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A kind of synthetic method of copper-catalyzed phosphoric acid mixed ester compound

A synthesis method and compound technology are applied in the synthesis field of phosphoric acid mixed ester compounds, which can solve the problems of using toxic reagents, harsh reaction conditions, and high economic cost, and achieve the effects of convenient operation, high synthesis efficiency and broad application prospects.

Active Publication Date: 2021-07-23
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods have the following disadvantages, such as relatively high economic cost, harsh reaction conditions, use of toxic reagents and even corrosion of equipment, etc.

Method used

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  • A kind of synthetic method of copper-catalyzed phosphoric acid mixed ester compound
  • A kind of synthetic method of copper-catalyzed phosphoric acid mixed ester compound
  • A kind of synthetic method of copper-catalyzed phosphoric acid mixed ester compound

Examples

Experimental program
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Effect test

Embodiment 1

[0037]

[0038] Synthesis of diphenyl methyl phosphate: Weigh 108 μL (0.5 mmol) of diphenyl phosphoric azide, 2 mL of methanol (49.4 mmol), cuprous chloride, sodium carbonate; diphenyl phosphoric azide and cuprous chloride The substance ratio of the substance is 1:0.1; the substance ratio of diphenylphosphoryl azide and sodium carbonate is 1:0.2; the weighed reactants are sequentially added to a 25mL reaction tube with a magnet, and the The mixture was stirred on a magnetic stirrer, then heated slowly to 40°C, and the progress of the reaction was monitored by thin-layer chromatography. Under 0.1MPa, stop the reaction after 3h and cool to room temperature. The mixture was diluted with water (5 mL), and extracted with ethyl acetate (10 mL×3), and the organic phases were combined. The organic phase was washed with saturated brine (5mL), dried by adding anhydrous sodium sulfate, concentrated by filtration, separated by column chromatography, using 300-400 mesh silica gel as th...

Embodiment 2

[0042]

[0043] Synthesis of diphenyl amyl phosphate: Weigh 108 μL (0.5 mmol) of diphenyl phosphate azide, 2 mL (18.4 mmol) of n-amyl alcohol, copper nitrate, sodium carbonate; diphenyl phosphate azide and copper nitrate The ratio of the amount of diphenylphosphoryl azide to sodium carbonate is 1:0.5; the weighed reactants are added to a 25mL reaction tube with a magnet in turn, and the Stir on a magnetic stirrer, then slowly heat to 60°C, and monitor the progress of the reaction by thin-layer chromatography. Under 0.1MPa, stop the reaction after 24h and cool to room temperature. The mixture was diluted with 0.1 mol / L hydrochloric acid (5 mL), and extracted with ethyl acetate (10 mL×3), and the organic phases were combined. The organic phase was washed with saturated brine (5mL), dried by adding anhydrous sodium sulfate, concentrated by filtration, separated by column chromatography, using 300-400 mesh silica gel as the stationary phase, and mixed with different proportion...

Embodiment 3

[0047]

[0048] Synthesis of 3-methylbutyl diphenyl phosphate: Weigh 108 μL (0.5 mmol) of diphenyl phosphoric azide, 0.2 mL (1.84 mmol) of isoamyl alcohol, copper chloride, sodium carbonate, and cyclohexane; The molar ratio of diphenyl phosphoric acid nitrogen to copper chloride is 1:0.1; the molar ratio of diphenyl phosphoric azide to sodium carbonate is 1:0.5; the volume ratio of cyclohexane to isoamyl alcohol is 9 : 1; Add the weighed reactants in turn to a 25mL reaction tube with a magnet, stir on a magnetic stirrer at room temperature, then slowly heat to 60°C, and monitor the progress of the reaction with thin-layer chromatography. Under 0.1MPa, stop the reaction after 24h and cool to room temperature. The mixture was diluted with 0.1 mol / L hydrochloric acid (5 mL), and extracted with ethyl acetate (10 mL×3), and the organic phases were combined. The organic phase was washed with saturated brine (5mL), dried by adding anhydrous sodium sulfate, concentrated by filtrat...

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Abstract

A method for synthesizing copper-catalyzed phosphoric acid mixed ester compounds, mixing phosphoric azide compounds and fatty alcohols, then adding a copper catalyst, then adding a base, reacting at 20-100°C for 3-24 hours, and after post-treatment to obtain Phosphate mixed ester compounds. The present invention uses azide phosphoric acid ester compound and fatty alcohol to synthesize phosphoric acid mixed ester compound for the first time. The synthesis process only needs to add copper catalyst and catalytically metered alkali, which is simple to operate and overcomes the shortcoming of needing inert gas protection. A novel and efficient synthetic method.

Description

technical field [0001] The invention relates to the fields of organic synthesis and fine organic chemical industry, in particular to a copper-catalyzed synthesis method of phosphoric acid mixed ester compounds. Background technique [0002] Phosphate ester compounds are a very important phosphorus-containing organic compound, and phosphate mixed ester is a very important class, which has a very good market prospect and application value, and is a research hotspot today. [0003] Phosphate esters play an important role in structurally diverse natural products and bioactive compounds. The introduction of phosphate groups substantially changes the physical and chemical properties of the parent molecule, thereby changing the molecular polarization and intermolecular bonding characteristics. Phosphate ester compounds have been widely used in biology, medicine, pesticides, polymers and materials science, especially their good biological activity (D.Kim, et.al.Chemistry of Material...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/12C07F9/32
CPCC07F9/12C07F9/3229C07F9/3288
Inventor 焦林郁张泽殷晓美洪乾宁资慧马晓迅徐龙李卓
Owner NORTHWEST UNIV
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