(8S,9R)-isocaryolan-9-ol | 203437-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8S,9R)-isocaryolan-9-ol
• 英文别名: (1S,2S,5R,8S,9R)-1,4,4-trimethyltricyclo[6.3.1.02,5]dodecan-9-ol
• CAS: 203437-41-6
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: CGMOEAZPKYMTPK-ARUSPNSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (8S,9R)-isocaryolan-9-ol 在 B_.cinerea 作用下， 反应 120.0h， 以19 mg的产率得到(8R,9R)-isocaryolane-8,9-diol
  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
• 作为产物：
  描述：

  (8S)-isocaryolan-9-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 (8S,9R)-isocaryolan-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

• 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.