Method for synthesizing 4-benzyl-5-hydroxy-1-phenyl-1-ene-3-ketone compound

Through the conjugated reduction-aldol addition tandem reaction catalyzed by non-precious metal Cu, the cumbersome steps and high cost problems in the synthesis of 4-benzyl-5-hydroxy-1-phenyl-1-ene-3-one compounds in the prior art are solved, and an efficient and low-cost synthesis method is achieved, which promotes the wide application of such compounds in more fields.

CN119707656AActive Publication Date: 2025-03-28DALIAN UNIV
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Patent Information

Application Number
CN202411871073.8
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-12-18
Publication Date
2025-03-28
Estimated Expiration
2044-12-18

AI Technical Summary

Technical Problem

The existing methods for synthesizing 4-benzyl-5-hydroxy-1-phenyl-1-enen-3-one compounds have problems such as cumbersome reaction steps, difficult raw materials to obtain, harsh reaction conditions and low yield, resulting in high production costs and limited industrial applications.

Method used

The cheap and easy-to-obenzyl acetone compounds, silanes and aldehydes are used as raw materials, and the conjugated reduction-aldol addition tandem reaction is carried out by catalytic reaction of non-precious metal Cu to produce 4-benzyl-5-hydroxy-1-phenyl-1-enen-3-one compounds. This method is carried out at room temperature, reducing the intermediate purification and separation steps of the reaction and making it easy to operate.

Benefits of technology

The efficient synthesis of 4-benzyl-5-hydroxy-1-phenyl-1-enen-3-one compounds under mild reaction conditions has been achieved, reducing production costs, improving production efficiency, and reducing environmental pollution.

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Abstract

The invention relates to the technical field of organic synthesis, and discloses a method for synthesizing a 4-benzyl-5-hydroxy-1-phenyl-1-ene-3-ketone compound, which comprises the following steps: under the catalysis of Cu, by taking silane as a reducing agent and organic phosphine as a ligand, carrying out conjugate reduction / aldol addition cascade reaction on a dibenzylidene acetone compound (I) and an aldehyde compound (II) to obtain the 4-benzyl-5-hydroxy-1-phenyl-1-ene-3-ketone compound. And carrying out a reaction to obtain the 4-benzyl-5-hydroxyl-1-phenyl-1-ene-3-ketone compound (III). According to the method, two-step cascade reaction is carried out in the same reaction container, reaction intermediates do not need to be separated, the operation processes of separation and purification are reduced, and the operation is simple and convenient. And the reaction conditions are mild and can be carried out at normal temperature. The catalyst copper is a non-noble metal catalyst and has the advantages of wide source, low price and the like.
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