8-methoxy-6,7-methylenedioxycoumarin | 81558-03-4

• 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: 8-methoxy-6,7-methylenedioxycoumarin
• 英文别名: 4-methoxy-6H-[1,3]dioxolo[4,5-g]chromen-6-one；8-methoxyayapin；sabandinin；BA-4；4-methoxy-[1,3]dioxolo[4,5-g]chromen-6-one
• CAS: 81558-03-4
• 化学式: C₁₁H₈O₅
• 分子量: 220.182
• InChiKey: GDJFGAQXNUYMPM-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C
• 沸点：
  410.8±45.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-bromo-2-hydroxy-4,5-methylenedioxybenzaldehyde 在 N,N-二乙基苯胺 、 copper dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 8-methoxy-6,7-methylenedioxycoumarin
  参考文献：
  名称：

  天然存在的ayapin衍生物的合成和结构修饰

  摘要：

  首次描述了三种高度氧化的天然香豆素，8-甲氧基-6,7-亚甲基二氧基香豆素，5-甲氧基-6,7-亚甲基二氧基香豆素和5,8-二甲氧基-6,7-亚甲基二氧基香豆素的合成。一种新的制备ayap​​in（6,7-亚甲基二氧基香豆素）的方法。合成四氧合香豆素5,8-二甲氧基-6,7-亚甲基二氧香豆素的光谱数据与文献报道的比较导致了几种天然香豆素的结构修改。两种都被鉴定为5,8-二甲氧基-6,7-亚甲基二氧基香豆素的香豆素必须具有其他结构，而另一种被称为7,8-二甲氧基-5,6-亚甲基二氧基香豆素的异构体的香豆素的结构必须修改为5 ，8-二甲氧基-6，7-亚甲基二氧基香豆素。

  DOI：

  10.1016/j.tet.2004.12.061

文献信息

• A High-Yield Method for the Methylenation of<i>o</i>-Dihydroxyaromatic Compounds: Synthesis of Methylenedioxycoumarins
  作者：P. Castillo、J. C. Rodriguez-Ubis、F. Rodriguez

  DOI：10.1055/s-1986-31796

  日期：——

  Reaction of o-dihydroxycoumarins and catechols with sodium hydride in hexamethylphosphoric triamide and dihalomethane provides the corresponding methylenedioxy compounds under mild conditions and in excellent yields.

  在六甲基膦酰胺和二氟甲烷中，o-二羟基香豆素和儿茶酚与氢化钠反应，可以在温和条件下以优异的产率生成相应的亚甲基二氧化合物。
• 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.
• CASTILLO P.; RODRIGUEZ-UBIS J. C.; ROODRIGUEZ F., SYNTHESIS,(1986) N 10, 839-840
  作者：CASTILLO P.、 RODRIGUEZ-UBIS J. C.、 ROODRIGUEZ F.

  DOI：——

  日期：——
• Synthesis and structural revision of naturally occurring ayapin derivatives
  作者：Dominick Maes、Stijn Vervisch、Silvia Debenedetti、Carlos Davio、Sven Mangelinckx、Nicola Giubellina、Norbert De Kimpe

  DOI：10.1016/j.tet.2004.12.061

  日期：2005.2

  The synthesis of three highly oxygenated naturally occurring coumarins, 8-methoxy-6,7-methylenedioxycoumarin, 5-methoxy-6,7-methylenedioxycoumarin and 5,8-dimethoxy-6,7-methylenedioxycoumarin is described for the first time, together with a new method for the preparation of ayapin (6,7-methylenedioxycoumarin). Comparison of the spectroscopic data of the synthetic tetraoxygenated coumarin 5,8-dimethoxy-6

  首次描述了三种高度氧化的天然香豆素，8-甲氧基-6,7-亚甲基二氧基香豆素，5-甲氧基-6,7-亚甲基二氧基香豆素和5,8-二甲氧基-6,7-亚甲基二氧基香豆素的合成。一种新的制备ayap​​in（6,7-亚甲基二氧基香豆素）的方法。合成四氧合香豆素5,8-二甲氧基-6,7-亚甲基二氧香豆素的光谱数据与文献报道的比较导致了几种天然香豆素的结构修改。两种都被鉴定为5,8-二甲氧基-6,7-亚甲基二氧基香豆素的香豆素必须具有其他结构，而另一种被称为7,8-二甲氧基-5,6-亚甲基二氧基香豆素的异构体的香豆素的结构必须修改为5 ，8-二甲氧基-6，7-亚甲基二氧基香豆素。