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
View PDF2 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap