7-hydroxy-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone | 370583-62-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 7-hydroxy-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone
• 英文别名: 7-hydroxy-4-(4-methoxyphenyl)-8-methylcoumarin；7-oxy-4-(4-methoxyphenyl)-8-methylcoumarin；7-hydroxy-8-methyl-4-(4-methoxyphenyl)coumarin；7-hydroxy-4-(4-methoxyphenyl)-8-methyl-2H-chromen-2-one；7-hydroxy-4-(4-methoxyphenyl)-8-methylchromen-2-one
• CAS: 370583-62-3
• 化学式: C₁₇H₁₄O₄
• mdl: MFCD02222114
• 分子量: 282.296
• InChiKey: PRLPBOOVTNGOJN-UHFFFAOYSA-N

物化性质

• 熔点：
  262-263 °C(Solv: isopropanol (67-63-0))
• 沸点：
  487.3±45.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  7-hydroxy-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone 在 sodium hydroxide 、 potassium carbonate 作用下， 以 异丙醇 、 丙酮 为溶剂， 反应 4.0h， 生成 3-(4-fluorophenyl)-5-(4-methoxyphenyl)-9-methyl-7H-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  摘要：

  The MacLeod method was used to synthesize a series of substituted 5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-ones, modified analogs of psoralen, from 7-hydroxy-4-(4-methoxyphenyl)coumarins.

  DOI：

  10.1023/a:1022626402415
• 作为产物：
  描述：

  2,6-二羟基甲苯 、 3-(4-甲氧苯基)-3-氧代丙酸乙酯 在 硫酸 作用下， 以 乙醇 为溶剂， 以76%的产率得到7-hydroxy-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone
  参考文献：
  名称：

  摘要：

  The MacLeod method was used to synthesize a series of substituted 5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-ones, modified analogs of psoralen, from 7-hydroxy-4-(4-methoxyphenyl)coumarins.

  DOI：

  10.1023/a:1022626402415

文献信息

• Modified Coumarins. 19. Synthesis of Neoflavone D-Glycopyranosides
  作者：Ya. L. Garazd、M. M. Garazd、V. P. Khilya

  DOI：10.1007/s10600-006-0007-8

  日期：2005.11

  Neoflavone β-D-glucopyranosides, β-D-galactopyranosides, β-D-xylopyranosides, and α-D-arabinopyranosides were synthesized by Michael condensation of potassium salts of 7-hydroxy-4-arylcoumarins with acetobromosugars followed by deacetylation of the resulting peracetates.

  新黄酮β-D-吡喃葡萄糖苷、β-D-吡喃半乳糖苷、β-D-吡喃木糖苷和α-D-吡喃阿拉伯糖苷是通过 7-羟基-4-芳基香豆素的钾盐与乙酰溴化糖的迈克尔缩合反应合成的，然后对生成的过乙酸酯进行脱乙酰化反应。
• Synthesis, characterization and electrochemical properties of novel β 7-oxy-4-(4-methoxyphenyl)-8-methylcoumarin substituted metal-free, Zn(II) and Co(II) phthalocyanines
  作者：Zafer Odabaş、Hatice Kara、Ali Rıza Özkaya、Mustafa Bulut

  DOI：10.1016/j.poly.2012.03.036

  日期：2012.5

  Novel metal-free (4), Co(II) (5) and Zn(II) (6) phthalocyanines bearing four 7-oxy-4-(4-methoxyphenyl)-8-methylcoumarin substituents at peripheral (β) positions have been prepared by cyclotetramerization of 4-(4-(4-methoxyphenyl)-8-methylcoumarin-7-oxy)phthalonitrile. The compounds have been characterized by elemental analysis and IR, UV–Vis and MALDI-TOF mass spectroscopies. H-aggregation behaviour

