(2R,3R)-dihydroquercetin-7,3'-dimethyl ether | 37971-67-8

• 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: (2R,3R)-dihydroquercetin-7,3'-dimethyl ether
• 英文别名: (2R,3R)-2,3-Dihydro-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one；(2R,3R)-3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
• CAS: 37971-67-8
• 化学式: C₁₇H₁₆O₇
• 分子量: 332.31
• InChiKey: DQZRHRLTSJNVBC-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R)-dihydroquercetin-7,3'-dimethyl ether 、 乙酸酐 以 吡啶 为溶剂， 反应 24.0h， 生成 Acetic acid (2R,3R)-3-acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-7-methoxy-4-oxo-chroman-5-yl ester
  参考文献：
  名称：

  来自 Grindelia discoidea 的二萜类化合物和黄酮类化合物

  摘要：

  摘要 从 Grindelia discoidea 地上部分分离到了一种新的劳丹型二萜酸，即盘状酸。根据其甲酯衍生物的光谱数据并将这些数据与其异构体3β-羟基labd-的甲酯衍生物的光谱数据进行比较，推导出其结构为4β-羟基甲基labd-7-en-15-油酸。 7-en-15-油酸，也从同一提取物中分离出来。此外，已分离出一种二氢黄酮醇和两种黄酮醇。

  DOI：

  10.1016/0031-9422(86)88032-3
• 作为产物：
  描述：

  重氮甲烷 、 花旗松素 以 乙醚 、 苯 为溶剂， 反应 1.5h， 以28%的产率得到李属素
  参考文献：
  名称：

  Structure–Activity Relationship for (+)-Taxifolin Isolated from Silymarin as an Inhibitor of Amyloid β Aggregation

  摘要：

  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.

  DOI：

  10.1271/bbb.120925

文献信息

• Trixikingolides and germacrene derivatives from Trixis species
  作者：Ferdinand Bohlmann、Antoinette Suwita、Jasmin Jakupovic、Robert M. King、Harold Robinson

  DOI：10.1016/s0031-9422(00)98549-2

  日期：1981.1

  Abstract The investigation of two further Trixis species afforded five new sesquiterpenes related to trixikingolide, six new germacrene derivatives and a sesquiterpene derived from rotundene. Some further known compounds were isolated too, which in part may be of chemotaxonomic significance. The structures were elucidated by spectroscopic methods and a few chemical transformations. The relative position

  摘要 对另外两个 Trixis 物种的研究提供了 5 个与 trixikingolide 相关的新倍半萜、6 个新的锗烯衍生物和一个衍生自 rotundene 的倍半萜。一些其他已知化合物也被分离出来，这在一定程度上可能具有化学分类学意义。通过光谱方法和一些化学转化阐明了结构。然而，由于部分皂化不成功，无法确定八种新倍半萜类化合物中酯基的相对位置。
• 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.
• 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.
• Diterpenoids and flavonoids from Grindelia discoidea
  作者：Barbara N. Timmermann、Joseph J. Hoffmann、Shivanand D. Jolad、Robert B. Bates、Teruna J. Siahaan

  DOI：10.1016/0031-9422(86)88032-3

  日期：1986.1

  labdane-type diterpenoid acid, discoidic acid, has been isolated from the aerial parts of Grindelia discoidea. Its structure has been deduced as 4β-hydroxymethyllabd-7-en- 15-oic acid on the basis of the spectral data of its methyl ester derivative and comparison of these data with those of the methyl ester derivative of its isomer, 3β-hydroxylabd-7-en- 15-oic acid, also isolated from the same extract

  摘要 从 Grindelia discoidea 地上部分分离到了一种新的劳丹型二萜酸，即盘状酸。根据其甲酯衍生物的光谱数据并将这些数据与其异构体3β-羟基labd-的甲酯衍生物的光谱数据进行比较，推导出其结构为4β-羟基甲基labd-7-en-15-油酸。 7-en-15-油酸，也从同一提取物中分离出来。此外，已分离出一种二氢黄酮醇和两种黄酮醇。