7-methoxy-4,4-dimethyl-3H,4H-furo[3,2-c]chromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-methoxy-4,4-dimethyl-3H,4H-furo[3,2-c]chromen-2-one
• 英文别名: 7-methoxy-4,4-dimethyl-3H-furo[3,2-c]chromen-2-one
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: BCABSKNNDSWVRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-methoxy-2,2-dimethylchroman-3-one 在 氢氧化钾 、 甲基锂 、 碘 、 碳酸氢钠 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 3.25h， 生成 7-methoxy-4,4-dimethyl-3H,4H-furo[3,2-c]chromen-2-one
  参考文献：
  名称：

  Synthesis and Insect Antifeedant Activity of Precocene Derivatives with Lactone Moiety

  摘要：

  Starting from precocenes I and II, four of their derivatives with a lactone moiety were obtained. The compounds have been assessed as antifeedants against several diverse insect species including the storage pests the confused flour beetle (Tribolium confusum Duv., larvae and adults), the granary weevil beetle (Sitophilus granarius L., adults), and the khapra beetle (Trogoderma granarium Ev., larvae) and against the herbivorous pest insects Colorado potato beetle (Leptinotarsa decemlineata Say, adults and larvae) and aphids (Myzus persicae Sulz.). Precocenes, especially precocene II, showed a very strong antifeedant effect against all storage pests and aphids. The introduction of a lactone moiety caused a decrease in antifeedant activity against these species. Both precocenes were moderately active against L. decemlineata adults. The best antifeedants to this species were precocene derivatives, especially iodolactones. The introduction of iodine into a molecule had a great effect on the antifeedant activity of those compounds.

  DOI：

  10.1021/jf058034j

文献信息

• Synthesis and Insect Antifeedant Activity of Precocene Derivatives with Lactone Moiety
  作者：Maryla Szczepanik、Robert Obara、Antoni Szumny、Beata Gabryś、Aleksandra Halarewicz-Pacan、Jan Nawrot、Czesław Wawrzeńczyk

  DOI：10.1021/jf058034j

  日期：2005.7.1

  Starting from precocenes I and II, four of their derivatives with a lactone moiety were obtained. The compounds have been assessed as antifeedants against several diverse insect species including the storage pests the confused flour beetle (Tribolium confusum Duv., larvae and adults), the granary weevil beetle (Sitophilus granarius L., adults), and the khapra beetle (Trogoderma granarium Ev., larvae) and against the herbivorous pest insects Colorado potato beetle (Leptinotarsa decemlineata Say, adults and larvae) and aphids (Myzus persicae Sulz.). Precocenes, especially precocene II, showed a very strong antifeedant effect against all storage pests and aphids. The introduction of a lactone moiety caused a decrease in antifeedant activity against these species. Both precocenes were moderately active against L. decemlineata adults. The best antifeedants to this species were precocene derivatives, especially iodolactones. The introduction of iodine into a molecule had a great effect on the antifeedant activity of those compounds.