5,8-dihydroxy-7-methoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone | 71847-58-0

• 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: 5,8-dihydroxy-7-methoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone
• 英文别名: 5,8-dihydroxy-7,3′,4′-trimethoxyflavone；5,8-Dihydroxy-7,3',4'-trimethoxyflavone；2-(3,4-dimethoxy-phenyl)-5,8-dihydroxy-7-methoxy-chromen-4-one；2-(3,4-Dimethoxy-phenyl)-5,8-dihydroxy-7-methoxy-chromen-4-on；2-(3,4-dimethoxyphenyl)-5,8-dihydroxy-7-methoxychromen-4-one
• CAS: 71847-58-0
• 化学式: C₁₈H₁₆O₇
• 分子量: 344.321
• InChiKey: WQCDSSUBTJIBOY-UHFFFAOYSA-N

物化性质

• 熔点：
  248-249 °C
• 沸点：
  586.3±50.0 °C(Predicted)
• 密度：
  1.387±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  5,8-dihydroxy-7-methoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone 在 吡啶溴化氢盐 作用下， 生成 羟基木犀草素
  参考文献：
  名称：

  Studies on Nepalese Crude Drugs. XIV. New Flavonoids from the Root of Scutellaria prostrata Jacq. ex Benth.

  摘要：

  从黄芩（唇形科植物）的根中分离出六种黄酮类化合物，分别命名为黄芩前列素 A、B、C、D、E 和 F。它们的结构被确定为：(2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-phenyl-2, 3-dihydro-7H-1, 4-dioxino[2, 3-h]chromene-7-one (I), (2R*, 3*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(4-hydroxyphenyl)-2、(2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-9-(3, 4-dihydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino-[2, 3-h]-chromene-7-one (II), (2R*, 3R*)-6-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-9-(3, 4-dihydroxyphenyl)-2, 3-dihydro-7H-1, 4-dioxino-[2, 3-h]chromene-7-one (III), (2R*、3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-phenyl-2, 3-dihydro-6H-1, 4-dioxino-[2, 3-g]chromene-6-one (IV), (2R*, 3R*)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-8-(4-hydroxyphenyl)-2, 3-dihydro-6H-1,它们是在氧化银存在下通过黄酮和针叶醇的氧化偶联合成的。

  DOI：

  10.1248/cpb.39.1466
• 作为产物：
  描述：

  4'-甲基金圣草黄素 在 吡啶 、 氢氧化钾 、 dipotassium peroxodisulfate 、 potassium carbonate 、 丙酮 作用下， 生成 5,8-dihydroxy-7-methoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone
  参考文献：
  名称：

  Rao et al., Proceedings - Indian Academy of Sciences, Section A, 1949, # 29, p. 72,75

  摘要：

  DOI：

文献信息

• Studies of the Selective<i>O</i>-Alkylation and Dealkylation of Flavonoids. VI. Demethylation of 8-Hydroxy-5,7-dimethoxyflavones with Anhydrous Aluminum Chloride or Bromide in Acetonitrile
  作者：Tokunaru Horie、Hiroki Kourai、Nobuhisa Fujita

  DOI：10.1246/bcsj.56.3773

  日期：1983.12

  with anhydrous aluminum chloride or bromide in acetonitrile was studied and the following results were obtained. (1) Anhydrous aluminum chloride in acetonitrile selectively split the 5-methoxyl group without cleavage of the 7-methoxyl group, and seven 5,8-dihydroxy-7-methoxy-flavones were quantitatively synthesized by the demethylation. (2) In the demethylation with anhydrous aluminum bromide, the

  研究了七种 8-羟基-5,7-二甲氧基黄酮与无水氯化铝或溴化铝在乙腈中的脱甲基反应，得到以下结果。(1)无水氯化铝在乙腈中选择性裂解5-甲氧基而不裂解7-甲氧基，通过脱甲基作用定量合成7个5,8-二羟基-7-甲氧基-黄酮。(2) 在无水溴化铝脱甲基反应中，4',5,7-三甲氧基-和3',4',5,7-四甲氧基-8-羟基黄酮上的5-和7-甲氧基被选择性裂解得到相应的5,7,8-三羟基黄酮收率良好。然而，去甲基化不能用于合成 5,7,8-trihydroxy-3',4',5'-trimethoxyflavone, 4',5,7,8-tetrahydroxy-3'-methoxy-, 和 3' ,5,7,8-四羟基-4'-甲氧基黄酮，因为 B 环上的甲氧基裂解。合成的黄酮被用于鉴定两种天然黄酮，它们被认为是4',5,8-tri...
• Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids
  作者：Han-Wei Chu、Huan-Ting Wu、Yean-Jang Lee

  DOI：10.1016/j.tet.2004.01.023

  日期：2004.3

  The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3',4',5,6,7,8-heptamethoxyflavone, quercetin and its derivatives were synthesized. (C) 2004 Elsevier Ltd. All rights reserved.
• Murti; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1949, # 30, p. 12
  作者：Murti、Seshadri

  DOI：——

  日期：——
• Morita, Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 66,67
  作者：Morita

  DOI：——

  日期：——
• USE OF FLAVONES, COUMARINS AND RELATED COMPOUNDS TO TREAT INFECTIONS
  申请人：Prendergast, Patrick Thomas

  公开号：EP1223928A2

  公开（公告）日：2002-07-24