3',4,4',5,6-pentamethoxyaurone | 927429-56-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: 3',4,4',5,6-pentamethoxyaurone
• 英文别名: (Z)-2-(3,4-dimethoxybenzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one；(2Z)-2-[(3,4-dimethoxyphenyl)methylidene]-4,5,6-trimethoxy-1-benzofuran-3-one
• CAS: 927429-56-9
• 化学式: C₂₀H₂₀O₇
• 分子量: 372.375
• InChiKey: HRVXMGXGJWDUTF-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2'-hydroxy-3,4,4',5',6'-pentamethoxychalcone 、 双氧水 以75%的产率得到
  参考文献：
  名称：

  STEFANOVIC M.; KRSTIC L.; RIHTER B.; MLADENOVIC S., J. SERB. CHEM. SOC., 52,(1987) N 1, 61-62

  摘要：

  DOI：

文献信息

• Divergent Approach to Flavones and Aurones via Dihaloacrylic Acids. Unexpected Dependence on the Halogen Atom
  作者：George A. Kraus、Vinayak Gupta

  DOI：10.1021/ol1023294

  日期：2010.11.19

  The reaction of phenols with 7a led to the synthesis of aurones, while the reaction of phenols with 7b led to the synthesis of flavones.
• Synthesis and Insect Antifeedant Activity of Aurones against <i>Spodoptera litura</i> Larvae
  作者：Masanori Morimoto、Hiromi Fukumoto、Toki Nozoe、Ai Hagiwara、Koichiro Komai

  DOI：10.1021/jf062562t

  日期：2007.2.1

  A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 mu mol/cm(2). The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3',4',5'-trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED(50)) and a hydrogen-bonding parameter calculated from the R-f value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.
• STEFANOVIC M.; KRSTIC L.; RIHTER B.; MLADENOVIC S., J. SERB. CHEM. SOC., 52,(1987) N 1, 61-62
  作者：STEFANOVIC M.、 KRSTIC L.、 RIHTER B.、 MLADENOVIC S.

  DOI：——

  日期：——