(-)-3',4',5,7-tetramethoxyflavanone | 74628-43-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (-)-3',4',5,7-tetramethoxyflavanone
• 英文别名: (2S)-5,7,3',4'-tetramethoxyflavanone；hesperetin-5,7,3'-O-trimethylether；HTME；(S)-5,7,3',4'-tetramethoxyflavanone；(2s)-5,7,3',4'-Tetramethoxyflavanone；(2S)-2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-2,3-dihydrochromen-4-one
• CAS: 74628-43-6
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: FPXNMRFTZWGJIT-HNNXBMFYSA-N

物化性质

• 沸点：
  530.0±50.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-3',4',5,7-tetramethoxyflavanone 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以90%的产率得到3,4,5,7-四甲氧基黄酮
  参考文献：
  名称：

  Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX)

  摘要：

  2-Iodoxybenzoic acid (IBX), a mild and efficient hypervalent iodine oxidant, has been utilised in different reaction conditions to perform several efficient oxidative modifications of flavonoids. Fine-tuning of the reaction conditions allowed remarkably selective modifications of these compounds. At room temperature, IBX proved to be an excellent reagent for a highly regioselective aromatic hydroxylation of monohydroxylated flavanones and flavones, generating the corresponding catecholic derivatives showing high antioxidant activity. At 90 degrees C, IBX efficiently dehydrogenated a large panel of methoxylated flavanones to their corresponding flavones exhibiting anticancer activity. IBX polystyrene has also been utilised to increase the recovery of highly polar compounds. Following the first oxidation, the reagent was recovered and reused in several runs without loss of efficiency and selectivity. The first example of an application of IBX polystyrene in a dehydrogenation reaction has been described. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.014
• 作为产物：
  描述：

  花旗松素 在 间苯三酚 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 为溶剂， 反应 53.0h， 生成 (-)-3',4',5,7-tetramethoxyflavanone
  参考文献：
  名称：

  α-酮醇的光化学脱氧：二氢黄酮醇-黄酮酮转化

  摘要：

  在无水乙酸乙酯中辐照光学纯的2,3-反-3-羟基黄酮类化合物直接导致游离酚类黄烷酮类似物的完全保留在C（2）的配置。类似地，它们的甲基醚得到相应的黄烷酮和黄酮。该反应代表在Clemmensen条件下还原的光化学当量。

  DOI：

  10.1039/p19800001003

文献信息

• Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX)
  作者：Maurizio Barontini、Roberta Bernini、Fernanda Crisante、Giancarlo Fabrizi

  DOI：10.1016/j.tet.2010.06.014

  日期：2010.8

  2-Iodoxybenzoic acid (IBX), a mild and efficient hypervalent iodine oxidant, has been utilised in different reaction conditions to perform several efficient oxidative modifications of flavonoids. Fine-tuning of the reaction conditions allowed remarkably selective modifications of these compounds. At room temperature, IBX proved to be an excellent reagent for a highly regioselective aromatic hydroxylation of monohydroxylated flavanones and flavones, generating the corresponding catecholic derivatives showing high antioxidant activity. At 90 degrees C, IBX efficiently dehydrogenated a large panel of methoxylated flavanones to their corresponding flavones exhibiting anticancer activity. IBX polystyrene has also been utilised to increase the recovery of highly polar compounds. Following the first oxidation, the reagent was recovered and reused in several runs without loss of efficiency and selectivity. The first example of an application of IBX polystyrene in a dehydrogenation reaction has been described. (c) 2010 Elsevier Ltd. All rights reserved.
• Photochemical deoxygenation of an α-ketol: the dihydroflavonol–flavanone conversion
  作者：Jan H. van der Westhuizen、Daneel Ferreira、David G. Roux

  DOI：10.1039/p19800001003

  日期：——

  to free phenolic flavanone analogues with complete retention of configuration at C(2). Similarly their methyl ethers give the corresponding flavanones and flavones. The reaction represents the photochemical equivalent of a reduction under Clemmensen conditions.

  在无水乙酸乙酯中辐照光学纯的2,3-反-3-羟基黄酮类化合物直接导致游离酚类黄烷酮类似物的完全保留在C（2）的配置。类似地，它们的甲基醚得到相应的黄烷酮和黄酮。该反应代表在Clemmensen条件下还原的光化学当量。