1,3-丙二酮,1-(2-羟基-3,4,5,6-四甲氧苯基)-3-(4-甲氧苯基)- | 111497-80-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1,3-丙二酮,1-(2-羟基-3,4,5,6-四甲氧苯基)-3-(4-甲氧苯基)-
• 英文名称: 1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(4-methoxyphenyl)-1,3-propanedione
• 英文别名: 1-(2-hydroxy-3,4,5,6-tetramethoxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione；1-(2-Hydroxy-3,4,5,6-tetramethoxy-phenyl)-3-(4-methoxy-phenyl)-propan-1,3-dion；1-(2-Hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(4-methoxyphenyl)propane-1,3-dione
• CAS: 111497-80-4
• 化学式: C₂₀H₂₂O₈
• 分子量: 390.39
• InChiKey: LBWVXXVARKKCDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3-丙二酮,1-(2-羟基-3,4,5,6-四甲氧苯基)-3-(4-甲氧苯基)- 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.05h， 以1.75 g的产率得到桔皮素
  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
• 作为产物：
  描述：

  1-(2-羟基-3,4,5,6-四甲氧基苯基)乙-1-酮 在 sodium amide 、 xylene 作用下， 生成 1,3-丙二酮,1-(2-羟基-3,4,5,6-四甲氧苯基)-3-(4-甲氧苯基)-
  参考文献：
  名称：

  Matsuura, Yakugaku Zasshi, 1957, vol. 77, p. 328

  摘要：

  DOI：

文献信息

• Matsuura, Yakugaku Zasshi, 1957, vol. 77, p. 328
  作者：Matsuura

  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.