(1S,2S,5R,8S)-1-methyl-4,4,8-tri(oxymethyl)tricycle[6.2.1.02,5]-undecane | 1441321-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,5R,8S)-1-methyl-4,4,8-tri(oxymethyl)tricycle[6.2.1.02,5]-undecane
• 英文别名: [(1S,2S,5R,8S)-4,4-bis(hydroxymethyl)-1-methyl-8-tricyclo[6.2.1.02,5]undecanyl]methanol
• CAS: 1441321-95-4
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: YETRFWFQVYXCLI-RFGFWPKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  石竹素 在 sodium tetrahydroborate 、 硫酸 、 四氰基乙烯 、 lithium bromide 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 216.0h， 生成 (1S,2S,5R,6S,8S)-8-hydroxymethyl-1,4,4-trimethyltricyclo[6.2.1.02,5]-undecane-6-ol 、 (1S,2S,4R,5R,6S,8S)-4,8-bis(hydroxymethyl)-1,4-dimethyltricycle-[6.2.1.02,5]undecane-6-ol 、 (1S,2S,5R,8S)-1-methyl-4,4,8-tri(oxymethyl)tricycle[6.2.1.02,5]-undecane
  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