6-methoxy-7-(2-oxo-3-methylbutoxy)coumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-methoxy-7-(2-oxo-3-methylbutoxy)coumarin
• 英文别名: 6-Methoxy-7-(3-methyl-2-oxobutoxy)chromen-2-one
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: NCBMWSJLSVPISS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  东莨菪内酯 在 potassium carbonate 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 17.0h， 生成 6-methoxy-7-(2-oxo-3-methylbutoxy)coumarin
  参考文献：
  名称：

  Virgatol 和 Virgatenol 的合成，两种天然存在的来自 Pterocaulon virgatum (L.) DC 的香豆素和 7-(2,3-Epoxy-3-methylbutoxy)-6-methoxycoumarin，从 Conyza obscura DC 中分离

  摘要：

  首次描述了从 Pterocaulon virgatum (L.) 和 Conyza obscura DC 合成许多天然存在的香豆素。它涉及 7-(2-羟基-3-甲氧基-3-甲基丁氧基)-6-甲氧基香豆素 (virgatol, 1)、7-(2-羟基-3-甲基-3-丁烯氧基)-6-的合成甲氧基香豆素 (virgatenol, 2) 和 7-(2,3-epoxy-3-methylbutoxy)-6-methoxycoumarin (3)。此外，报道了东莨菪碱 (4) (7-hydroxy-6-methoxycoumarin) 的直接合成和新香豆素衍生物 6-methoxy-7-(2-oxo-3-methylbutoxy)coumarin 的合成。 7), 描述。众多香豆素的一个重要分类是基于核氧原子数量的任意但与生物遗传相关的系统。因此香豆素通常根据它们的氧化模式细分。7-(2-Hydroxy-

  DOI：

  10.1055/s-2004-829139

文献信息

• 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.
• Synthesis of Virgatol and Virgatenol, Two Naturally Occurring Coumarins from <i>Pterocaulon virgatum</i> (L.) DC, and 7-(2,3-Epoxy-3-methylbutoxy)-6-methoxycoumarin­, Isolated from <i>Conyza obscura</i> DC
  作者：Norbert De Kimpe、Jan Demyttenaere、Stijn Vervisch、Silvia Debenedetti、Jorge Coussio、Dominick Maes

  DOI：10.1055/s-2004-829139

  日期：——

  The synthesis of a number of naturally occurring cou- marins from Pterocaulon virgatum (L.) and Conyza obscura DC is described for the first time. It concerns the synthesis of 7-(2-hy- droxy-3-methoxy-3-methylbutoxy)-6-methoxycoumarin (virgatol, 1), 7-(2-hydroxy-3-methyl-3-butenyloxy)-6-methoxycoumarin (virgatenol, 2) and 7-(2,3-epoxy-3-methylbutoxy)-6-methoxycou- marin (3). In addition, a straightforward

  首次描述了从 Pterocaulon virgatum (L.) 和 Conyza obscura DC 合成许多天然存在的香豆素。它涉及 7-(2-羟基-3-甲氧基-3-甲基丁氧基)-6-甲氧基香豆素 (virgatol, 1)、7-(2-羟基-3-甲基-3-丁烯氧基)-6-的合成甲氧基香豆素 (virgatenol, 2) 和 7-(2,3-epoxy-3-methylbutoxy)-6-methoxycoumarin (3)。此外，报道了东莨菪碱 (4) (7-hydroxy-6-methoxycoumarin) 的直接合成和新香豆素衍生物 6-methoxy-7-(2-oxo-3-methylbutoxy)coumarin 的合成。 7), 描述。众多香豆素的一个重要分类是基于核氧原子数量的任意但与生物遗传相关的系统。因此香豆素通常根据它们的氧化模式细分。7-(2-Hydroxy-