5,6-dimethoxyflavone | 33554-48-2

• 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: 5,6-dimethoxyflavone
• 英文别名: 5,6-Dimethoxyflavon；5,6-dimethoxy-2-phenyl-chromen-4-one；5,6-Dimethoxy-2-phenyl-chromen-4-on；5,6-dimethoxy-2-phenylchromen-4-one
• CAS: 33554-48-2
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: GHLJEZSMMHWXTR-UHFFFAOYSA-N

物化性质

• 熔点：
  196 °C
• 沸点：
  458.9±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxyflavone 在 三氯化铝 、 乙醚 、 氢溴酸 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 、 丙酮 作用下， 生成 5,6-diacetoxy-2-phenyl-chromen-4-one
  参考文献：
  名称：

  204. 5：6-二羟基黄酮的合成及素丁的结构

  摘要：

  DOI：

  10.1039/jr9390000956
• 作为产物：
  描述：

  1-(3-benzoyloxy-6-hydroxy-2-methoxy-phenyl)-1-phenyl-propane-1,3-dione 在 硫酸 、 potassium carbonate 、 丙酮 作用下， 生成 5,6-dimethoxyflavone
  参考文献：
  名称：

  Nakazawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1939, vol. 59, p. 495,499; dtsch. Ref. S. 194

  摘要：

  DOI：

文献信息

• O-methylation of flavonoids by cell-free extracts of calamondin orange
  作者：Gunter Brunet、Ragai K. Ibrahim

  DOI：10.1016/0031-9422(80)85102-8

  日期：——

  hydroxyls of a number of flavonoids, indicating the existence in citrus tissues of ortho, meta, para and 3-O-methyltransferases. The latter, hitherto unreported enzyme, catalysed the formation of 3-O-methyl ethers of galangin and quercetin. The stepwise O-methylation of a number of compounds, especially quercetin and quercetagetin, tends to suggest a coordinated sequence of O-methylations on the surface

  摘要 柑桔（Citrus mitis）的无细胞提取物催化了许多类黄酮的几乎所有羟基的O-甲基化，表明柑橘组织中存在邻位、间位、对位和3-O-甲基转移酶。后者，迄今未报道的酶，催化高良姜素和槲皮素的 3-O-甲基醚的形成。许多化合物的逐步 O-甲基化，尤其是槲皮素和槲皮素，往往表明多酶复合物表面上存在协调的 O-甲基化序列。所使用的类黄酮底物的甲基受体能力与它们的羟基取代模式和它们的负电子密度分布有关。
• 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.
• Horii, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1939, vol. 59, p. 552,558; engl. Ref. S. 209, 212
  作者：Horii

  DOI：——

  日期：——
• Nakazawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1939, vol. 59, p. 524,527; dtsch. Ref. S. 199, 200
  作者：Nakazawa

  DOI：——

  日期：——
• 204. The synthesis of 5 : 6-dihydroxyflavone and the structure of primetin
  作者：Wilson Baker

  DOI：10.1039/jr9390000956

  日期：——