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Compounding method for beta-aryl propiophenone compound

A synthesis method and compound technology are applied in the synthesis of compounds, in the field of synthesis of β-arylpropiophenone compounds, which can solve the problems of expensive precious metals, poor functional group tolerance, cumbersome experimental operations and the like, and achieve high yield and purity. Easy operation and good tolerance

Active Publication Date: 2017-11-24
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, most of the existing technologies have many defects such as cumbersome experimental operations, expensive precious metals, many side reactions, severe reaction conditions, and poor tolerance of functional groups.

Method used

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  • Compounding method for beta-aryl propiophenone compound
  • Compounding method for beta-aryl propiophenone compound
  • Compounding method for beta-aryl propiophenone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of β-phenylpropiophenone:

[0034]

[0035] At room temperature, chalcone (0.4mmol, 1equiv), selenium powder (1.2mmol, 3equiv) and KOAc (0.8mmol, 2equiv) were added to the reaction tube, then pumped-nitrogen replaced three times, and 2mL DMF was added, Stir at a reaction temperature of 150°C, monitor the end of the reaction by thin layer chromatography (about 24h), cool the reaction mixture, then add ethyl acetate for dilution, concentrate under reduced pressure, and obtain the product through column chromatography (eluent: petroleum Ether and diethyl ether are mixed according to the volume ratio of 10:1), the product is a white solid, the weight is 81.4 mg, and the yield is 97%.

[0036] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0037] 1 H NMR (500MHz, CDCl 3 ): δ7.93(d, J=7.5Hz, 2H), 7.52(t, J=7.5Hz, 1H), 7.42(t, J=7.5Hz, 2H), 7.29-7.17(m, 5H), 3.27 (t, J=7.5Hz, 2H), 3.05(t, J=7.5Hz, 2H).

[0038] ...

Embodiment 2

[0041] Synthesis of 1-phenyl-3-(p-tolyl)-propanone:

[0042]

[0043] At room temperature, (E)-1-phenyl-3-(p-tolyl)-2-propenone (0.4mmol, 1equiv), selenium powder (1.2mmol, 3equiv) and KOAc (0.8mmol, 2equiv) were added into the reaction tube, then evacuate and replace with nitrogen three times, add 2mL DMF, stir at a reaction temperature of 150°C, monitor the reaction by thin layer chromatography (about 24h), cool the reaction mixture, and then add ethyl acetate to dilute , Distilled under reduced pressure, separated by column chromatography to obtain the product (eluent: petroleum ether and diethyl ether are mixed according to the volume ratio of 10:1), the product is a light yellow solid, the weight is 82.4mg, and the yield is 92%.

[0044] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0045] 1 H NMR (500MHz, CDCl 3): δ7.95(d, J=7.0Hz, 2H), 7.53(t, J=7.5Hz, 1H), 7.43(t, J=7.5Hz, 2H), 7.15-7.09(m, 4H), 3.27 (t, J=7.5Hz, ...

Embodiment 3

[0049] Synthesis of 3-phenyl-1-(p-tolyl)-acetone:

[0050]

[0051] At room temperature, (E)-3-phenyl-1-(p-tolyl)-2-propenone (0.4mmol, 1equiv), selenium powder (1.2mmol, 3equiv) and KOAc (0.8mmol, 2equiv) were added into the reaction tube, then evacuate and replace with nitrogen three times, add 2mL DMF, stir at a reaction temperature of 150°C, monitor the reaction by thin layer chromatography (about 24h), cool the reaction mixture, and then add ethyl acetate to dilute , Distilled under reduced pressure, separated by column chromatography to obtain the product (eluent: petroleum ether and diethyl ether are mixed according to the volume ratio of 10:1), the product is a light yellow solid, the weight is 86.2 mg, and the yield is 96%.

[0052] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0053] 1 H NMR (500MHz, CDCl 3 ): δ7.84(d, J=8.0Hz, 2H), 7.28(t, J=7.5Hz, 2H), 7.23(t, J=7.0Hz, 4H), 7.18(t, J=7.0Hz, 1H ), 3.25(t, J=7.5...

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Abstract

The invention discloses a compounding method for a beta-aryl propiophenone compound. The compounding method is characterized by taking chalcone compounds as reaction substrates, and selectively chemically reducing the carbon-carbon double bonds in the reaction substrates at 100-160 DEG C under the accelerating effect of inorganic alkaline and elemental selenium under the nitrogen condition in an organic solvent, thereby acquiring the beta-aryl propiophenone compound. The invention has the beneficial effects of mild reaction condition, simple and convenient operation, high functional tolerance, high reaction efficiency, high yield and purity, simple post-processing, reasonable price and suitability for large-scale industrial production.

Description

technical field [0001] The invention relates to a compound synthesis method, in particular to a synthesis method of β-aryl propiophenone compounds, and belongs to the technical field of organic compound synthesis. Background technique [0002] β-aryl ketone organic compounds widely exist in drug molecules, inhibitors with physiological activity and functional molecules of materials. For example: sattabacin isolated from Bacillus (the compound is considered to be biologically active against herpes simplex virus type 1 (HSV1)) can inhibit the growth of VZV, the main component of the traditional Chinese medicine turmeric (ar-turmerone), a common dye structure Antioxidant, analgesic activity with analgesic activity, and cyclooxygenase inhibitor (inhibitor of cyclo-oxygenase), etc. [0003] The following are the chemical structural formulas of several common β-aryl ketone drug molecules: [0004] [0005] The traditional method of synthesizing β-aryl ketones is mainly obtain...

Claims

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Application Information

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IPC IPC(8): C07B35/02C07C45/62C07C49/782C07C49/813C07C49/84C07C221/00C07C225/22C07C319/20C07C323/22C07D207/333C07D307/46
CPCC07B35/02C07C45/62C07C221/00C07C319/20C07D207/333C07D307/46C07C49/782C07C225/22C07C323/22C07C49/813C07C49/84
Inventor 吴华悦李鸿辰刘妙昌黄小波高文霞
Owner WENZHOU UNIVERSITY
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