2'-(3,4-dimethoxybenzoyloxy)-3',4',5',6'-tetramethoxyacetophenone | 654083-33-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2'-(3,4-dimethoxybenzoyloxy)-3',4',5',6'-tetramethoxyacetophenone
• 英文别名: 3,4-dimethoxy-benzoic acid-(2-acetyl-3,4,5,6-tetramethoxy-phenyl ester)；3,4-Dimethoxy-benzoesaeure-(2-acetyl-3,4,5,6-tetramethoxy-phenylester)；Veratrumsaeure-(3.4.5.6-tetramethoxy-2-acetyl-phenylester)；(2-Acetyl-3,4,5,6-tetramethoxyphenyl) 3,4-dimethoxybenzoate
• CAS: 654083-33-7
• 化学式: C₂₁H₂₄O₉
• 分子量: 420.416
• InChiKey: HYDREDRILIMSHE-UHFFFAOYSA-N

物化性质

• 沸点：
  605.0±55.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-(3,4-dimethoxybenzoyloxy)-3',4',5',6'-tetramethoxyacetophenone 在 硫酸 、 sodium amide 、 甲苯 作用下， 生成 川陈皮素
  参考文献：
  名称：

  Horii, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1940, vol. 60, p. 614; engl. Ref. S. 246

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-羟基-3,4,5,6-四甲氧基苯基)乙-1-酮 、 3,4-二甲氧基苯甲酰氯 在 吡啶 作用下， 反应 0.03h， 以3.78 g的产率得到2'-(3,4-dimethoxybenzoyloxy)-3',4',5',6'-tetramethoxyacetophenone
  参考文献：
  名称：

  Improved, Rapid and Efficient Synthesis of Polymethoxyflavones under Microwave Irradiation and Their Inhibitory Effects on Melanogenesis

  摘要：

  The microwave-assisted methylation of 2,5-dihydroxy-1,3-dimethoxybenzene with (CH3O)(2)SO2 for 5 min gave easily 1,2,3,5-tetramethoxybenzene, which was converted into pentamethoxybenzene. The microwave-assisted Friedel-Crafts acylation of pentamethoxybenzene in the presence of In(CF3SO3)(3) gave pentamethoxyacetophenone for 15 min under solvent-free conditions in high yield. The microwave-assisted cyclization reaction of the diketones, which were synthesized from the acetophenone via three steps under microwave irradiation, gave the desired polymethoxyflavones for 1.5-3 min in high yields. The polymethoxyflavones showed inhibitory effects on melanogenesis in a human melanoma.

  DOI：

  10.3987/com-03-9891

文献信息

• Horii, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1940, vol. 60, p. 614; engl. Ref. S. 246
  作者：Horii

  DOI：——

  日期：——
• Improved, Rapid and Efficient Synthesis of Polymethoxyflavones under Microwave Irradiation and Their Inhibitory Effects on Melanogenesis
  作者：Masao Tsukayama、Yasuhiko Kawamura、Takaaki Ishizuka、Shinji Hayashi、Fumihito Torii

  DOI：10.3987/com-03-9891

  日期：——

  The microwave-assisted methylation of 2,5-dihydroxy-1,3-dimethoxybenzene with (CH3O)(2)SO2 for 5 min gave easily 1,2,3,5-tetramethoxybenzene, which was converted into pentamethoxybenzene. The microwave-assisted Friedel-Crafts acylation of pentamethoxybenzene in the presence of In(CF3SO3)(3) gave pentamethoxyacetophenone for 15 min under solvent-free conditions in high yield. The microwave-assisted cyclization reaction of the diketones, which were synthesized from the acetophenone via three steps under microwave irradiation, gave the desired polymethoxyflavones for 1.5-3 min in high yields. The polymethoxyflavones showed inhibitory effects on melanogenesis in a human melanoma.