Preparation of 2-pimelie kelone compound

Abstract

The invention discloses a method for preparing 2-cyclohexenone compound, which comprises the following steps: under the action of a metallic catalyst MYn.L, 1, 6-heptadiyne compound showed in formula (I) taken as a raw material is reacted in an ionic liquid at a temperature of between 0 and 150 DEG C; after the reaction liquid is treated, the 2-cyclohexenone compound showed in formula (II) is prepared; and at the same time, the ionic liquid fixed with the metallic catalyst can be recycled. The method has the advantages of simple and reliable operation, high yield and selectivity, repeated recycling and use of the noble metal catalyst, environmental protection, and the like. Because the cyclohexenone compound is a good raw material for synthesizing medicines, pesticides and chemical products, the method has wide industrial application prospect.

Description

(1) Technical field [0001] The invention relates to a preparation method of 2-cyclohexenone compounds. (2) Background technology [0002] Cyclohexenone compounds are very important intermediates in organic synthesis and are used in the fields of medicine, pesticide and chemical industry. Although the synthetic method of multiple 2-cyclohexenone compounds is reported ((1) J.Heterocycl.chem.1972,9,741 at present; (2) J.Am.Chem.Soc.1976,98,4887 ; (3) J.Org.Chem.1977, 42, 1349; (4) Bull.Chem.Soc.Jap.1997, 79, 1879; (5) J.Org.Chem.1997, 62, 9323), but Due to the structural specificity of its functional derivatives, its synthesis is greatly restricted. For example, the synthesis of 4-substituted derivatives of 2-cyclohexenones needs to introduce substituents in advance before ring closure, and at least 4 ~5 steps of chemical reaction can be completed, and the synthesis of such compounds under alkaline conditions will be restricted if the starting material molecule has functional...

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Problems solved by technology

Although the synthetic method of multiple 2-cyclohexenone compounds is reported ((1) J.Heterocycl.chem.1972,9,741 at present; (2) J.Am.Chem.Soc.1976,98,4887 ; (3) J.Org.Chem.1977, 42, 1349; (4) Bull.Chem.Soc.Jap.1997, 79, 1879; (5) J.Org.Chem.1997, 62, 9323), but Due to the structural specificity of its functional derivatives, its synthesis is greatly restricted. For example, the synthesis of 4-substituted derivatives of 2-cyclohexenones needs to introduce substituents in advance before ring closure, and at least 4 ~5 steps of chemical reaction can be completed, and the synthesis of such compounds under alkaline conditions will be restricted if the starting material molecule has functional groups such as carbonyl

On this basis, there is a 1,6-heptadiyne compound and H 2 O under the catalysis of transition metal gold complex and protonic acid, the method of preparing 2-cyclohexenone compounds by hydration and intramolecular cyclization was reported (CN 1827577A; 2006), which skillfully solved the 4-position import substitution However, this method uses gold complexes as catalysts. Because the catalysts are expensive and cannot be recycled and reused, the reaction costs are increased and industrialized large-scale production is hindered.

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