ethyl (7-methoxy-2-oxo-2H-chromen-4-yl)acetate | 32632-43-2

• 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: ethyl (7-methoxy-2-oxo-2H-chromen-4-yl)acetate
• 英文别名: (7-methoxy-2-oxo-2H-chromen-4-yl)-acetic acid ethyl ester；(7-Methoxy-2-oxo-2H-chromen-4-yl)-essigsaeure-aethylester；(7-Methoxy-4-cumaryl)-essigsaeureethylester；Ethyl 2-(7-methoxy-2-oxochromen-4-yl)acetate
• CAS: 32632-43-2
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: OVMRTNYWDDQFEU-UHFFFAOYSA-N

物化性质

• 熔点：
  100-102 °C(Solv: ethanol (64-17-5))
• 沸点：
  418.8±45.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (7-methoxy-2-oxo-2H-chromen-4-yl)acetate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-[(3-benzoxy-1,6-dimethyl-4-oxo-1,4-dihydropyridin-2-yl)methyl]-2-(7-methoxy-2-oxo-2H-chromen-4-yl)acetamide
  参考文献：
  名称：

  Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors

  摘要：

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.

  DOI：

  10.1021/jm049751s
• 作为产物：
  描述：

  3-甲氧基苯酚 在 硫酸 作用下， 生成 ethyl (7-methoxy-2-oxo-2H-chromen-4-yl)acetate
  参考文献：
  名称：

  Synthetic and Structural Studies on Novel 4,3′-Bicoumarins

  摘要：

  A series of directly linked 4-3 bicoumarins have been synthesized by both Knoevenagel and Perkin reactions. This single-step transformation was accomplished by the reaction of coumarin-4-acetates with substituted salicylaldehydes in presence of piperidine using ethanol as solvent and by the reaction of coumarin-4-acetic acids with substituted salicylaldehydes in the presence of sodium hydride in acetic anhydride. Greater yields have been obtained in the sodium hydride and acetic anhydride condition. An intermediate chalcone with an ortho-hydroxyl group, which is a precursor for lactone formation, has been isolated and its structure has been confirmed by x-ray analysis. The nonplanar S-cis arrangement of two C4-C3' double bonds has been confirmed by nuclear Overhauser spectroscopy (NOE) and x-ray studies. The UV-fluorescence studies support the formation of a conjugated bicoumarin system.

  DOI：

  10.1080/00397911.2015.1063656

文献信息

• Coumarins. II. Derivatives of Coumarin-3- and -4-Acetic Acids
  作者：S. C. Laskowski、R. O. Clinton

  DOI：10.1021/ja01165a043

  日期：1950.9
• Basic esters and amides of 7-substituted-coumarin-4-acetic acids and salts and processes of preparation
  申请人：STERLING DRUG INC

  公开号：US02615024A1

  公开（公告）日：1952-10-21
• Synthetic and Structural Studies on Novel 4,3′-Bicoumarins
  作者：Kiran K. Pujar、Manohar V. Kulkarni、Ganesh N. Alawandi、G. N. Anilkumar、Mahantesha Basanagouda

  DOI：10.1080/00397911.2015.1063656

  日期：2015.9.2

  A series of directly linked 4-3 bicoumarins have been synthesized by both Knoevenagel and Perkin reactions. This single-step transformation was accomplished by the reaction of coumarin-4-acetates with substituted salicylaldehydes in presence of piperidine using ethanol as solvent and by the reaction of coumarin-4-acetic acids with substituted salicylaldehydes in the presence of sodium hydride in acetic anhydride. Greater yields have been obtained in the sodium hydride and acetic anhydride condition. An intermediate chalcone with an ortho-hydroxyl group, which is a precursor for lactone formation, has been isolated and its structure has been confirmed by x-ray analysis. The nonplanar S-cis arrangement of two C4-C3' double bonds has been confirmed by nuclear Overhauser spectroscopy (NOE) and x-ray studies. The UV-fluorescence studies support the formation of a conjugated bicoumarin system.
• Design, Synthesis, Physicochemical Properties, and Evaluation of Novel Iron Chelators with Fluorescent Sensors
  作者：Yongmin Ma、Wei Luo、Peter J. Quinn、Zudong Liu、Robert C. Hider

  DOI：10.1021/jm049751s

  日期：2004.12.1

  The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.