Synthetic method of diaryl-substituted dicarbonyl compound

A technology of a dicarbonyl compound and a synthesis method, which is applied in the field of organic chemical synthesis, can solve the problems of low product yield and the like, and achieve the effect of good application prospect and industrial production potential.

Inactive Publication Date: 2018-11-30
方美兰
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In order to overcome the defect that the product yield in the prior art is too low, and to study the new synthetic method of diaryl substituted dicarbonyl compound, the inventor has carried out in-depth research and exploration, and after paying enough creative work, thus completed this invention

Method used

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  • Synthetic method of diaryl-substituted dicarbonyl compound
  • Synthetic method of diaryl-substituted dicarbonyl compound
  • Synthetic method of diaryl-substituted dicarbonyl compound

Examples

Experimental program
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Embodiment 1

[0036]

[0037] In an appropriate amount of organic solvent at room temperature (a mixture of dimethyl sulfoxide (DMSO) and acetonitrile at a volume ratio of 3:1), add 100 mmol of the above formula (I) compound, 120 mmol of the above formula (II) compound, 20 mmol Two-component composite catalyst (composed of 10mmol 1,3-bis(diphenylphosphinopropane) nickel dichloride and 10mmol copper hexafluoroacetylacetonate), 200mmol oxidant 2-iodylbenzoic acid (IBX), 150mmol base dimethyl Aminopyridine (DMPA) and 14mmol auxiliary tetraphenylporphyrin, then heated to 70°C while stirring, and stirred and reacted at this temperature for 9 hours;

[0038] After the reaction is completed, quench the reaction with deionized water, filter, fully wash the filtrate with deionized water, then extract the organic phase with ethyl acetate for 2-3 times, combine the organic phases and dry them with anhydrous sodium sulfate, and finally distill under reduced pressure. The viscous residue obtained was...

Embodiment 2

[0041]

[0042] To an appropriate amount of organic solvent at room temperature (a mixture of dimethyl sulfoxide (DMSO) and acetonitrile at a volume ratio of 3:1), add 100 mmol of the above formula (I) compound, 180 mmol of the above formula (II) compound, 10 mmol Two-component composite catalyst (composed of 5mmol 1,3-bis(diphenylphosphinopropane) nickel dichloride and 5mmol copper hexafluoroacetylacetonate), 250mmol oxidant 2-iodylbenzoic acid (IBX), 100mmol alkali dimethyl Aminopyridine (DMPA) and 18mmol auxiliary tetraphenylporphyrin, then heated to 100°C while stirring, and stirred and reacted at this temperature for 6 hours;

[0043] After the reaction is completed, quench the reaction with deionized water, filter, fully wash the filtrate with deionized water, then extract the organic phase with ethyl acetate for 2-3 times, combine the organic phases and dry them with anhydrous sodium sulfate, and finally distill under reduced pressure. The viscous residue obtained wa...

Embodiment 3

[0046]

[0047] In an appropriate amount of organic solvent at room temperature (a mixture of dimethyl sulfoxide (DMSO) and acetonitrile at a volume ratio of 3:1), add 100 mmol of the above formula (I) compound, 150 mmol of the above formula (II) compound, 16 mmol Two-component composite catalyst (composed of 8mmol 1,3-bis(diphenylphosphinopropane) nickel dichloride and 8mmol copper hexafluoroacetylacetonate), 225mmol oxidant 2-iodylbenzoic acid (IBX), 125mmol alkali dimethyl Aminopyridine (DMPA) and 16mmol auxiliary tetraphenylporphyrin, then heated to 80°C while stirring, and stirred and reacted at this temperature for 8 hours;

[0048] After the reaction is completed, quench the reaction with deionized water, filter, fully wash the filtrate with deionized water, then extract the organic phase with ethyl acetate for 2-3 times, combine the organic phases and dry them with anhydrous sodium sulfate, and finally distill under reduced pressure. The viscous residue obtained was...

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Abstract

The invention relates to a synthetic method of a diaryl-substituted dicarbonyl compound shown as the following formula (III), the equation is shown in the description, and the synthetic method specifically comprises the steps of adding 100 mmol of a compound shown as formula (I), 130 mmol of a compound shown as formula (II), 12 mmol of a catalyst (composed of 6 mmol of 1,3-bi(diphenylphosphine propane) nickel dichloride and 6 mmol of hexafluoroacetylacetone copper), 240 mmol of 2-iodoxybenzoic acid, 110 mmol of dimethylaminopyridine and 17 mmol od tetraphenylporphyrin, then stirring and heating to 90 DEG C, and stirring for reacting for 7 hours under 90 DEG C; after the reaction is finished, quenching the reaction with deionized water, filtering, washing the filter liquor sufficiently withdeionized water, extracting an organic phase for 2 to 3 times by using ethyl acetate, combining the organic phase and drying with anhydrous sodium sulfate, finally performing reduced pressure distillation to perform chromatographic separation on the obtained thick residue by a 300 to 400-mesh silicagel column, wherein an elution solvent is a mixture of acetone and chloroform with the volume ratioof 1 to 2, thus obtaining the compound of the formula (II).

Description

[0001] This application is a divisional application with an application date of October 14, 2016, an application number of 201610895883.6, and an invention title of "a synthesis method of a diaryl-substituted dicarbonyl compound". technical field [0002] The invention relates to a synthesis method of a dicarbonyl compound, more particularly to a synthesis method of a diaryl-substituted dicarbonyl compound, and belongs to the technical field of organic chemical synthesis. Background technique [0003] The carbonyl structure is a very important type of active group in organic chemical synthesis, which can expand and change the group through a variety of reactions, so it plays an important role in organic chemical synthesis. For example, dicarbonyl compounds are a class of highly functional structural units, which are very important in drug design and functional group modification. [0004] Therefore, the development of synthetic methods for dicarbonyl compounds has attracted ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12
CPCC07D209/12
Inventor 不公告发明人
Owner 方美兰
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