o-hibiscanone | 207597-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: o-hibiscanone
• 英文别名: 3,8-Dimethyl-1,2-naphthoquinone；3,8-dimethylnaphthalene-1,2-dione
• CAS: 207597-36-2
• 化学式: C₁₂H₁₀O₂
• mdl: MFCD18447924
• 分子量: 186.21
• InChiKey: DKHAQNNRAKURNG-UHFFFAOYSA-N

物化性质

• 沸点：
  326.2±42.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(4-甲氧基-3-甲基苯基)-4-氧代丁酸 在 palladium on activated charcoal 盐酸 、 PPA 、 苯亚硒酸酐 、 三溴化硼 、 对甲苯磺酸 、 mercury(II) chloride 、 锌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 、 萘烷 、 苯 为溶剂， 反应 46.0h， 生成 o-hibiscanone
  参考文献：
  名称：

  Identification and synthesis of Trinorcadalene Phytoalexins formed by Hibiscus cannabinus in honour of Professor G. H. Neil Towers 75th birthday

  摘要：

  Two trinorcadalene phytoalexins, hibiscanal (2,8-dihydroxy-4,7-dimethoxy-6-methyl-1-naphthaldehyde) and o-hibiscanone (3,8-dimethyl-1,2-naphthoquinone), were isolated and identified from stem stele of kenaf (Hibiscus cannabinus) inoculated with the fungal pathogen Verticillium dahliae. o-Hibiscanone also was synthesized. The ED50 values of hibiscanal and o-hibiscanone against V. dahliae were 25.83 and 1.18 mu g/ml, respectively. o-Hibiscanone killed all propagules of V. dahliae and Fusarium oxysporum rtm f. sp. vasinfectum at 8 mu g/ml and 12 mu g/ml, respectively. o-Hibiscanone is more toxic to V. dahliae than desoxyhemigossypol, the most toxic phytoalexin known in cotton (Gossypium species), or mansonone C (3,8-dimethyl-5-isopropyl-1,2-naphthoquinone) which has been isolated from other malvaceous species. The implications of these findings for the genetic engineering of cotton phytoalexins is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00183-6