5,6,7-trihydroxy-3',4'-dimethoxyflavone | 67197-55-1

• 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: 5,6,7-trihydroxy-3',4'-dimethoxyflavone
• 英文别名: 2-(3,4-Dimethoxyphenyl)-5,6,7-trihydroxy-4H-1-benzopyran-4-one；2-(3,4-dimethoxyphenyl)-5,6,7-trihydroxychromen-4-one
• CAS: 67197-55-1
• 化学式: C₁₇H₁₄O₇
• 分子量: 330.294
• InChiKey: FYJMAQSQFBHWFI-UHFFFAOYSA-N

物化性质

• 熔点：
  254 °C
• 沸点：
  611.0±55.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  5,6,7-trihydroxy-3',4'-dimethoxyflavone 在 氢溴酸 、 溶剂黄146 作用下， 反应 23.0h， 以82%的产率得到6-羟基四羟黄酮
  参考文献：
  名称：

  Importance of the B Ring and Its Substitution on the α-Glucosidase Inhibitory Activity of Baicalein, 5,6,7-Trihydroxyflavone

  摘要：

  为了评估黄芩素（5,6,7-三羟基黄酮，1）的 B 环对其强效α-葡萄糖苷酶抑制活性的贡献，我们制备了羟基色酮和 B 环取代的 5,6,7- 三羟基黄酮。缺乏 6-羟基取代的羟基色酮没有显示出任何抑制活性，而 5,6,7-三羟基-2-甲基色酮（5）则显示出较高的活性。在测试的 B 环取代的 5,6,7-三羟基黄酮中，4′-羟基、3′,4′-二羟基和 3′,4′,5′-三羟基取代的衍生物的活性高于 1。结果表明，1 的 B 环虽然对活性有利，但并不是必需的；5,6,7-三羟基黄酮 B 环上的羟基取代对活性有利，而甲氧基取代则不利；5,6,7-三羟基黄酮至少需要 4′-羟基取代才能提高活性，羟基的数量与活性无关。

  DOI：

  10.1271/bbb.68.1858
• 作为产物：
  描述：

  4'-甲基金圣草黄素 在 sodium hydroxide 、 双氧水 、 溶剂黄146 、 zinc(II) chloride 作用下， 反应 5.0h， 生成 5,6,7-trihydroxy-3',4'-dimethoxyflavone
  参考文献：
  名称：

  Importance of the B Ring and Its Substitution on the α-Glucosidase Inhibitory Activity of Baicalein, 5,6,7-Trihydroxyflavone

  摘要：

  为了评估黄芩素（5,6,7-三羟基黄酮，1）的 B 环对其强效α-葡萄糖苷酶抑制活性的贡献，我们制备了羟基色酮和 B 环取代的 5,6,7- 三羟基黄酮。缺乏 6-羟基取代的羟基色酮没有显示出任何抑制活性，而 5,6,7-三羟基-2-甲基色酮（5）则显示出较高的活性。在测试的 B 环取代的 5,6,7-三羟基黄酮中，4′-羟基、3′,4′-二羟基和 3′,4′,5′-三羟基取代的衍生物的活性高于 1。结果表明，1 的 B 环虽然对活性有利，但并不是必需的；5,6,7-三羟基黄酮 B 环上的羟基取代对活性有利，而甲氧基取代则不利；5,6,7-三羟基黄酮至少需要 4′-羟基取代才能提高活性，羟基的数量与活性无关。

  DOI：

  10.1271/bbb.68.1858

文献信息

• Studies of the selective O-alkylation and dealkylation of flavonoids. 13. An improved method for synthesizing 5,6,7-trihydroxyflavones from 6-hydroxy-5,7-dimethoxyflavones
  作者：Tokunaru Horie、Hideaki Tominaga、Yasuhiko Kawamura、Toshihide Yamada

  DOI：10.1021/jo00038a023

  日期：1992.6

  The demethylation of five 6-hydroxy-5,7-dimethoxyflavones 1 and their acetates with 30% w/v anhydrous aluminum chloride in acetonitrile was studied, and the following results were found. In the demethylation of 6-hydroxy-4',5,7-trimethoxyflavone (1a), 5,6-dihydroxy-4',7-dimethoxyflavone (2a) and 5,6,7-trihydroxy-4'-methoxyflavone (3a) were produced. Although the ratio of the two products varied according to the amount of aluminum chloride used, it became constant after 12-24 h because the cleavage of the 7-methoxy group in 2a was suppressed by iminoesterification of the 6-hydroxy group. In contrast, the demethylation of the 5- and 7-methoxy groups of acetate 4a proceeded smoothly by the process shown in Scheme II. The amount of 3a increased with increasing reaction time to give 3a as the main product after 36-48 h. The same phenomena were observed in the demethylation of the other 6-hydroxyflavones 1b-1e and their acetates 4b-4e. The demethylation of the acetates is widely applicable as a general method for synthesizing 5,6,7-trihydroxyflavones because the protection of hydroxy groups also suppresses the further cleavage of the methoxy group adjacent to the acetoxy group on the B ring of compounds such as 4d and 4e.
• HORIE TOKUHARU, NIXON KAGAKU KAJSI, NIRRON KAGAKU KAISNI, J. CHEM. SOS. JAR., CHEM. AND I+
  作者：HORIE TOKUHARU

  DOI：——

  日期：——
• Importance of the B Ring and Its Substitution on the α-Glucosidase Inhibitory Activity of Baicalein, 5,6,7-Trihydroxyflavone
  作者：Hong GAO、Jun KAWABATA

  DOI：10.1271/bbb.68.1858

  日期：2004.1

  Hydroxychromones and B-ring-substituted 5,6,7-trihydroxyflavones were prepared to evaluate the contribution of the B ring of baicalein (5,6,7-trihydroxyflavone, 1) to its potent α-glucosidase inhibitory activity. Hydroxychromones, which lack 6-hydroxyl substitution, did not show any inhibitory activity, while 5,6,7-trihydroxy-2-methylchromone (5) showed high activity. Among the tested B-ring-substituted 5,6,7-trihydroxyflavones, the 4′-hydroxy-, 3′,4′-dihydroxy-, and 3′,4′,5′-trihydroxy-substituted derivatives were found to give more activity than that of 1. The methoxy-substituted derivatives, however, showed less activity than 1. The results suggest that the B ring of 1 was not essential, although advantageous to the activity; hydroxyl substitution on the B ring of 5,6,7-trihydroxyflavones was favorable to the activity, whereas methoxyl substitution was unfavorable; at least 4′-hydroxyl substitution of 5,6,7-trihydroxyflavones was required for enhanced activity, in which the number of hydroxyl groups did not take part.

  为了评估黄芩素（5,6,7-三羟基黄酮，1）的 B 环对其强效α-葡萄糖苷酶抑制活性的贡献，我们制备了羟基色酮和 B 环取代的 5,6,7- 三羟基黄酮。缺乏 6-羟基取代的羟基色酮没有显示出任何抑制活性，而 5,6,7-三羟基-2-甲基色酮（5）则显示出较高的活性。在测试的 B 环取代的 5,6,7-三羟基黄酮中，4′-羟基、3′,4′-二羟基和 3′,4′,5′-三羟基取代的衍生物的活性高于 1。结果表明，1 的 B 环虽然对活性有利，但并不是必需的；5,6,7-三羟基黄酮 B 环上的羟基取代对活性有利，而甲氧基取代则不利；5,6,7-三羟基黄酮至少需要 4′-羟基取代才能提高活性，羟基的数量与活性无关。