8-methoxycaryolane-5α,13β-diol | 1365002-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methoxycaryolane-5α,13β-diol
• CAS: 1365002-44-3
• 化学式: C₁₆H₂₈O₃
• 分子量: 268.397
• InChiKey: QERSSDBPJJUFQY-NXNLJZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  caryophylladienol II 在 Rhizopus stolonifer 作用下， 以 丙酮 为溶剂， 反应 144.0h， 以2.1%的产率得到8-methoxycaryolane-5α,13β-diol
  参考文献：
  名称：

  Biotransformation of 5α-hydroxycaryophylla-4(12),8(13)-diene withCunninghamella elegansandRhizopus stolonifer

  摘要：

  Biotransformation of 5 a -hydroxycaryophylla-4(12),8(13)-diene (1) was studied with Cunninghamella elegans and Rhizopus stolonifer. Incubation of 1 with C. elegans gave regioselective oxidative addition (hydration) and isomerization at the C-4(12) exocyclic double bond and hydroxylation at C-3 and C-15, and thus provided two polar metabolites, (3Z),8(14)-caryophylladiene-5 alpha,(11R)-15-diol (2) and 3 beta,4 beta,5 alpha-trihydroxycaryophylla-8(13)-ene (3). Incubation of 1 with R. stolonifer gave a transannular cyclization reaction and afforded 2 beta-methoxyclovan-9-one (4), clovan-2 beta-ol-9-one (5) and 8-methoxycaryolane-5 alpha,13 beta-diol (6). Compounds 3 and 6 are new compounds described here for the first time; their structures were deduced with the help of different spectroscopic techniques.

  DOI：

  10.3109/10242422.2011.591927