8-羟基-5,7-二甲氧基-2-苯基色烯-4-酮 | 89971-04-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 8-羟基-5,7-二甲氧基-2-苯基色烯-4-酮
• 英文名称: 8-hydroxy-5,7-dimethoxyflavone
• 英文别名: 4H-1-Benzopyran-4-one, 8-hydroxy-5,7-dimethoxy-2-phenyl-；8-hydroxy-5,7-dimethoxy-2-phenylchromen-4-one
• CAS: 89971-04-0
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: CIAQBEKQPCMVAL-UHFFFAOYSA-N

物化性质

• 沸点：
  530.6±50.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-羟基-7-乙酰氧基黄酮 在 二甲基二环氧乙烷 、 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 4.0h， 生成 8-羟基-5,7-二甲氧基-2-苯基色烯-4-酮
  参考文献：
  名称：

  Use of acyl substituents to favour 2,3-epoxidation of 5,7-dioxygenated flavones with dimethyldioxirane

  摘要：

  The reaction of 5,7-dimethoxyflavone with dimethyldioxirane (DMDO) gives the 2,3-epoxide rapidly at first. However, low levels of ring A hydroxylated by-products are also formed. With increasing proportions of DMDO, demethylation at C-5 becomes apparent and consumption of substrate is not matched by further significant build-up of the epoxide. Deactivation of ring A by the use of acyl groups removes this complication. 5,7-Diacylflavones give excellent yields of epoxides and monoacyl derivatives also react in good yield. Ionization potential mans derived from density functional theory calculations (B3LYP/6-31G*), provide good visual indicators of the relative reactivity of the key nucleophilic loci. The epoxides may be isolated as such, or transformed into flavonols by treatment with p-toluenesulfonic acid. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.076

文献信息

• Obtaining new flavanones exhibiting antifungal activities by methyltrioxorhenium-catalyzed epoxidation–methanolysis of flavones
  作者：Roberta Bernini、Enrico Mincione、Gianfranco Provenzano、Giancarlo Fabrizi、Sabrina Tempesta、Marcella Pasqualetti

  DOI：10.1016/j.tet.2008.05.101

  日期：2008.8

  New 3-hydroxy-2-methoxyflavanones have been obtained through epoxidation-methanolysis of the corresponding flavone with urea-hydrogen peroxide (UHP)/methyltrioxorhenium (CH3ReO3, MTO) catalytic system in methanol as nucleophilic solvent. After acetylation of the reaction mixtures, the corresponding cis- and trans-3-acetoxy-2-methoxyflavanones have been isolated and characterized by spectroscopic analyses. Their antifungal activity has been tested in vitro against three fungal strains of common saprotrophic soil and seed fungi, such as Trichoderma koningii, Fusarium solani and Cladosporium herbarum, potentially pathogenic for humans. Some aspects of the structure-activity relationship of the most active compounds have been evaluated. The mycelial growth of T. koningii and C. herbarum has been totally inhibited from cis-3-acetoxy-2,6-dimethoxyflavanone 7c and cis-3-acetoxy-2,7dimethoxyflavanone 13c at the lowest concentration (0.5x10(-4) M). (C) 2008 Elsevier Ltd. All rights reserved.