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Novel pyrenyl chalcone derivative and synthesis method thereof

A technology of pyrenylchalcone and synthesis method, which is applied in the field of novel pyrenylchalcone derivatives and their synthesis, and can solve problems such as inability to react to obtain chalcone

Inactive Publication Date: 2017-05-24
赵明根
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to solve the problem in the prior art that 3-pyridinecarbaldehyde and 4-pyridinecarbaldehyde cannot react with 1-acetylpyrene under alkaline or acidic conditions to obtain chalcones containing pyrenyl and pyridyl, the present invention provides a Novel pyrenylchalcone derivatives and synthetic method thereof

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  • Novel pyrenyl chalcone derivative and synthesis method thereof
  • Novel pyrenyl chalcone derivative and synthesis method thereof
  • Novel pyrenyl chalcone derivative and synthesis method thereof

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Embodiment 1

[0060] Embodiment 1, the synthetic method of described novel pyrenylchalcone derivatives, comprises the following steps:

[0061] (1) Synthesis of 1-(pyrene-1-yl)-3-(pyridin-3-yl)propenone:

[0062] In a 250 mL round bottom flask equipped with a magnetic stirrer, add 0.24 g of 1-acetylpyrene and 35 mL of absolute ethanol successively, heat and stir to dissolve them; then add 0.25 mL of 3-pyridinecarbaldehyde and catalyst sodium acetate, the amount of catalyst added 5% of the molar mass of the remaining reactants, stirred and reacted at 40°C for 4h, a yellow solid was precipitated, during which TLC tracked the reaction (developing agent was V 乙酸乙酯 : V 石油醚 =1:7), until the complete reaction of 1-acetylpyrene, stop stirring, cool, filter with suction, wash the filter cake with water and ethanol successively, filter with suction, and dry in vacuum to obtain 0.29g of the product, which is separated by column chromatography Pure product 0.27g (the eluent used for column chromato...

Embodiment 2

[0065] Embodiment 2, the synthetic method of described novel pyrenylchalcone derivatives, comprises the following steps:

[0066] (1) Synthesis of 1-(pyrene-1-yl)-3-(pyridin-3-yl)propenone:

[0067] In a 250 mL round bottom flask equipped with a magnetic stirrer, add 0.24 g of 1-acetylpyrene and 35 mL of absolute ethanol successively, heat and stir to dissolve them; then add 0.25 mL of 3-pyridinecarbaldehyde and catalyst sodium acetate, the amount of catalyst added 7% of the molar mass of the remaining reactants, stirred and reacted at 50°C for 5h, a yellow solid was precipitated, during which TLC tracked the reaction (developing agent was V 乙酸乙酯 : V 石油醚 =1:7), until the complete reaction of 1-acetylpyrene, stop stirring, cool, filter with suction, wash the filter cake with water and ethanol successively, filter with suction, and dry in vacuum to obtain 0.28g of the product, which is separated by column chromatography Pure product 0.26g (the eluent used for column chromato...

Embodiment 3

[0070] Embodiment 3, the synthetic method of described novel pyrenylchalcone derivatives, comprises the following steps:

[0071] (1) Synthesis of 1-(pyrene-1-yl)-3-(pyridin-3-yl)propenone:

[0072] In a 250 mL round bottom flask equipped with a magnetic stirrer, add 0.24 g of 1-acetylpyrene and 35 mL of absolute ethanol successively, heat and stir to dissolve them; then add 0.25 mL of 3-pyridinecarbaldehyde and catalyst sodium acetate, the amount of catalyst added 10% of the molar mass of the remaining reactants, stirred and reacted at 60°C for 6h, a yellow solid was precipitated, during which TLC tracked the reaction (developing agent was V 乙酸乙酯 : V 石油醚 =1:7), until the complete reaction of 1-acetylpyrene, stop stirring, cool, filter with suction, wash the filter cake with water and ethanol successively, filter with suction, and dry in vacuum to obtain 0.27g of product, which is separated by column chromatography Pure product 0.25g (the eluent used for column chromatogra...

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Abstract

The invention provides a novel pyrenyl chalcone derivative and a synthesis method thereof, and belongs to the technical field of organic synthesis. The problem that 3-pyridylaldehyde and 4-pyridylaldehyde cannot react with 1-acetylpyrene under an alkaline or acid condition to obtain chalcone containing pyrenyl and pyridyl is solved. 1-(pyrene-1-yl)-3-(pyridine-3-yl) acrylketone and 1-(pyrene-1-yl)-3-(pyridine-4-yl) acrylketone are obtained through reaction of 1-acetylpyrene, absolute ethyl alcohol and 3-pyridylaldehyde (or 4-pyridylaldehyde) under the action of a catalyst at a certain temperature separately. The catalyst is high in selectivity, the method is simple and convenient, and the yield is relatively high.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a novel pyrenylchalcone derivative and a synthesis method thereof. Background technique [0002] It has been reported that chalcones are a class of cross-conjugated nonlinear optical chromophores that exhibit good SHG efficiency and transparency and are easily crystallized. Pyrene has a large π-conjugated system, and its derivatives exhibit good third-order nonlinear optical effects. Anthoni Praveen Menezes et al. reported that the charge transfer of the nonlinear optical behavior of substituted pyridyl chalcone derivatives has a directional effect, showing good molecular hyperpolarizability. C. S. Chidan Kumar et al. reported a centrosymmetric organic crystal 1-(3,4-dimethoxyphenyl)-3-(2-fluorophenyl)propenone, which was determined by open-pore Z-scan technique Its third-order nonlinear optical absorption and optical limiting experiments found that the tw...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/50C09K11/06
Inventor 石玉芳王桂林孙金鱼刘成琪赵明根
Owner 赵明根
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