Method for preparing alpha-acyloxy ketone compound from terminal alkyne compounds

A technology of ketone compounds and acyloxy ketones, which is applied in the field of catalytic synthesis of α-acyloxy ketone compounds, can solve the problems of unreported acyloxylation and single reaction system, and achieve a good industrial The effect of application prospect, simple preparation, mild reaction process and easy control

Inactive Publication Date: 2017-08-04
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Terminal alkynes as acyloxylation reagents for α-acyloxylation of ketones have not been reported
And in these reactions, the reaction system is relatively simple (TBAI / TBHP)

Method used

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  • Method for preparing alpha-acyloxy ketone compound from terminal alkyne compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 0.4 mmol of propiophenone, 0.2 mmol of phenylacetylene, appropriate amount of tert-butanol peroxide, and 1 ml of chlorobenzene into the Schlenk tube under air environment, and add appropriate amount of catalyst (ferric chloride, copper bromide, copper acetate, copper chloride, ketone trifluoroacetate, copper nitrate, copper sulfate or copper acetylacetonate), at 120 o The reaction was stirred at C for 12 hours. By column chromatography, when copper acetylacetonate is used as a catalyst, the yield of the reaction can reach 70% yield.

Embodiment 2

[0030] Add 0.4 mmol of propiophenone, 0.2 mmol of phenylacetylene, an appropriate amount of copper acetylacetonate, and 1 ml of chlorobenzene into the Schlenk tube in the air environment, and add an appropriate amount of oxidants (tert-butanol peroxide, hydrogen peroxide, di-tert- Butyl peroxide, potassium persulfate complex salt), at 120 o The reaction was stirred at C for 12 hours. By column chromatography, when tert-butanol peroxide is used as the oxidant, the yield of the reaction can reach 70% yield.

Embodiment 3

[0032] Put 0.4 mmol of propiophenone, 0.2 mmol of phenylacetylene, an appropriate amount of copper acetylacetonate, and an appropriate amount of oxidant into the Schlenk tube under air environment, and add solvents (tetrahydrofuran, toluene, ethyl acetate, chlorobenzene, 1, 2-dichloroethane, acetonitrile, dimethyl sulfoxide, carbon tetrachloride), at 120 o The reaction was stirred at C for 12 hours. By column chromatography, when chlorobenzene is used as solvent, the yield of the reaction can reach 70% yield.

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Abstract

The invention provides a method for efficiently synthesizing an alpha-acyloxy ketone compound containing different substitute functional groups. According to the method, acetylacetone copper is taken as a reaction catalyst, t-butylhydroperoxide is taken as an antioxidant, ketone compounds and terminal alkyne compounds are taken as reaction substrates, and an organic solvent is added into a reaction system. The method has the advantages that the catalyst is cheap and easily available; reaction conditions are mild, safe and reliable; and the productivity of an obtained target product is relatively high. According to the method, the problem that a traditional alpha-acyloxylation reaction system is single is solved, and a novel acyloxylation reagent is provided; and the method has good industrial application prospects.

Description

technical field [0001] The present invention relates to the field of catalytic synthesis of α-acyloxy ketone compounds, in particular to a method for preparing α-acyloxy ketone derivatives by copper catalyzing ketone compounds and terminal alkyne compounds under the action of an oxidizing agent method. [0002] 【Background technique】 [0003] α-acyloxyketones are an important class of intermediates in organic synthetic chemistry. The hydrolyzed α-hydroxyketones have a wide range of physiological activities and can be applied to many natural products (terpenes and biological The synthesis of alkali) is a very important class of synthons; at the same time, it also exists in many natural products and active organic compounds, and it is a very important structural framework. Therefore, it is of great significance to study its synthetic methodology. [0004] With the development of organic synthesis methodology in recent years, great progress has been made in the synthesis of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/00C07C69/78C07C69/76C07C69/92C07C201/12C07C205/57C07C205/42C07D333/40C07D333/22C07C67/31C07B41/12
CPCC07B41/12C07C67/00C07C67/31C07C201/12C07D333/22C07D333/40C07C69/78C07C69/76C07C69/92C07C205/57C07C205/42
Inventor 周从山杨赞杨涛李姣
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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