Calix[4]squaramide cyclohexanediamine derivative and method for catalyzing asymmetric Michael addition and acetalization tandem reaction by using derivative

A cyclohexanediamine, series reaction technology, applied in the field of catalytic organic synthesis, can solve the problems of low catalytic efficiency, difficult catalyst preparation, etc., and achieve the effects of high catalytic efficiency, mild synthesis process conditions, and broad industrial application prospects.
CN110283087AActive Publication Date: 2019-09-27CHANGZHOU UNIV
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
CHANGZHOU UNIV
Publication Date
2019-09-27

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Abstract

The invention belongs to the technical field of catalytic organic synthesis, and specifically relates to a calix[4]squaramide cyclohexanediamine derivative and a method for catalyzing an asymmetric Michael addition and acetalization tandem reaction by using the derivative. With an unsaturated keto ester and 1,3-dicarbonyl cycloketone as raw materials, the calix[4]squaramide cyclohexanediamine derivative as a catalyst, and dichloromethane as solvent, the Michael addition and acetalization tandem catalytic reaction is performed; after the reaction is finished, the solvent is concentrated and a product is obtained through separation by silica gel column chromatography. A calix[4]squaramide cyclohexanediamine catalyst involved in the invention is mild in synthesis process conditions, the separation of an intermediate is not needed, the catalytic efficiency is high, a relatively good ee value can be obtained by the catalytic reaction under the condition of room temperature, and broad application prospects are realized.
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Description

technical field

[0001] The invention belongs to the technical field of catalytic organic synthesis, and in particular relates to a calix[4] squaramide cyclohexanediamine derivative and its catalytic asymmetric Michael addition and acetalization series reaction method. Background technique

[0002] The Michael addition reaction of 1,3-dicarbonyl compounds with β,γ-unsaturated carbonyl compounds is a very important reaction in organic synthesis, and its products have biological and pharmaceutical activities. Unsaturated ketoesters are a class of multifunctional compounds containing carbon-carbon unsaturated bonds (alkenyl or alkynyl), ketone carbonyl and ester groups, and have high reactivity and unique reaction diversity in structure. With the continuous exploration and research of chemists, unsaturated ketoesters have been introduced into the series reaction, many new synthesis methods have been developed, and a large number of new heterocyclic compounds have been created. ...

Claims

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