3-羟基-2-甲氧基黄烷酮 | 1050685-79-4

• 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: 3-羟基-2-甲氧基黄烷酮
• 英文名称: 3-hydroxy-2-methoxyflavanone
• 英文别名: Methoxy dihydroflavonol；3-hydroxy-2-methoxy-2-phenyl-3H-chromen-4-one
• CAS: 1050685-79-4
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: UQHGHGVNVSRNIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-羟基-2-甲氧基黄烷酮 、 乙酸酐 在 吡啶 作用下， 生成 rac-trans-3-acetoxy-2-methoxyflavanone 、 rac-cis-3-acetoxy-2-methoxyflavanone
  参考文献：
  名称：

  Obtaining new flavanones exhibiting antifungal activities by methyltrioxorhenium-catalyzed epoxidation–methanolysis of flavones

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.05.101
• 作为产物：
  描述：

  甲醇 、 黄酮 在 urea-hydrogen peroxide 、 甲基三氧化铼(VII) 作用下， 以62%的产率得到3-羟基-2-甲氧基黄烷酮
  参考文献：
  名称：

  Obtaining new flavanones exhibiting antifungal activities by methyltrioxorhenium-catalyzed epoxidation–methanolysis of flavones

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.05.101

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.