diisophorone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diisophorone
• 英文别名: (1R,9S)-1-hydroxy-5,5,9,11,11-pentamethyltricyclo[7.3.1.02,7]tridec-2(7)-en-3-one
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: IJDSUFQMYUARCQ-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diisophorone 在 Botrytis cinerea UCA₉₉₂ 作用下， 以 乙醇 为溶剂， 反应 240.0h， 以30 mg的产率得到8β-hydroxydiisophorone
  参考文献：
  名称：

  Antifungal Activity and Biotransformation of Diisophorone by Botrytis cinerea

  摘要：

  Diisophorone (1) was tested against two strains of the necrotrophic plant pathogen Botrytis cinerea. Fungal sensitivity varied according to the strain. B. cinera 2100 was more sensitive than B. cinerea UCA992: its mycelial growth was significantly inhibited at concentrations of 50 ppm and above. Although diisophorone (1) showed an effective control of B. cinerea, a detoxification mechanism was present. The detoxification of racemic diisophorone (1) by B. cinerea was investigated. Incubation with two strains of B. cinerea gave one and four biotransformation products (2-5), respectively. Their structures were established as the known 8 beta-hydroxycliisoplhorone (2), 6 alpha-hydroxydiisophorone (3), 6 beta-hydroxydiisophorone (4) and 8 beta,14 beta-dihydroxydiisophorone (5) on the basis of their spectroscopic data, including two-dimensional NMR analysis [heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser enhancement spectroscopy (NOESY)] and an X-ray crystallographic study.

  DOI：

  10.1021/jf050600n