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Synthesis method of Frutinone compound

A synthesis method and compound technology, applied in the direction of organic chemistry, etc., can solve the problems of less reaction steps, more reaction steps, and difficulty in obtaining, and achieve the effects of mild reaction conditions, cheap raw materials, and simple operation.

Inactive Publication Date: 2019-11-12
YANGTZE UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] This method also obtains the target product through a three-step reaction. The reaction steps are less, and the use of expensive reagents is reduced. However, the raw material replaces acetophenone compounds as precursors, which belong to regulatory chemicals, are not easy to obtain, and are mostly used. or self-synthesis, therefore, the actual reaction steps of the method are relatively more

Method used

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  • Synthesis method of Frutinone compound
  • Synthesis method of Frutinone compound
  • Synthesis method of Frutinone compound

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preparation example Construction

[0030] The embodiment of the present invention provides a kind of synthetic method of Frutinone compound, comprises the steps:

[0031] (1) in Cs 2 CO 3 Under the action of base, substituted ethyl benzoyl acetate and substituted 2-chlorobenzoyl chloride react to obtain intermediate 1;

[0032] (2) intermediate 1 and boron trihalide carry out hydrolysis reaction, obtain intermediate 2;

[0033] (3) Intermediate 2 is oxidized with potassium persulfate to obtain Frutinone compounds as target products.

[0034] In the present invention, in step (1), the following method is specifically adopted to prepare intermediate 1: alkali, Cs 2 CO 3 Mix evenly with the first solvent, add a mixture of ethyl substituted benzoyl acetate and the first solvent to the mixture at 0-5°C, mix evenly, then add substituted 2-chlorobenzoyl chloride solution, at 0°C After stirring at low temperature for 30-60 minutes, react the mixed solution at 80-130°C for 6-24 hours, and the reaction product is se...

Embodiment 1

[0056] Embodiment 1 of the present invention provides a kind of synthesis of 3A, comprises the following steps:

[0057] (1) Add t-BuONa (1mmol), Cs 2 CO 3 (1mmol) and DMAc (1mL), at 0°C, add ethyl benzoylacetate (1mmol) in DMAc (0.5mL) solution, after stirring for 15min, at 0°C, add 2-chlorobenzoyl chloride (1.2 mmol) in DMAc (1 mL) was added dropwise to the above mixture. After the addition, the resulting mixture was stirred at 0°C for 0.5h, then heated to 110°C, and kept for 8h. After the reaction was completed and cooled to normal temperature, the reaction solution was separated with ethyl acetate and water, the separated aqueous layer was extracted three times with ethyl acetate, the combined extracts were washed with brine, and washed with anhydrous Na 2 SO 4 Drying and concentration under reduced pressure afforded Intermediate 1A.

[0058] (2) Add Intermediate 1A (1mmol) and 20ml of dichloromethane into a 50ml single-necked bottle, stir and mix evenly, add BBr drop...

Embodiment 2

[0061] Embodiment 2 of the present invention provides a kind of synthesis of 3B, comprises the following steps:

[0062] (1) Add t-BuONa (1mmol), Cs 2 CO 3 (1mmol) and DMAc (1mL), at 0°C, add ethyl benzoylacetate (1mmol) in DMAc (0.5mL) solution, after stirring for 15min, at 0°C, add 2,3-dichlorobenzyl A solution of acid chloride (1.2 mmol) in DMAc (1 mL) was added dropwise to the above mixture. After the addition, the resulting mixture was stirred at 0°C for 0.5h, then heated to 110°C, and kept for 8h. After the reaction was completed and cooled to normal temperature, the reaction solution was separated with ethyl acetate and water, the separated aqueous layer was extracted three times with ethyl acetate, the combined extracts were washed with brine, and washed with anhydrous Na 2 SO 4 Drying and concentration under reduced pressure afforded Intermediate 1B.

[0063] (2) Add intermediate 1B (1mmol) and 20ml of dichloromethane into a 50ml single-necked bottle, stir and mi...

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Abstract

The invention discloses a synthesis method of a Frutinone compound, which comprises the following steps: (1) under the action of Cs2CO3 and a base, substituted ethyl benzoylacetate and substituted 2-chlorobenzoyl chloride react to obtain intermediate 1; (2) the intermediate 1 and boron trihalide are subjected to a hydrolysis reaction to obtain the intermediate 2; (3) the intermediate 2 is oxidizedwith potassium persulfate to obtain a target product. The substituted ethyl benzoylacetate, the substituted 2-chlorobenzoyl chloride, Cs2CO3, boron trihalide and potassium persulfate are used as themain raw materials, and the raw materials are cheap and easy to obtain, thus avoiding the expensive raw materials or precious metal catalysts involved in the existing methods; the synthesis method hasthe advantages of simple operation, mild reaction conditions, environmental friendliness, easy solvent recovery and application, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of frutinone compounds. Background technique [0002] Frutinones are naturally occurring structural class compounds of chromonocoumarins, present in plants of the genus Polygala such as P.dalmaisiana, P.gazensis and P.fruticosa. So far, three kinds of Frutinone A, Frutinone B and Frutinone C have been isolated. Moreover, these crude extracts of Polygala have been widely used in the treatment of various diseases. Herbal extracts of P. fruticosa have been widely used in the treatment of edema in South Africa; extracts of P. gazensis have been used in Zimbabwe to treat abdominal pain and abdominal pain disorders; in vitro experiments showed that these extracts have antifungal activity. Among them, Frutinone B. and Frutinone C have no outstanding antibacterial activity. However, Frutinone A is extremely active, has strong bactericidal activ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 吴清来鲁星亮蔡金龙
Owner YANGTZE UNIVERSITY
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