5,8-dihydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone | 2798-22-3

• 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-6,7-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone
• 英文别名: 5,8-dihydroxy-6,7,4'-trimethoxyflavone；pedunculin；8-hydroxysalvigenin；5,8-dihydroxy-6,7-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one；5,8-Dihydroxy-6,7-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-on；5,8-Dihydroxy-6,7,4'-trimethoxy-flavon；5,8-dihydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 2798-22-3
• 化学式: C₁₈H₁₆O₇
• 分子量: 344.321
• InChiKey: ZNLSNAZJVYNXLN-UHFFFAOYSA-N

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-6,7-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone 在 氢碘酸 、 乙酸酐 作用下， 生成 NSC76988
  参考文献：
  名称：

  Murti et al., Proceedings - Indian Academy of Sciences, Section A, 1947, # 26, p. 182,186

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-(2-羟基-4,6-二甲氧基苯基)-3-(4-甲氧基苯基)-2-丙烯-1-酮 在 吡啶 、 碘 、 二甲基二环氧乙烷 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 9.83h， 生成 5,8-dihydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone
  参考文献：
  名称：

  Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.01.023

文献信息

• Synthesis of 5,8-dihydroxy-6,7-dimethoxyflavones and revised structures for some natural flavones
  作者：T Horie

  DOI：10.1016/0031-9422(95)00070-n

  日期：1995.7

  7-trimethoxyflavones were synthesized from 2′,5′-dihydroxy-3′,4′,6′-trimethoxyacetophenone by adapting the selective O -alkylation and dealkylation, and the differentiation between the flavones and their isomeric 6-hydroxyflavones was clarified by 1 H NMR and UV spectra. Four natural flavones proposed as 5,8-dihydroxy-6,7-dimethoxyflavones, must have other structures and three are shown to be the isomeric

  摘要 以 2',5'-二羟基-3',4',6'-三甲氧基苯乙酮为原料，合成了 6 个 5,8-二羟基-6,7-二甲氧基黄酮和 3 个 8-羟基-5,6,7-三甲氧基黄酮。选择性O-烷基化和脱烷基化，黄酮和它们的异构体6-羟基黄酮之间的区别通过 1 H NMR 和紫外光谱得到澄清。四种天然黄酮被提议为 5,8-二羟基-6,7-二甲氧基黄酮，必须具有其他结构，其中三种被证明是异构的 5,7-二羟基-6,8-二甲氧基黄酮。从 Ageratum conyzoides 中分离出的黄酮被正确识别为 8-hydroxy-5,6,7,3',4',5'-六甲氧基黄酮，但从蜡菊中分离出的黄酮的结构被修改为异构体 7 -羟基-5,6,8-三甲氧基黄酮。
• Brahmachari; Gorai; Chatterjee, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2004, vol. 43, # 1, p. 219 - 222
  作者：Brahmachari、Gorai、Chatterjee、Mondal、Mistri

  DOI：——

  日期：——
• 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 et al., Proceedings - Indian Academy of Sciences, Section A, 1947, # 26, p. 182,186
  作者：Murti et al.

  DOI：——

  日期：——