4-(6-methyl-4-oxo-4H-pyran-2-yl)benzaldehyde | 1173001-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(6-methyl-4-oxo-4H-pyran-2-yl)benzaldehyde
• 英文别名: 4-(6-methyl-4-oxopyran-2-yl)benzaldehyde
• CAS: 1173001-16-5
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: MPELFTLKGVOTRA-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C
• 沸点：
  429.3±45.0 °C(predicted)
• 密度：
  1.242±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基吡啶 、 异氰环已烷 、 4-(6-methyl-4-oxo-4H-pyran-2-yl)benzaldehyde 在 bismuth(III) chloride 作用下， 反应 0.05h， 以95%的产率得到2-(4-(3-(cyclohexylamino)imidazo[1,2-a]pyridin-2-yl)phenyl)-6-methyl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis, spectroscopic and DFT studies of novel fluorescent dyes: 3-Aminoimidazo[1,2-a]pyridines possessing 4-pyrone moieties

  摘要：

  A series of novel imidazo[1,2-a]pyridines possessing 4-pyrone ring were synthesized by three-component condensation of 4-pyrone carbaldehydes, 2-aminopyridines and isocyanides. Bismuth (III) chloride was used as a catalyst in these reactions and desired products were synthesized in good yields at a very short period of time under solvent free conditions. UV-Vis absorption and fluorescence emission spectra of these compounds were investigated. It shown that two of these compounds (10f and 10g) exhibit intense fluorescence in dichloromethane. Optimized ground-state molecular geometries and orbital distributions of these two fluorescent dyes were obtained using density functional theory (DFT). Thermogravimetric analysis and electrochemical properties of these compounds were also studied. (C) 2013 Published by Elsevier B.V.

  DOI：

  10.1016/j.saa.2013.09.056
• 作为产物：
  描述：

  2-(4-bromomethylphenyl)-6-methyl-4H-pyran-4-one hexaminium salt 在 水 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以43%的产率得到4-(6-methyl-4-oxo-4H-pyran-2-yl)benzaldehyde
  参考文献：
  名称：

  吡喃甲醛，吡喃鎓化物及相关环氧化物的合成

  摘要：

  4-吡喃六甲铵盐 通过处理合成 2-（4-溴甲基苯基）-6-甲基-4 H-吡喃-4-酮 和 2-（4-溴甲基苯基）-6-苯基-4 H-吡喃-4-酮 和 六甲基-亚乙基四胺在氯仿中的产率分别为71％和84％。水解的 和 在EtOH：H 2 O中产生相应的醛 和 分别有43％和58％的产量。溴吡喃酮的反应 和 和 甲醇中的二甲基硫醚：CH 2 Cl 2提供相应的sulf盐 和 分别有66％和65％的产量。治疗 和 与芳烃carbaldehydes如（AR = p -ClC 6 ħ 4，ö -ClC 6 ħ 4，p -NO 2 ç 6 ħ 4，ö -NO 2 ç 6 ħ 4，p -FC 6 ħ 4，2-萘基，p -MeOC 6 H 4，C 6 H 5 CH CH，p -MeC 6 H 4，C 6 H 5和4-（4-氧代-6-苯基-4 H-吡喃-2-基）苯甲醛 ）在CH 3 CN：H 2 O中存在

  DOI：

  10.1002/jhet.79

文献信息

• Synthesis of pyrone carbaldehydes, pyrone sulfonium ylides and related epoxides
  作者：Aziz Shahrisa、Mahnaz Saraei

  DOI：10.1002/jhet.79

  日期：2009.3

  Hexaminium salts of 4-pyrones were synthesized by treatment of 2-(4-bromomethylphenyl)-6-methyl-4H-pyran-4-one and 2-(4-bromomethylphenyl)-6-phenyl-4H-pyran-4-one with hexamethyl-enetetramine in chloroform in 71 and 84% yields respectively. Hydrolysis of and in EtOH:H2O produced the corresponding aldehydes and in 43 and 58% yields respectively. The reaction of bromopyrones and with dimethylsulfide

  4-吡喃六甲铵盐 通过处理合成 2-（4-溴甲基苯基）-6-甲基-4 H-吡喃-4-酮 和 2-（4-溴甲基苯基）-6-苯基-4 H-吡喃-4-酮 和 六甲基-亚乙基四胺在氯仿中的产率分别为71％和84％。水解的 和 在EtOH：H 2 O中产生相应的醛 和 分别有43％和58％的产量。溴吡喃酮的反应 和 和 甲醇中的二甲基硫醚：CH 2 Cl 2提供相应的sulf盐 和 分别有66％和65％的产量。治疗 和 与芳烃carbaldehydes如（AR = p -ClC 6 ħ 4，ö -ClC 6 ħ 4，p -NO 2 ç 6 ħ 4，ö -NO 2 ç 6 ħ 4，p -FC 6 ħ 4，2-萘基，p -MeOC 6 H 4，C 6 H 5 CH CH，p -MeC 6 H 4，C 6 H 5和4-（4-氧代-6-苯基-4 H-吡喃-2-基）苯甲醛 ）在CH 3 CN：H 2 O中存在
• Synthesis, spectroscopic and DFT studies of novel fluorescent dyes: 3-Aminoimidazo[1,2-a]pyridines possessing 4-pyrone moieties
  作者：Aziz Shahrisa、Kazem Dindar Safa、Somayeh Esmati

  DOI：10.1016/j.saa.2013.09.056

  日期：2014.1

  A series of novel imidazo[1,2-a]pyridines possessing 4-pyrone ring were synthesized by three-component condensation of 4-pyrone carbaldehydes, 2-aminopyridines and isocyanides. Bismuth (III) chloride was used as a catalyst in these reactions and desired products were synthesized in good yields at a very short period of time under solvent free conditions. UV-Vis absorption and fluorescence emission spectra of these compounds were investigated. It shown that two of these compounds (10f and 10g) exhibit intense fluorescence in dichloromethane. Optimized ground-state molecular geometries and orbital distributions of these two fluorescent dyes were obtained using density functional theory (DFT). Thermogravimetric analysis and electrochemical properties of these compounds were also studied. (C) 2013 Published by Elsevier B.V.