(3R,3aR,7S,7aS)-3-(furan-3-yl)-3a,7-dimethyl-3,4,5,6,7,7a-hexahydro-2-benzofuran-1-one | 1179343-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: (3R,3aR,7S,7aS)-3-(furan-3-yl)-3a,7-dimethyl-3,4,5,6,7,7a-hexahydro-2-benzofuran-1-one
• CAS: 1179343-59-9
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: VUEORPWXODUKMN-WSXWTOPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  梣酮 在 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 以29%的产率得到(3R,3aR,7S,7aS)-3-(furan-3-yl)-3a,7-dimethyl-3,4,5,6,7,7a-hexahydro-2-benzofuran-1-one
  参考文献：
  名称：

  Semisynthesis and Insecticidal Activity of Some Fraxinellone Derivatives Modified in the B Ring

  摘要：

  A series of novel fraxinellone derivatives modified at the C-1 or C-8 position in the B ring were prepared as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata Walker at 1 mg/mL. Five key steric configurations of compounds 2, 3, and 8f,g,j were further determined by single-crystal X-ray diffraction. It was found that the kinds and the amount of the reduction products of fraxinellone were related to the molar ratio between the reduction agent Red-Al and the substrate fraxinellone. Among all of the derivatives, compounds 2 and 8i,j,o displayed more promising insecticidal activity than their precursors fraxinellone and toosendanin. The preliminary structure-activity relationships revealed that the lactone (B-ring) of fraxinellone contributed to the observed insecticidal activity; the double bond at the C-2 position of fraxinellone was not necessary for the insecticidal activity; conversion of the oxygen atom of carbonyl group on the lactone of fraxinellone to a sulfur one does not improve the insecticidal activity; introduction of electron-withdrawing groups on the phenyl ring of 8f, to the benzoyloxy series, could result in more potent compounds.

  DOI：

  10.1021/jf404195m

文献信息

• Semisynthesis and Insecticidal Activity of Some Fraxinellone Derivatives Modified in the B Ring
  作者：Yong Guo、Huan Qu、Xiaoyan Zhi、Xiang Yu、Chun Yang、Hui Xu

  DOI：10.1021/jf404195m

  日期：2013.12.11

  A series of novel fraxinellone derivatives modified at the C-1 or C-8 position in the B ring were prepared as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata Walker at 1 mg/mL. Five key steric configurations of compounds 2, 3, and 8f,g,j were further determined by single-crystal X-ray diffraction. It was found that the kinds and the amount of the reduction products of fraxinellone were related to the molar ratio between the reduction agent Red-Al and the substrate fraxinellone. Among all of the derivatives, compounds 2 and 8i,j,o displayed more promising insecticidal activity than their precursors fraxinellone and toosendanin. The preliminary structure-activity relationships revealed that the lactone (B-ring) of fraxinellone contributed to the observed insecticidal activity; the double bond at the C-2 position of fraxinellone was not necessary for the insecticidal activity; conversion of the oxygen atom of carbonyl group on the lactone of fraxinellone to a sulfur one does not improve the insecticidal activity; introduction of electron-withdrawing groups on the phenyl ring of 8f, to the benzoyloxy series, could result in more potent compounds.