(8R,9R)-isocaryolane-8,9-diol | 99805-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8R,9R)-isocaryolane-8,9-diol
• 英文别名: (1S,2S,5R,8R,9R)-1,4,4-trimethyltricyclo[6.3.1.02,5]dodecane-8,9-diol
• CAS: 99805-54-6
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: GWCBXQJXFMEEBJ-FMKNKJFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• 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：

  (8R,9R)-isocaryolane-8,9-diol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.17h， 以0.010 g的产率得到1S,2S,5R,8R-8-hydroxy-1,4,4-trimethyltricyclo<6.3.1.02,5>dodecane-9-one
  参考文献：
  名称：

  Tkachev, A. V.; Gatilov, Yu. V.; Bagryanskaya, I. Yu., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 3, p. 490 - 503

  摘要：

  DOI：
• 作为产物：
  描述：

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

  Biotransformation of Bioactive Isocaryolanes by Botrytis cinerea

  摘要：

  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.

  DOI：

  10.1021/np1009465

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。
• 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.
• Tkachev, A. V.; Gatilov, Yu. V.; Bagryanskaya, I. Yu., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 3, p. 490 - 503
  作者：Tkachev, A. V.、Gatilov, Yu. V.、Bagryanskaya, I. Yu.、Shakirov, M. M.、Mamatyuk, V. I.、et al.

  DOI：——

  日期：——
• 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.