  新型的无金属（4），Co（II）（5）和Zn（II）（6）酞菁在外围（β）位置带有四个7-氧基-4-（4-甲氧基苯基）-8-甲基香豆素取代基通过4-（4-（4-甲氧基苯基）-8-甲基香豆素-7-氧基）邻苯二甲腈的环四聚制备。该化合物已通过元素分析和IR，UV-Vis和MALDI-TOF质谱进行了表征。已在不同溶剂介质中研究了化合物的H聚集行为。此外，通过伏安法和原位光谱电化学法在二甲基亚砜和二氯甲烷中检测了配合物的氧化还原性质。通常，化合物4和6化合物5显示了基于配体的单电子氧化还原过程，而化合物5同时显示了基于配体和金属的过程，此外还存在一对与7-羟基-4-（4-甲氧基苯基）-8-甲基香豆素取代基还原相对应的过程。 。电化学和原位光谱电化学数据均表明，这些配合物的氧化还原过程因其高聚集趋势而变得复杂。
• Peripheral octa-substituted metal-free, cobalt(II) and zinc(II) phthalocyanines bearing coumarin and chloro groups: Synthesis, characterization, spectral and electrochemical properties
  作者：Selçuk Altun、Ali Rıza Özkaya、Mustafa Bulut

  DOI：10.1016/j.poly.2012.08.080

  日期：2012.11

  Novel octa-substituted metal-free, cobalt(II) and zinc(II) phthalocyanines have been synthesized by using chloro and/or coumarin substituted phthalonitrile derivatives. The compounds were characterized by UV-Vis, IR, H-1 NMR, and MALDI-TOF mass spectrometry and elemental analysis. The effects of substituents, metals, solvents and concentration on spectroscopic properties and aggregation behaviour of the novel Pcs were investigated. Furthermore, the redox properties of the octa-4-(4-methoxyphenyl)-7-oxo-8-methylcoumarin-substituted compounds were examined in dimethylsulfoxide and dichloromethane by voltammetry and in situ spectroelectrochemistry. Metal-free phthalocyanine and zinc phthalocyanine displayed ligand-based one-electron redox processes whereas cobalt phthalocyanine showed both ligand- and metal-based processes. A couple corresponding to the reduction of 4-(4-methoxyphenyl)-7-oxo-8-methylcoumarin substituents was also detected. The redox processes of the compounds in dimethylsulfoxide were observed to be broad or split, due to the association of electron transfer processes by aggregation-deaggregation equilibrium. (C) 2012 Elsevier Ltd. All rights reserved.
• Novel alpha-7-oxy-4-(4-methoxyphenyl)-8-methylcoumarin substituted metal-free, Co(II) and Zn(II) phthalocyanines: Photochemistry, photophysics, conductance and electrochemistry
  作者：Zafer Odabaş、Efe Baturhan Orman、Mahmut Durmuş、Fatih Dumludağ、Ali Rıza Özkaya、Mustafa Bulut

  DOI：10.1016/j.dyepig.2012.05.021

  日期：2012.12

  Novel alpha-substituted metal-free. Co(II) and Zn(II) phthalocyanines, bearing four 7-oxy-4-(4-methoxyphenyl)-8-methylcoumarin moieties were synthesized. The compounds were characterized by elemental analysis, IR, UV vis, H-1 NMR, C-13 NMR and MALDI-TOF mass spectroscopies. The Zn(II) phthalocyanine compound showed J-type aggregation in non-coordinating solvents. The photophysical and photochemical properties of these compounds were described in different solvents. Direct current conductivity measurements of the films of Co(II) and Zn(II) phthalocyanines as a function of temperature showed that these compounds are semiconductors with the activation energies within the range of 0.40-0.84 eV. The variation of alternating current conductivity of the films with frequency was found to be represented by the function sigma(AC) = A omega(s). The results indicated that charge transport mechanism of the films can be explained by hopping. The redox properties of the compounds were also examined in dimethylsulfoxide and dichloromethane by voltammetry and in situ spectroelectrochemistry. The compounds displayed metal and/or phthalocyanine ring-based reduction and oxidation processes. The electrochemistry of a phthalocyanine compound forming a J-aggregated species has been investigated. It was found that some redox couples of the Zn(II) compound in dichloromethane is split due to the equilibrium between its aggregated and non-aggregated species. (C) 2012 Elsevier Ltd. All rights reserved.
• ——
  作者：M. M. Garazd、Ya. L. Garazd、A. S. Ogorodniichuk、V. P. Khilya

  DOI：10.1023/a:1022626402415

  日期：——

  The MacLeod method was used to synthesize a series of substituted 5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-ones, modified analogs of psoralen, from 7-hydroxy-4-(4-methoxyphenyl)coumarins.