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Method for synthesizing (E)-Alpha, Beta-unsaturated carbonyl compounds

A technology of carbonyl compounds and synthesis methods, applied in the field of catalytic organic synthesis, to achieve the effects of simple reaction conditions, green and environmentally friendly preparation process, and wide source of raw materials

Inactive Publication Date: 2009-10-28
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But this direct construction method requires ideally suitable catalysts

Method used

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  • Method for synthesizing (E)-Alpha, Beta-unsaturated carbonyl compounds
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  • Method for synthesizing (E)-Alpha, Beta-unsaturated carbonyl compounds

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preparation example 1

[0025] In a 50mL single-necked flask, add 0.01mmol organic bismuth ion compound (X=OSO 2 C 8 f 17 ) and 2.0mL water, 1.0mmol benzaldehyde (R 1 =Ph) and 1.0mmol n-propylamine (R 4 =n-C 3 h 7 ), after stirring for 5 minutes, add 1.2mmol cyclohexanone (R 2 -R 3 =-(CH 2 ) 4 -), placed in a water-bath reactor with magnetic stirring, and reacted at 25°C for 3 hours. TLC followed the reaction until the reaction was complete. The reaction result is: (E)-2-benzylcyclohexanone, the yield is 95%, and the selectivity of (E)-2-benzylcyclohexanone is 100%. After the catalyst was reused 10 times, its catalytic performance did not decrease.

preparation example 2

[0027] In a 50mL single-necked flask, add 0.03mmol organic bismuth ion compound (X=OSO 2 C 6 f 5 ) and 2.0mL water, 1.0mmol benzaldehyde (R 1 =Ph) and 1.0mmol n-propylamine (R 4 =n-C 3 h 7 ), after stirring for 5 minutes, add 1.2mmol acetophenone (R 2 = Ph, R 3 =H), placed in a water bath reactor with magnetic stirring, and reacted at 110° C. for 1 hour. TLC followed the reaction until the reaction was complete. The reaction result is: (E)-chalcone, the yield is 98%, and the selectivity of (E)-chalcone is 100%. After the catalyst was reused 5 times, its catalytic performance did not decrease.

preparation example 3

[0029] In a 50mL single-necked flask, add 0.05mmol organic bismuth ion compound (X=OSO 2 CF 3 ) and 2.0mL ethanol, 1.0mmol benzaldehyde (R 1 =Ph) and 1.0mmol n-propylamine (R 4 =n-C 3 h 7 ), after stirring for 5 minutes, add 1.2mmol acetone (R 2 =CH 3 , R 3 =H), placed in a water bath reactor with magnetic stirring, and reacted at 25° C. for 12 hours. TLC followed the reaction until the reaction was complete. The reaction result is: (E)-4-phenylbut-3-en-2-one, the yield is 100%, and the selectivity of (E)-2-benzylcyclohexanone is 100%. After the catalyst was reused 10 times, its catalytic performance did not decrease.

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Abstract

The invention provides a method for synthesizing (E)-Alpha, Beta-unsaturated carbonyl compounds, which takes aldehyde and ketone as raw materials, takes organic bismuth ion complexes containing bridged sulfur atom ligand as a main catalyst, takes aliphatic amine as an auxiliary catalyst, carries out a catalytic reaction in a protic solvent, thus preparing the (E)-Alpha, Beta-unsaturated carbonyl compounds. The synthesis method inaugurates a new low-cost and green approach for preparing the (E)-Alpha, Beta-unsaturated carbonyl compounds and has the advantages that the raw materials have wide source, the selectivity and the yield of the target outcome approach to 100%, the catalyst can be used repeatedly, the reaction condition is simple, the reaction is easy for operation, the cost is low and the preparation process is green and environment-friendly.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, in particular to a method for synthesizing (E)-α,β-unsaturated carbonyl compounds. 【Background technique】 [0002] α,β-Unsaturated carbonyl compounds are widely used in organic synthetic chemistry and biochemistry, for example, they can be used as reaction substrates for hydrogenation, peroxidation, cycloaddition, Michael addition, conjugate addition and other reactions. In terms of biological application, it can be used as the core unit of peroxidase proliferation diffuser-activated receptor γ, ligand. However, the construction of carbon-carbon double bonds in the synthesis of α,β-unsaturated carbonyl compounds still faces difficult challenges. The traditional carbon-carbon double bond construction method is obtained by Clayson-Schmidt condensation of aromatic aldehydes and aliphatic ketones under the catalysis of strong bases. This method uses strong bases, such as sodium hydroxide...

Claims

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Application Information

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IPC IPC(8): C07B37/02C07C49/683C07C49/796C07C49/794C07C49/697C07C49/753C07C49/647C07C49/217C07C45/74C07D307/46C07C69/618C07C67/343B01J31/22B01J31/02
CPCY02P20/584
Inventor 尹双凤邱仁华邱一苗张晓文许新华夏军
Owner HUNAN UNIV
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