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Synthesis method of aurone compound

A synthesis method and compound technology, applied in biocides, organic chemistry, chemicals for biological control, etc., can solve the problems of many reaction steps and complicated operation, and achieve simple reaction steps, good stereoselectivity, and yield high rate effect

Inactive Publication Date: 2017-05-31
NANJING YUANSHU MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The disadvantage of this method is that there are many reaction steps and the operation is complicated.

Method used

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  • Synthesis method of aurone compound
  • Synthesis method of aurone compound
  • Synthesis method of aurone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Step 1: Add 16.4g of phenylacetylene into a double-necked round-bottom flask, add a magnetic rotor, quickly evacuate, replace the air with an inert gas, repeat twice, seal it for later use, and add anhydrous THF to it under the protection of an inert gas , Stir evenly at room temperature, put it in a -40°C ethanol bath and stir for later use, keep it at -40°C, slowly add 9.6g of n-butyllithium to it, react for 30 minutes, slowly add 12.2g of 2-hydroxybenzaldehyde for 3 hours , add saturated ammonium chloride solution to quench neutralization, remove THF by rotary evaporation, add ethyl acetate for extraction, collect the organic phase, wash the organic phase with saturated brine, add sodium sulfate to remove water and filter, collect the filtrate, and distill under reduced pressure After removing ethyl acetate, pass through a silica gel column with chloroform and petroleum ether at a volume ratio of 1:1 as the eluent to obtain 17.5 g of an intermediate product with a yie...

Embodiment 2

[0031] Step 1: Add 16.4g of phenylacetylene into a double-necked round-bottom flask, add a magnetic rotor, quickly evacuate, replace the air with an inert gas, repeat twice, seal it for later use, and add anhydrous THF to it under the protection of an inert gas , Stir evenly at room temperature, put it in an ethanol bath at minus 40°C and stir for later use, keep it at -40°C, slowly add 9.6g of n-butyllithium to it, react for 30 minutes, and slowly add 23.4g of 3,5-di-n-butyl 2-Hydroxybenzaldehyde was reacted for 2 hours, and saturated ammonium chloride solution was added to quench the neutralization. After THF was removed by rotary evaporation, ethyl acetate was added for extraction, and the organic phase was collected. The organic phase was washed with saturated brine, and sodium sulfate was added to remove water. Filtrate, collect the filtrate, remove ethyl acetate by distillation under reduced pressure, pass through a silica gel column, use chloroform and petroleum ether at...

Embodiment 3

[0037] Step 1: Add 21.8g of p-chlorophenylacetylene into a double-necked round-bottomed flask, add a magnetic rotor, quickly evacuate, replace the air with an inert gas, repeat twice, seal it for later use, and add inert gas to it under the protection of an inert gas. Water THF, stirred evenly at room temperature, then put into -40°C ethanol bath and stirred for later use, kept at -40°C, slowly added 9.6g of n-butyl lithium dropwise to it, reacted for 30 minutes, slowly added dropwise 23.4g of 2-hydroxybenzene Formaldehyde was reacted for 0.5 hours, adding saturated ammonium chloride solution to quench the neutralization, rotary evaporation to remove THF, adding ethyl acetate for extraction, collecting the organic phase, washing the organic phase with saturated brine, adding sodium sulfate to remove water and filtering, collecting the filtrate , after distilling off ethyl acetate under reduced pressure, pass through a silica gel column with chloroform and petroleum ether at a v...

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Abstract

The invention discloses a synthesis method of an aurone compound. The synthesis method comprises the following steps of (1) uniformly stirring phenylacetylene and a phenylacetylene derivative, slowly dripping n-butyllithium, reacting for 30min, and dripping a benzaldehyde derivative to react, so as to obtain an intermediate product, wherein the mass ratio of phenylacetylene to benzaldehyde derivative is 1.6:1, and the mass ratio of n-butyllithium to benzaldehyde derivative is 1.5:1; (2) adding the intermediate product obtained in step (1) into potassium carbonate powder which is equal to 2.2 molar times of the benzaldehyde derivative, adding anhydrous toluene or phenol to fully stir and dissolve under the protection of inert gas, adding lead nitrate crystal which is equal to 2.2 molar times of the benzaldehyde derivative or potassium carbonate powder which is equal to 1 molar time of the benzaldehyde derivative, heating to reflux for 2h, purifying by a silica gel column, and diluting, so as to obtain a final product. The synthesis method has the advantages that the reaction steps are simple, the yield rate of obtained aurone compound is high, and the stereo selectivity is good.

Description

technical field [0001] This patent relates to a synthetic method of orange ketones. Background technique [0002] Orange ketone [2-phenylmethylene-3-(2H)-benzofuranone], also known as aurone, is a derivative of benzofuran. Orange ketone is a secondary metabolite in plants, belonging to flavonoids, mostly found in Scrophulariaceae, Compositae, Gesneriaceae, Cyperaceae and marine organisms in monocotyledonous plants. Compared with other flavonoids (such as flavonoids, chalcones, etc.), the research on aurones is still in its infancy, but it is on the rise, and its research mainly focuses on antitumor activity, antioxidant activity, remission and treatment. Diabetic syndrome and antifeedant activity against insects. [0003] 5,7,4'-trihydroxy-3',5'-dimethoxyflavone is a rice field allelochemical isolated from allelopathic rice varieties. During the synthesis of the allelochemical, 4,6,4 '-Trihydroxy-3', 5'-dimethoxy aurone, which was first found to have herbicidal activity. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83A01P13/00
CPCC07D307/83
Inventor 姜重学金峰王凯
Owner NANJING YUANSHU MEDICAL TECH CO LTD
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