Preparation method of 1, 4 enyne compound

A compound, enyne technology, applied in the field of organic chemical synthesis, can solve problems such as poor economy and unfriendly environment, and achieve the effects of convenient operation, low preparation cost and high atom economy
CN113548965AActive Publication Date: 2021-10-26NANJING UNIV OF TECH

Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
NANJING UNIV OF TECH
Publication Date
2021-10-26

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Abstract

The invention discloses a preparation method of a 1, 4 enyne compound, which comprises the following steps of in an inert gas atmosphere, adding allyl alcohol, acetylenic acid and a combined catalyst into an organic solvent, and stirring and reacting for 12-24 hours at the temperature of 80-100 DEG C to obtain a reaction solution, wherein the combined catalyst is prepared from organic palladium, villiaumite and cesium fluoride, and the villiaumite is bis (trifluoromethanesulfonimide) salt or bis (trifluoromethanesulfonate), and extracting the reaction solution by using water and ethyl acetate to remove part of the reaction solvent, drying and concentrating an organic phase, and purifying by using a petroleum ether / ethyl acetate developing solvent system through thin layer chromatography to obtain the 1, 4-eneyne compound. The preparation method is simple and convenient to operate, the obtained by-products only comprise water and carbon dioxide, and the method has the advantages of being high in atom economy and environmentally friendly; in addition, the preparation method is low in raw material price and wide in applicable substrate range.
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Description

technical field

[0001] The invention belongs to the field of organic chemical synthesis, in particular to a method for directly synthesizing 1,4-enyne compounds through dehydration and decarboxylation. Background technique

[0002] 1,4-Enynes are versatile reagents in organic synthesis and important structural motifs in natural products and bioactive compounds. In particular, 1,5-aryl disubstituted 1,4-enyne compounds show high drug activity. Among them, African potato (Hypoxis rooperi) can treat various diseases in traditional medicine, and its derivative rooperol is in Anti-inflammatory effects have been demonstrated in rodents in pharmacological studies. In addition, pharmacological studies in recent years have found that (E)-1-phenyl-5-methoxyphenyl-1-penten-4-yne has strong anticancer activity on the growth of human esophageal cancer cells. Therefore, the development of synthetic methods for 1,4-enyne compounds has aroused great concern in the synthetic community. ...

Claims

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