1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-phenyl-1,3-propanedione | 654083-31-5

• 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
• 英文名称: 1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-phenyl-1,3-propanedione
• 英文别名: 1-(2-Hydroxy-3,4,5,6-tetramethoxyphenyl)-3-phenylpropane-1,3-dione；1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-phenylpropane-1,3-dione
• CAS: 654083-31-5
• 化学式: C₁₉H₂₀O₇
• 分子量: 360.364
• InChiKey: HJXURDHHLPHOCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-phenyl-1,3-propanedione 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.03h， 以81%的产率得到5,6,7,8-四甲氧基-2-苯基色烯-4-酮
  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 吡啶 、 氢氧化钾 作用下， 以 吡啶 为溶剂， 反应 0.1h， 生成 1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-phenyl-1,3-propanedione
  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

• 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.