2'-methoxy-5,7-dihydroxyflavone | 10458-35-2

• 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: 2'-methoxy-5,7-dihydroxyflavone
• 英文别名: 5,7-dihydroxy-2'-methoxyflavone；5,7-Dihydroxy-2'-methoxyflavon；2'-methoxychrysin；5,7-dihydroxy-2-(2-methoxy-phenyl)-chromen-4-one；5,7-Dihydroxy-2-(2-methoxy-phenyl)-chromen-4-on；4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(2-methoxyphenyl)-；5,7-dihydroxy-2-(2-methoxyphenyl)chromen-4-one
• CAS: 10458-35-2
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: SWYVZKGICYEZDR-UHFFFAOYSA-N

物化性质

• 熔点：
  279-282 °C
• 沸点：
  528.7±50.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  2'-methoxy-5,7-dihydroxyflavone 在 三氯化铝 、 potassium carbonate 、 丙酮 、 苯 作用下， 生成 5,7,2-三羟基黄酮
  参考文献：
  名称：

  Gupta; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 611,614

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 2-甲氧基苯酸钠 、 sodium carbonate 作用下， 生成 2'-methoxy-5,7-dihydroxyflavone
  参考文献：
  名称：

  Gupta; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 611,614

  摘要：

  DOI：

文献信息

• 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。
• Solvent-Free Synthesis of Functionalized Flavones under Microwave Irradiation
  作者：Julio A. Seijas、M. Pilar Vázquez-Tato、Raquel Carballido-Reboredo

  DOI：10.1021/jo048685z

  日期：2005.4.1

  Eco-friendly direct solvent-free synthesis of flavones is achieved by microwave irradiation of phloroglucinol and β-ketoesters. Heating with microwaves versus under classical conditions was shown to be higher yielding, cleaner, and faster. The reaction goes through a cycloaddition of an α-oxo ketene intermediate followed by an uncatalyzed thermal Fries rearrangement.

  黄酮的环保型直接无溶剂合成是通过间苯三酚和β-酮酸酯的微波辐射实现的。与在传统条件下相比，用微波加热显示出更高的产率，更清洁且更快。该反应通过α-氧代乙烯酮中间体的环加成反应，然后进行未催化的热弗里斯重排。
• Gupta; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 611,614
  作者：Gupta、Seshadri

  DOI：——

  日期：——