5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one
• 英文别名: 5-Hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one
• 化学式: C₇H₈O₄
• 分子量: 156.138
• InChiKey: DMSMEGJRXZJGIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4-methoxy-7-oxabicyclo[4.1.0]hept-3-en-2-one 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以9.3 mg的产率得到3-methoxy-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
  参考文献：
  名称：

  Sphaeropsidones, Phytotoxic Dimedone Methyl Ethers Produced by Diplodia cupressi: A Structure−Activity Relationship Study

  摘要：

  Sphaeropsidone and episphaeropsidone are two phystotoxic dimedone methyl ethers produced by Diplodia cupressi, the causal agent of:a canker disease of cypress in the Mediterranean area In this study, eight derivatives obtained by chemical modifications,and two natural analogues were assayed for,phytotoxic and antifungal activities, and a, structure-activity relationship was examined Each compound was tested on nonhost plants and on five fungal pathogenic :species belonging to the. genus Phytophthora. The results provide insights into structure-activity relationships within these compounds. It was found that the hydroxy group at C-5, the absolute C-5 configuration, the epoxy group, and the C-2 carbonyl croup appear to be structural features important in conferring biological activity. The conversion of sphaeropsidone into the corresponding 1,4- dione derivative led to a compound showing greater antifungal activity than its precursor. This finding could be useful in devising new natural fungicides for practical application in agriculture.,

  DOI：

  10.1021/np100837r

文献信息

• Sphaeropsidones, Phytotoxic Dimedone Methyl Ethers Produced by <i>Diplodia cupressi</i>: A Structure−Activity Relationship Study
  作者：Antonio Evidente、Lucia Maddau、Bruno Scanu、Anna Andolfi、Marco Masi、Andrea Motta、Angela Tuzi

  DOI：10.1021/np100837r

  日期：2011.4.25

  Sphaeropsidone and episphaeropsidone are two phystotoxic dimedone methyl ethers produced by Diplodia cupressi, the causal agent of:a canker disease of cypress in the Mediterranean area In this study, eight derivatives obtained by chemical modifications,and two natural analogues were assayed for,phytotoxic and antifungal activities, and a, structure-activity relationship was examined Each compound was tested on nonhost plants and on five fungal pathogenic :species belonging to the. genus Phytophthora. The results provide insights into structure-activity relationships within these compounds. It was found that the hydroxy group at C-5, the absolute C-5 configuration, the epoxy group, and the C-2 carbonyl croup appear to be structural features important in conferring biological activity. The conversion of sphaeropsidone into the corresponding 1,4- dione derivative led to a compound showing greater antifungal activity than its precursor. This finding could be useful in devising new natural fungicides for practical application in agriculture.,