hanson、Rosario Hernández-Galán、Peter B. Hitchcock、Antonio J. Macías-Sánchez、Juan C. Racero

  DOI：10.1016/s0040-4039(99)01335-0

  日期：1999.8

  Treatment of 8-methoxy-isocaryolan-9 alpha-ol (1) with acid on the one hand and with diethyl azodicarboxylate (DEAD)/triphenylphosphine on the other, leads to different pinacol rearrangements of the isocaryolane skeleton. 1S,2S,5R,9R-8-oxo-1,4,4-trimethyltricyclo[7.2.1.0(2,5)]dodecane (2), which possesses a novel sesquiterpenoid skeleton, was obtained under Mitsunobu conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.