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1-(3-N-Substituted-carbazoly)-3-aryl-3-(2-oxocyclohexyl)-acetone and preparation method thereof

A cyclohexanone-based and carbazolyl-based technology, which is applied in the field of 1--3-aryl-3--acetone and its preparation, can solve the problems of strong alkali corrosion equipment and increased cost, and achieve low equipment requirements , fewer by-products, and mild reaction conditions

Inactive Publication Date: 2017-07-21
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are very few reports on Michael addition products containing carbazole groups, and most of them use strong bases as catalysts. Strong bases are easy to corrode equipment, resulting in increased costs.

Method used

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  • 1-(3-N-Substituted-carbazoly)-3-aryl-3-(2-oxocyclohexyl)-acetone and preparation method thereof
  • 1-(3-N-Substituted-carbazoly)-3-aryl-3-(2-oxocyclohexyl)-acetone and preparation method thereof
  • 1-(3-N-Substituted-carbazoly)-3-aryl-3-(2-oxocyclohexyl)-acetone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Sequentially weigh 0.006mol cyclohexanone, 0.006mol NaOH (solid, granular), and 30mL of absolute ethanol, and add them to a dry three-necked flask equipped with a condensing reflux tube and a stirring device, and let it stir at room temperature for 5 minutes. After uniformity, add 0.001mol of 1-(3-N-ethyl-carbazolyl)-3-(p-methoxyphenyl)-propenone, stir and slowly raise the temperature to 80°C, and make it Reflux reaction 40min under the temperature of 70rad / min stirring speed. During the reaction period, the reaction progress was monitored by thin-layer chromatography, and a developer with a volume ratio of V (ethyl acetate): V (petroleum ether) = 1:3 was selected. After the reaction is complete, stop the reaction, let the reaction system drop to room temperature slowly, add 30mL of 3°C cold water, let it stand still, a solid precipitates, filter with suction, wash the filter cake repeatedly until it is neutral, recrystallize it with absolute ethanol, and evaporate it w...

Embodiment 2

[0047] Sequentially weigh 0.006mol cyclohexanone, 0.006mol NaOH (solid, granular), and 30mL of absolute ethanol, and add them to a dry three-necked flask equipped with a condensing reflux tube and a stirring device, and let it stir at room temperature for 5 minutes. After uniformity, add 0.001mol 1-(3-N-ethyl-carbazolyl)-3-(2-thienyl)-propenone, stir and slowly raise the temperature to 70°C, make it at 70°C and Reflux reaction for 30min at a stirring speed of 70rad / min. During the reaction period, the reaction progress was monitored by thin-layer chromatography, and a developer with a volume ratio of V (ethyl acetate): V (petroleum ether) = 1:3 was selected. After the reaction is complete, stop the reaction, let the reaction system drop to room temperature slowly, add 30mL of 3°C cold water, let it stand still, a solid precipitates, filter with suction, wash the filter cake repeatedly until it is neutral, recrystallize it with absolute ethanol, and evaporate it with a rotary e...

Embodiment 3

[0052] Weigh 0.006mol cyclohexanone, 0.006mol NaOH (solid, granular), and 30mL of absolute ethanol into a dry three-necked flask equipped with a condensing reflux tube and a stirring device, and stir at room temperature for 5 minutes. After mixing evenly, add 0.001mol of 1-(3-N-methyl-carbazolyl)-3-(p-methylphenyl)-propenone, stir and slowly raise the temperature to 80°C, and make it Reflux reaction 75min under the temperature of 70rad / min stirring speed. During the reaction period, the reaction progress was monitored by thin-layer chromatography, and a developer with a volume ratio of V (ethyl acetate): V (petroleum ether) = 1:3 was selected. After the reaction is complete, stop the reaction, let the reaction system drop to room temperature slowly, add 30mL of 3°C cold water, let it stand still, a solid precipitates, filter with suction, wash the filter cake repeatedly until it is neutral, recrystallize it with absolute ethanol, and evaporate it with a rotary evaporator. Rem...

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Abstract

The invention discloses 1-(3-N-substituted-carbazoly)-3-aryl-3-(2-oxocyclohexyl)-acetone and a preparation method thereof; the 1-(3-N-substituted-carbazoly)-3-aryl-3-(2-oxocyclohexyl)-acetone has a structural formula shown in the description; the preparation method comprises: adding 1-(3-N-substituted-carbozoyl)-3-acryl-acetone, NaOH, acetone and absolute ethyl alcohol into a reaction container, stirring and heating for reflux reaction, adding suitable cold water after the reaction, standing for a period of time, when solid separates out, performing suction filtering, washing with water repeatedly until filter cakes are neutral, recrystallizing with absolute ethyl alcohol, evaporating with a rotary evaporator to remove the solvent, and drying in vacuum to obtain the target product. Sodium hydroxide is used herein as a catalyst, and the catalyst has good effect, low in price and easy to obtain; Liquid reflow process is adopted herein, the operation is simple, post-treatment is convenient, the yield is up to 94%, and the 1-(3-N-substituted-carbazoly)-3-aryl-3-(2-oxocyclohexyl)-acetone and the preparation method thereof have the advantages that reaction cavity is high, reaction speed is high, reaction time is short, the product has the properties, such as bacterial killing and inhibiting effects.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to 1-(3-N-substituted-carbazolyl)-3-aryl-3-(2-cyclohexanonyl)-acetone and a preparation method thereof. Background technique [0002] Carbazole is an important heterocyclic compound. First of all, it has a large conjugated system and strong electron transfer in the molecule. It has strong electron donating ability and hole transport ability, and thermal stability and photochemical stability. Higher stability; secondly, derivatives of carbazole compounds have potential wide applications in fields such as optoelectronic materials, dyes, medicine, supramolecular recognition, and chemical sensing. Its biological activity and medicinal significance have aroused the research interest of the majority of chemists. Azole compounds have been favored by researchers because of their broad application prospects in medicine (antibacterial, anticancer, antihistamine agents, antioxida...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D409/06C07D405/06A01P1/00A01P3/00A01P13/00A61P31/04A61P31/10
CPCC07D209/86C07D405/06C07D409/06
Inventor 刘玉婷王雨薇尹大伟辛宏乔倩瑜李洁刘一嘉
Owner SHAANXI UNIV OF SCI & TECH
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