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Acetylenic ketone derivative as well as preparation method and application thereof

A technology of derivatives and ketones, which is applied in the field of ketone derivatives and its preparation, can solve problems such as danger and inconvenient use, and achieve the effect of rich reactivity, simple and efficient synthesis

Pending Publication Date: 2020-05-15
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of transformation not only requires stoichiometric metal-organic reagents, but its use is inconvenient and dangerous;

Method used

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  • Acetylenic ketone derivative as well as preparation method and application thereof
  • Acetylenic ketone derivative as well as preparation method and application thereof
  • Acetylenic ketone derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] This embodiment carries out the preparation of 1-phenyl-3-(triisopropylsilyl)prop-2-yn-1-one (1a), and its reaction formula is as follows:

[0069]

[0070] Under a nitrogen atmosphere, 6.1 mg of ethylene glycol dimethyl ether nickel bromide, 4.7 mg of terpyridine, 5.8 mg of zinc chloride and 12.8 mg of zinc powder were successively added to the reactor, and the carboxylic acid shown in formula (II) was injected with a syringe. Thioester (0.2mmol), the solution of the mixed solvent (0.2mL / 0.2mL) of N,N-dimethylacetamide and tetrahydrofuran (0.2mL / 0.2mL) of alkynylation reagent (0.3mmol) shown in formula (III) is placed in the reactor React at room temperature for 24 hours, and the end of the reaction was confirmed by thin-layer chromatography analysis. The reaction solution was filtered through diatomaceous earth and then concentrated into dry powder with 400 mesh silica gel by rotary evaporation, and then the reaction product was separated by column chromatography. 4...

Embodiment 2

[0074] This embodiment carries out the preparation of 1-(3-methoxyphenyl)-3-phenylpropyl-2-yn-1-one (1b), and its reaction formula is as follows:

[0075]

[0076] Under a nitrogen atmosphere, 6.1 mg of ethylene glycol dimethyl ether nickel bromide, 4.7 mg of terpyridine, 5.8 mg of zinc chloride and 12.8 mg of zinc powder were successively added to the reactor, and the carboxylic acid shown in formula (II) was injected with a syringe. Thioester (0.2mmol), the solution of the mixed solvent (0.2mL / 0.2mL) of N,N-dimethylacetamide and tetrahydrofuran (0.2mL / 0.2mL) of alkynylation reagent (0.3mmol) shown in formula (III) is placed in the reactor React at room temperature for 24 hours, and the end of the reaction was confirmed by thin-layer chromatography analysis. The reaction solution was filtered through diatomaceous earth and then concentrated into dry powder with 400 mesh silica gel by rotary evaporation, and then the reaction product was separated by column chromatography. 4...

Embodiment 3

[0080] This embodiment carries out the preparation of 3-phenyl-1-(thiophen-2-yl)prop-2-yn-1-one (1c), and its reaction formula is as follows:

[0081]

[0082] Under a nitrogen atmosphere, 6.1 mg of ethylene glycol dimethyl ether nickel bromide, 4.7 mg of terpyridine, 5.8 mg of zinc chloride and 12.8 mg of zinc powder were successively added to the reactor, and the carboxylic acid shown in formula (II) was injected with a syringe. Thioester (0.2mmol), the solution of the mixed solvent (0.2mL / 0.2mL) of N,N-dimethylacetamide and tetrahydrofuran (0.2mL / 0.2mL) of alkynylation reagent (0.3mmol) shown in formula (III) is placed in the reactor React at room temperature for 24 hours, and the end of the reaction was confirmed by thin-layer chromatography analysis. The reaction solution was filtered through diatomaceous earth and then concentrated into dry powder with 400 mesh silica gel by rotary evaporation, and then the reaction product was separated by column chromatography. 400 m...

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses an acetylenic ketone derivative as well as a preparation method and application thereof. The structural formula of theacetylenic ketone derivative is shown as a formula (I), wherein R1 and R2 are respectively C1-C20 alkyl, halogen, ester group, carbonyl, nitro, substituted amino, C5-C30 aryl or C5-C30 aromatic heterocyclic group. Based on a nickel catalytic reduction coupling strategy, carboxylic acid derivatives widely existing in nature are used as substrates, alkynyl halide is taken as an active alkynylation reagent, and a universal and efficient method for rapidly constructing various different substituted acetylenic ketones at a room temperature is obtained. The acetylenic ketone compound not only can beused as a practical synthon, but also can be used as a precursor of heterocyclic compounds such as furan, pyrazole, quinoline and pyrimidine; the conversion also realizes the later-stage derivatization reaction of drugs such as ibuprofen, and is expected to obtain good application prospects in later-stage modification and development of new drugs and novel materials.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an acetylenone derivative and a preparation method and application thereof. Background technique [0002] The key to effectively constructing target molecules is to install, utilize, and transform and remove functional groups to achieve the desired complexity, and a powerful strategy to increase molecular complexity is to use a reagent that can transfer target functional groups. This strategy relies on reagents with sufficient activity to enhance the ability of the desired functional group to be transferred while maintaining its chemoselectivity. For the construction of target molecules with multiple active reaction sites, in view of their own good chemical activity, controlling the chemical activity and chemoselectivity of their reactions, including preventing excessive functionalization reactions, is also an issue that needs to be considered in the design ...

Claims

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Application Information

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IPC IPC(8): C07F7/08C07C45/56C07C49/84C07D333/22C07D307/46C07C49/813C07C49/794C07C49/223
CPCC07F7/081C07C45/562C07D333/22C07D307/46C07C49/84C07C49/813C07C49/794C07C49/223
Inventor 李先纬蔡晓清欧阳文森
Owner GUANGDONG UNIV OF TECH
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