4,4-dimethyl-cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 4,4-dimethyl-cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2-one
• 英文别名: (1aS,2aR,5aS,6aR)-3,3-dimethyl-1a,2,2a,5a,6,6a-hexahydrooxireno[2,3-f][2]benzofuran-5-one
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: SZBONFDNEYPDHO-OSMVPFSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4,4-dimethyl-cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2-one
  参考文献：
  名称：

  Fungistatic Activity of Bicyclo[4.3.0]-γ-lactones

  摘要：

  Five optically active and sixteen racemic lactones (nine of them new) of bicyclo[4.3.0]nonane structure were synthesized. IC50 values for the following phytopathogens were determined: Aspergillus ochraceus AM 456, Fusarium culmorum AM 282, Fusarium oxysporum AM 13, Fusarium tricinctum AM 16. Effect of compound structures, especially stereogenic centers, on fungistatic activity has been discussed. The highest fungistatic activity was observed for trans-7,8-dibromo-cis-3-oxabicyclo-[4.3.0]nonan-2-one (3c), IC50 = 30.1 mu g/mL (0.10 mu M/mL), and cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2-one (3b), IC50 = 72.2 mu g/mL (0.47 mu M/mL), toward F. oxysporum AM 13.

  DOI：

  10.1021/jf105019u

文献信息

• Fungistatic Activity of Bicyclo[4.3.0]-γ-lactones
  作者：Teresa Olejniczak、Filip Boratyński、Agata Białońska

  DOI：10.1021/jf105019u

  日期：2011.6.8

  Five optically active and sixteen racemic lactones (nine of them new) of bicyclo[4.3.0]nonane structure were synthesized. IC50 values for the following phytopathogens were determined: Aspergillus ochraceus AM 456, Fusarium culmorum AM 282, Fusarium oxysporum AM 13, Fusarium tricinctum AM 16. Effect of compound structures, especially stereogenic centers, on fungistatic activity has been discussed. The highest fungistatic activity was observed for trans-7,8-dibromo-cis-3-oxabicyclo-[4.3.0]nonan-2-one (3c), IC50 = 30.1 mu g/mL (0.10 mu M/mL), and cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2-one (3b), IC50 = 72.2 mu g/mL (0.47 mu M/mL), toward F. oxysporum AM 13.