3,6-dihydroxy-2,4-dimethoxybenzaldehyde | 105827-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,6-dihydroxy-2,4-dimethoxybenzaldehyde
• 英文别名: 3,6-dihydroxy-2,4-dimethoxy-benzaldehyde；3,6-Dihydroxy-2,4-dimethoxy-benzaldehyd
• CAS: 105827-22-3
• 化学式: C₉H₁₀O₅
• 分子量: 198.175
• InChiKey: YGEADOSKHWOPKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,6-dihydroxy-2,4-dimethoxybenzaldehyde 在 氢氧化钾 、 三氯化硼 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 7.0h， 生成 5,6'-dihydroxy-2',3',4',6,7-pentamethoxyflavone
  参考文献：
  名称：

  Flavonoids synthesis. I. Synthesis and spectroscopic properties of flavones with two hydroxy and five methoxy groups at C-2',3',4',5,6,6',7 and C-2',3,4',5,5',6,7.

  摘要：

  合成了四种2'、3'、4'、6'位羟基化的黄酮及七种2'、4'、5'位羟基化的黄酮醇，它们均在A环的5、6、7位上羟基化，与brickellin和apulein进行对比，确认了brickellin和apulein的结构分别为2'，5'-二羟基-3'，4'，5'，6'，7-五甲氧基黄酮及2'，5-二羟基-3'，4'，5，6，7-五甲氧基黄酮。根据波谱数据讨论了2'、3'、4'、6'位羟基化的黄酮及C-2'、4'、5'位羟基化的黄酮醇之间的区别。

  DOI：

  10.1248/cpb.34.1656
• 作为产物：
  描述：

  2,6-二甲氧基-1,4-苯醌 在 盐酸 、 乙醚 、 zinc(II) chloride 作用下， 生成 3,6-dihydroxy-2,4-dimethoxybenzaldehyde
  参考文献：
  名称：

  Spaeth; Jerzmanowska-Sienkiewiczowa, Chemische Berichte, 1937, vol. 70, p. 698,701

  摘要：

  DOI：

文献信息

• Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
  作者：Dominick Maes、Maria Eugenia Riveiro、Carina Shayo、Carlos Davio、Silvia Debenedetti、Norbert De Kimpe

  DOI：10.1016/j.tet.2008.02.059

  日期：2008.5

  The synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5

  描述了五种天然存在的多加氧香豆素的合成。它涉及两个5,6,7-三加氧香豆素，即6-羟基-5,7-二甲氧基香豆素（fraxinol）1和5,6,7-三甲氧基香豆素2，以及三个5,7,8-三加氧的香豆素，即8-羟基-5,7-二甲氧基（leptodactylone）3，5,7,8- trimethoxycoumarin 4和8-（3-甲基-2-丁烯氧基）-5,7-二甲氧基（artanin）5。合成途径的关键特征是合成合适的四氧化苯甲醛，然后通过维蒂希反应将其转化为相应的香豆素。
• Chapman; Perkin; Robinson, Journal of the Chemical Society, 1927, p. 3020
  作者：Chapman、Perkin、Robinson

  DOI：——

  日期：——
• Ponniah; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 544,547
  作者：Ponniah、Seshadri

  DOI：——

  日期：——
• Balaiah et al., Proceedings - Indian Academy of Sciences, Section A, 1942, # 16, p. 68,77
  作者：Balaiah et al.

  DOI：——

  日期：——
• Toward establishing structure–activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells
  作者：María E. Riveiro、Dominick Maes、Ramiro Vázquez、Monica Vermeulen、Sven Mangelinckx、Jan Jacobs、Silvia Debenedetti、Carina Shayo、Norbert De Kimpe、Carlos Davio

  DOI：10.1016/j.bmc.2009.08.002

  日期：2009.9

  The presumption that some coumarins might be lead compounds in the search for new differentiation agents against leukemia is based on the fact that natural coumarins, 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin (C-2) and 5-methoxy-6,7-methylenedioxycoumarin (C-1) inhibit proliferation and induce differentiation in U-937 cells [Riveiro, M. E.; Shayo, C.; Monczor, F.; Fernandez, N.; Baldi, A.; De Kimpe, N.; Rossi, J.; Debenedetti, S.; Davio, C. Cancer Lett. 2004, 210, 179-188]. These promising findings prompted us to investigate the anti-leukemia activity of a broader range of related polyoxygenated coumarins. Twenty related natural or synthetically prepared coumarins, including a range of 5-substituted ayapin derivatives which have become easy accessible via newly developed synthesis methods, were evaluated, where treatments with 5-(2,3-dihydroxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-3) and 5-(2-hydroxy-3-methoxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-2) were able to inhibit the cell growth and induce the differentiation of U-937 cells after 48 h treatment. These results provide insight into the correlation between some structural properties of polyoxygenated coumarins and their in vitro leukemic differentiation activity. (C) 2009 Elsevier Ltd. All rights reserved.