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Preparing method of 9,10-phenanthraquinone compound

The technology of a compound, phenanthrenequinone, applied in the field of organic compound synthesis, can solve the problems of many by-products, high cost, and difficulty in obtaining raw materials, and achieve the effects of mild reaction conditions, energy saving, and strong substrate universality

Active Publication Date: 2016-03-02
HUAWEI TEHCHNOLOGIES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problems of high oxidant price, environmental pollution, cumbersome operation, many by-products, high cost, low yield and difficult acquisition of raw materials in the current method for synthesizing phenanthrenequinones, the present invention proposes a 9, The preparation method of 10-phenanthrene quinone compounds, the method of the present invention overcomes the shortcomings of the prior art, the synthesis method of the present invention has the advantages of cheap and easy-to-obtain catalyst and low toxicity, easy-to-obtain oxygen source and environment-friendly, mild reaction conditions, functional group Good universality and easy operation

Method used

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  • Preparing method of 9,10-phenanthraquinone compound
  • Preparing method of 9,10-phenanthraquinone compound
  • Preparing method of 9,10-phenanthraquinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Add 0.2mmol of 1-p-chlorophenyl-3-(2'-phenyl)phenyl-2-allyl ketone, 0.4mmol of Selectfluor, and 0.02mmol of Cu powder into a 10mL reaction tube, then add 2mL of acetonitrile / water (V:V= 50:1) as solvent. Then, magnetically stir at 25° C. for 12 h. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate=6:1 as an eluent). The material was an orange-red solid in 76% yield.

[0026] Characterization data: 1 HNMR (CDCl 3 , 400MHz): 8.17-8.15(m, 2H), 7.99(d, J=8Hz, 2H), 7.73-7.68(m, 2H), 7.48-7.44(m, 2H); 13 CNMR (CDCl 3 , 100MHz): δ180.3, 136.0, 135.8, 131.0, 130.5, 129.6, 124.0; MS (EI, 70eV): m / z (%) = 208 [M + ].

Embodiment 2

[0028]

[0029] Add 0.2mmol of 1-p-chlorophenyl-3-(2'-m-methylphenyl)phenyl-2-allyl ketone, 0.4mmol of Selectfluor, and 0.02mmol of Cu powder into a 10mL reaction tube, then add 2mL of acetonitrile / water (V : V=50:1) as solvent. Then, magnetically stir at 25° C. for 12 h. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate=6:1 as an eluent). The material was an orange-red solid in 80% yield.

[0030] Characterization data: 1 HNMR (CDCl 3 , 400MHz): 8.05-8.03(m, 1H), 7.93(d, J=8Hz, 1H), 7.86(d, J=8Hz, 1H), 7.65(s, 1H), 7.61-7.57(m, 1H) , 7.37-7.33(m, 1H), 7.14(d, J=7.6Hz, 1H), 2.40(s, 3H); 13 CNMR (CDCl 3 , 100MHz): δ179.4, 179.2, 147.6, 142.8, 137.4, 134.4, 131.9, 131.2, 130.9, 129.6, 129.4, 129.1, 124.6, 124.1, 22.4; MS (EI, 70eV): m / z (%) ...

Embodiment 3

[0032]

[0033] Add 0.2mmol of 1-p-chlorophenyl-3-(2'-m-methylphenyl)phenyl-2-allyl ketone, 0.2mmol of Selectfluor, and 0.008mmol of Cu powder into a 10mL reaction tube, then add 2mL of acetonitrile / water (V : V=50:1) as solvent. Then, magnetically stir at 25° C. for 12 h. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate=6:1 as an eluent). The material was an orange-red solid in 56% yield.

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Abstract

The invention belongs to the technical field of organic compound syntheses, and provides a preparing method of a 9,10-phenanthraquinone compound. The preparing method aims at solving the problems that as for methods for synthesizing 9,10-phenanthraquinone compounds at present, the price of an oxidizing agent is high, the environment is polluted, operation is complex, the number of by-products is large, cost is high, the yield is low, and raw materials are not easy to obtain. The preparing method includes the steps that substituted methylphenylacetic chalcone serves as a starting material, copper powder serves as a catalyst, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate) serves as an oxidizing agent, the mixture is reacted in a solvent for 12 hours to 24 hours at the temperature of 25 DEG C to 80 DEG C, and the 9,10-phenanthraquinone compound is obtained. The defects in the prior art are overcome through the preparing method, and the synthesizing method has the advantages that the catalyst is low in price and easy to obtain, toxicity is small, an oxygen source is easy to obtain, the environment-friendly effect is achieved, the reaction condition is mild, functional-group universality is good, and operation is easy and convenient.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of 9,10-phenanthrenequinone compounds. Background technique [0002] Phenanthrenequinones are an important class of natural products with significant physiological activities, such as anti-tumor, anti-inflammatory, antibacterial, etc. Phenanthrenequinones show different biological activities due to different oxidation positions. 9,10-phenanthrenequinones It is often used as an antibacterial agent; in the dye industry, phenanthrenequinone is an important raw material for the synthesis of certain dyes, for example, phenanthrenequinone is nitrated to synthesize 2-aminophenanthrenequinone, which can directly dye wool fabrics gray; in addition, phenanthrenequinone compounds are An important class of chemical raw materials, which can be used to synthesize chemical intermediates such as trinitrobiphenyl dicarboxylic acid and 9-hydroxyflu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C46/02C07C50/16C07C50/24C07D333/50
Inventor 刘运奎张家慧吴德贵
Owner HUAWEI TEHCHNOLOGIES CO LTD
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