Michael addition product of ferrocene-based chalcone and ethyl acetoacetate and preparation method thereof

A technology of ethyl acetoacetate and ethyl acetoacetate is applied in the field of preparing the Michael addition product of ferrocenyl chalcone and ethyl acetoacetate, which can solve the environmental pollution of organic solvents, long reflux reaction time and product purification. Trouble and other problems, to achieve the effect of less environmental pollution, convenience and easy operation, and short response time

Inactive Publication Date: 2014-08-20
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The Micheal addition reaction under traditional conditions is mostly obtained by reflux reaction in an organic solvent under the action of a strong base, but this method is often accompanied by many side reactions, such as the self-condensation of the substrate, rearrangement, and the formation of the addition prod

Method used

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  • Michael addition product of ferrocene-based chalcone and ethyl acetoacetate and preparation method thereof
  • Michael addition product of ferrocene-based chalcone and ethyl acetoacetate and preparation method thereof
  • Michael addition product of ferrocene-based chalcone and ethyl acetoacetate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 0.05 mol ferrocenylphenylchalcone ( be phenyl), 0.05mol ethyl acetoacetate and 0.0005mol sodium hydroxide, grind at room temperature until the raw material reacts completely, at this moment, TLC monitors and finds that the raw material point of ferrocenyl phenyl chalcone disappears (the developer of TLC is A mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3), then the product obtained by the reaction is washed with water, suction filtered, and the filter cake is recrystallized with water to obtain ferrocenyl phenyl chalcone and acetoacetic acid The Michael addition product of ethyl ester ( is phenyl), the yield is 91.3%, and the melting point is 178-185°C.

[0030] IR (KBr tablet): 3104cm -1 (Unsaturated C-H); 2922cm -1 ,2853cm -1 (saturated C-H); 1712cm -1 (-C=O-); 1596cm -1 、1573cm -1 、1494cm -1 (breathing vibration of benzene ring); 1375cm -1 、1456cm -1 (methyl and methylene); 718cm -1 、753cm -1 (monosubstituted benzene r...

Embodiment 2

[0033] Add 0.5 mol ferrocenyl-p-methylphenylchalcone ( be p-methylphenyl), 0.5mol ethyl acetoacetate and 0.006mol sodium hydroxide, grind at room temperature until the raw material reacts completely, at this time TLC monitors and finds that the raw material point of ferrocenyl p-methylphenylchalcone disappears (The developer of TLC is the mixed solvent of ethyl acetate and sherwood oil that the volume ratio is 1:3), then the product obtained by the reaction is washed with water, suction filtered, and the filter cake is recrystallized with water to obtain the ferrocenyl p-formaldehyde The Michael addition product of phenylchalcone and ethyl acetoacetate ( is p-methylphenyl), the yield is 92.4%, and the melting point is 178-183°C.

[0034] IR (KBr tablet): 3107cm -1 (Unsaturated C-H); 2989cm -1 ,2856cm -1 (saturated C-H); 1713cm -1 (-C=O-); 1587cm -1 、1513cm -1 、1451cm -1 (breathing vibration of benzene ring); 1375cm -1 、1443cm -1 (methyl and methylene); 819cm -1 (p...

Embodiment 3

[0037] Add 0.5 mol ferrocenyl p-methoxyphenylchalcone ( For p-methoxyphenyl), 0.5mol ethyl acetoacetate and 0.007mol sodium hydroxide, ground at room temperature until the raw material reacted completely, at this time TLC monitoring found the raw material of ferrocenyl p-methoxyphenyl chalcone point disappears (the developer of TLC is a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3), and then the product obtained by the reaction is washed with water, suction filtered, and the filter cake is recrystallized with water to obtain ferrocenyl The Michael addition product of p-methoxyphenylchalcone and ethyl acetoacetate ( is p-methoxyphenyl), the yield is 91.7%, and the melting point is 199-204°C.

[0038] IR (KBr tablet): 3149cm -1 (Unsaturated C-H); 2971cm -1 ,2831cm -1 (saturated C-H); 1712cm -1 (-C=O-); 1583cm -1 、1510cm -1 、1456cm -1 (breathing vibration of benzene ring); 1375cm -1 、1432cm -1 (methyl and methylene); 827cm -1 (para-po...

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Abstract

The invention provides a Michael addition product of ferrocene-based chalcone and ethyl acetoacetate and a preparation method thereof. The preparation method comprises the steps: adding A mol of ferrocene-based chalcone and B mol of ethyl acetoacetate into a dry reaction container, adding an alkaline substance as a catalyst, and grinding until the raw materials are subjected to complete reaction, wherein the ratio of A to B is 1:1; washing the product obtained from the reaction with water, carrying out suction filtration, recrystallizing the filter cake, and thus obtaining the Michael addition product of ferrocene-based chalcone and ethyl acetoacetate. The preparation method has the advantages of simple operation, short reaction time, mild reaction conditions, and low equipment requirements, the reaction is carried out only with grinding, at the same time, the catalyst is cheap and easy to get, the yield of the obtained product is up to 91.3% or more, the purity is high, and the preparation method is a green, simple and fast method for preparation of the Michael addition product of ferrocene-based chalcone and ethyl acetoacetate.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing a Michael addition product of ferrocenyl chalcone and ethyl acetoacetate. Background technique [0002] Chalcones are a class of natural organic compounds that exist in medicinal plants such as licorice and safflower. Due to their greater flexibility in molecular structure, they can bind to different receptors, so they have a wide range of biological activities, such as Antitumor, inhibit and clear oxygen free radicals, antibacterial, antiviral and other biological activities. In recent years, ferrocenylchalcone and its derivatives have been used as intermediates in organic synthesis, and their excellent properties have attracted more and more people's interest. [0003] Carbon-carbon bond condensation and corresponding functional group transformation are the most basic molecular reaction in organic synthesis, so the research on this aspect is gradually a...

Claims

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Application Information

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IPC IPC(8): C07F17/02
Inventor 刘玉婷刘蓓蓓尹大伟李均靖春燕杨阿宁
Owner SHAANXI UNIV OF SCI & TECH
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