[4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] 2-phenylacetate | 1184982-21-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: [4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] 2-phenylacetate
• CAS: 1184982-21-5
• 化学式: C₂₉H₂₆O₈
• 分子量: 502.521
• InChiKey: WBQMSQCIPTYZCJ-PIVNMMCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯乙酸 、 4 ’-去甲去氧鬼臼毒素 在 4-二甲氨基吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到[4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] 2-phenylacetate
  参考文献：
  名称：

  Semisynthesis and Quantitative Structure−Activity Relationship (QSAR) Study of Novel Aromatic Esters of 4′-Demethyl-4-deoxypodophyllotoxin as Insecticidal Agents

  摘要：

  By using podophyllotoxin as a phytoinsecticidal lead compound, 15 novel aromatic esters of 4'-demethyl-4-deoxypodophyllotoxin were semisynthesized and preliminarily tested for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo for the first time. Among all of the tested compounds, especially two compounds, 4m and 4o, containing a pyridinyl group, for which final corrected mortality rates against M. separata at 1 mg/mL were 62.9 and 59.2%, respectively, showed the most promising and pronounced insecticidal activity as compared with toosendanin, a commercial insecticide derived from Melia azedarach. The quantitative structure-activity relationships (QSAR) of compounds 4a-4o showed that the relative number of benzene rings and final heat of formation were very important descriptors to their insecticidal activity.

  DOI：

  10.1021/jf9020812

文献信息

• Semisynthesis and Quantitative Structure−Activity Relationship (QSAR) Study of Novel Aromatic Esters of 4′-Demethyl-4-deoxypodophyllotoxin as Insecticidal Agents
  作者：Hui Xu、Juanjuan Wang、Huijun Sun、Min Lv、Xuan Tian、Xiaojun Yao、Xing Zhang

  DOI：10.1021/jf9020812

  日期：2009.9.9

  By using podophyllotoxin as a phytoinsecticidal lead compound, 15 novel aromatic esters of 4'-demethyl-4-deoxypodophyllotoxin were semisynthesized and preliminarily tested for their insecticidal activity against the pre-third-instar larvae of Mythimna separata Walker in vivo for the first time. Among all of the tested compounds, especially two compounds, 4m and 4o, containing a pyridinyl group, for which final corrected mortality rates against M. separata at 1 mg/mL were 62.9 and 59.2%, respectively, showed the most promising and pronounced insecticidal activity as compared with toosendanin, a commercial insecticide derived from Melia azedarach. The quantitative structure-activity relationships (QSAR) of compounds 4a-4o showed that the relative number of benzene rings and final heat of formation were very important descriptors to their insecticidal activity.