2'-acetoxy-3',4',5'-trimethoxyacetophenone | 6953-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-acetoxy-3',4',5'-trimethoxyacetophenone
• 英文别名: 2-Acetoxy-3,4,6-trimethoxy-acetophenon；1-(2-acetoxy-3,4,6-trimethoxy-phenyl)-ethanone；1-(2-Acetoxy-3,4,6-trimethoxy-phenyl)-aethanon；2-Acetyl-3,5,6-trimethoxyphenyl acetate；(2-acetyl-3,5,6-trimethoxyphenyl) acetate
• CAS: 6953-31-7
• 化学式: C₁₃H₁₆O₆
• 分子量: 268.266
• InChiKey: NERVVHYJACMAGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-acetoxy-3',4',5'-trimethoxyacetophenone 在 sodium hydroxide 、 In(OSO₂CF₃)3 、 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 4.25h， 生成 2',3',4',5',6'-pentamethoxyacetophenone
  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：

  2,6-二甲氧基对苯二酚 在 In(OSO₂CF₃)3 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.18h， 生成 2'-acetoxy-3',4',5'-trimethoxyacetophenone
  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

• Bargellini; Zoras, Gazzetta Chimica Italiana, 1934, vol. 64, p. 192,197; s.a. E I 732; E II 533
  作者：Bargellini、Zoras

  DOI：——

  日期：——
• Bargellini; Bini, Gazzetta Chimica Italiana, 1911, vol. 41 II, p. 17
  作者：Bargellini、Bini

  DOI：——

  日期：——
• TAKEDA, YOSHIO;FATOPE, MAJEKODUNMI O., J. NATUR. PROD., 51,(1988) N 4, C. 725-729
  作者：TAKEDA, YOSHIO、FATOPE, MAJEKODUNMI O.

  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.