(+)-3',4',7-tri-O-methyldihydroquercetin | 74628-44-7

• 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',7-tri-O-methyldihydroquercetin
• 英文别名: (+)-7,3',4'-tri-O-methyltaxifolin；7,3′,4′-O-trimethyltaxifolin；(2R,3R)-2-(3,4-dimethoxyphenyl)-3,5-dihydroxy-7-methoxy-2,3-dihydrochromen-4-one
• CAS: 74628-44-7
• 化学式: C₁₈H₁₈O₇
• 分子量: 346.337
• InChiKey: HIGBPIRRWMYOGC-ZWKOTPCHSA-N

物化性质

• 沸点：
  590.7±50.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+)-3',4',7-tri-O-methyldihydroquercetin 在 二苯甲酮 、 间苯三酚 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以2%的产率得到7,3',4'-三-O-甲基毛地黄黄酮
  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
• 作为产物：
  描述：

  (2R,3R)-2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-bis[[(3R,4S,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]-2,3-dihydrochromen-4-one 生成 (+)-3',4',7-tri-O-methyldihydroquercetin
  参考文献：
  名称：

  AGNIHOTRI, V. K.;SRIVASTAVA, S. D.;SRIVASTAVA, S. K.;PIIRE, S.;RUSIA, K., INDIAN J. PHARM. SCI., 49,(1987) N 2, 66-69

  摘要：

  DOI：

文献信息

• Leucocyanidin: Synthesis and properties of (2R,3S,4R)-(+)-3,4,5,7,3′,4′-hexahydroxyflavan
  作者：Lawrence J. Porter、L.Yeap Foo

  DOI：10.1016/0031-9422(80)85075-8

  日期：1980.1

  Abstract An isomer of leucocyanidin, (2 R ,3 S ,4 R )-(+)-3,4,5,7,3′,4′-hexahydroxyflavan has been synthesized from (+)-taxifolin, isolated in its phe

  摘要 从 (+)-紫杉叶素中分离出一种无色花青素异构体 (2 R ,3 S ,4 R )-(+)-3,4,5,7,3',4'-六羟基黄烷
• Structure–Activity Relationship for (+)-Taxifolin Isolated from Silymarin as an Inhibitor of Amyloid β Aggregation
  作者：Mizuho SATO、Kazuma MURAKAMI、Mayumi UNO、Haruko IKUBO、Yu NAKAGAWA、Sumie KATAYAMA、Ken-ichi AKAGI、Kazuhiro IRIE

  DOI：10.1271/bbb.120925

  日期：2013.5.23

  Silymarin, the seed extract of Silybium marianum, has preventive effects against Alzheimer's disease-like pathogenesis in vivo. We isolated (+)-taxifolin (4) from silymarin as an inhibitor of aggregation of the 42-residue amyloid beta-protein. Structure-activity relationship studies revealed the 3',4'-dihydroxyl groups to be critical to the anti-aggregative ability, whereas the 7-hydroxyl group and the stereochemistry at positions 2 and 3 were not important.
• Methylation of Dihydroquercetin Acetates:  Synthesis of 5-<i>O</i>-Methyldihydroquercetin
  作者：Eberhard Kiehlmann、Peter W. Slade

  DOI：10.1021/np034005w

  日期：2003.12.1

  The major products of methylation of dihydroquercetin (1, dhq) with diazomethane have been identified as 7-O-methyldhq (9), 7,3'-di-0-methyldhq (10), 7,4'-di-O-methyldhq (11), and 7,3',4'-tri-O-methyldhq (2). With dhq 3,7,3',4'-tetraacetate (6), dhq 3,5,3',4'-tetraacetate (5), dhq 3,3',4'-triacetate (7), dhq 7,3',4'triacetate (8), and dhq 3-acetate (4) the same reaction affords mainly 5-O-methyldhq 3,7,3',4'-tetraacetate (15), 7-O-methyldhq 3,5,3',4'-tetraacetate (13), 7-O-methyldhq 3,3',4'-triacetate (14), 5-O-methyldhq 7,3',4'triacetate (25), and 7-O-methyldhq 3-acetate (12), respectively. The methylation of 8 is accompanied by intermolecular acetyl migration from phenolic oxygen to the hydroxy group of the heterocyclic ring. 5-O-Methyldhq (28) is accessible by deacetylation of 25. 5,7-Di-O-methyldhq (29), four known methyl ethers, 13 new and three known methyl ether acetates of dhq, and six new isomers with 2,3-cis stereochemistry were spectroscopically identified.
• 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。
• AGNIHOTRI, V. K.;SRIVASTAVA, S. D.;SRIVASTAVA, S. K.;PIIRE, S.;RUSIA, K., INDIAN J. PHARM. SCI., 49,(1987) N 2, 66-69
  作者：AGNIHOTRI, V. K.、SRIVASTAVA, S. D.、SRIVASTAVA, S. K.、PIIRE, S.、RUSIA, K.

  DOI：——

  日期：——