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Application of L-tryptophane being taken as catalyst of Knoevenagel reaction

A tryptophan and catalyst technology, which is applied in the application field of L-tryptophan as a Knoevenagel reaction catalyst, can solve problems such as lack of versatility, and achieve the effects of strong versatility, low production cost and mild reaction conditions

Inactive Publication Date: 2012-03-21
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of this, the object of the present invention is to provide L-tryptophan as the application of Knoevenagel reaction catalyst, can solve the problem that existing Knoevenagel reaction catalyst lacks versatility, when carbonyl compound is aromatic aldehyde, heterocyclic aromatic aldehyde, aliphatic aldehyde or α, β-unsaturated aldehydes can achieve good catalytic effect; it can also solve the main problem that limits the wide application of Knoevenagel reaction at present, and can obtain the condensation product of carbonyl compound and 1,3-diketone compound; thus it is convenient for chemical work better application of the Knoevenagel reaction

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  • Application of L-tryptophane being taken as catalyst of Knoevenagel reaction
  • Application of L-tryptophane being taken as catalyst of Knoevenagel reaction
  • Application of L-tryptophane being taken as catalyst of Knoevenagel reaction

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Embodiment 1～30

[0013] Examples 1-30, Knoevenagel reaction catalyzed by L-tryptophan

[0014]

[0015] R 3 and R 4 electron-withdrawing group

[0016] General method: Add L-tryptophan (0.3mmol) to the reaction system containing carbonyl compound (1mmol), active methylene compound (1-2mmol) and DMSO (2mL), stir the reaction at room temperature, and use thin-layer chromatography method (GF254 silica gel plate) to monitor the reaction to the end, add dichloromethane (10mL) to dilute the reaction solution, wash with water 2 times (5ml each time) to remove L-tryptophan, and extract the water washing solution 2 times with dichloromethane (each time 10mL), the organic layers were combined, washed with water (30mL), and the solvent was distilled off under reduced pressure to obtain the crude condensation product, which was subjected to flash column chromatography (the stationary phase was 200-300 mesh silica gel, and the mobile phase was a mixture of ethyl acetate and petroleum ether). liquid) ...

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Abstract

The invention discloses an application of L-tryptophane being taken as catalyst of Knoevenagel reaction. The invention has the advantages of strong universality, high catalysis efficiency, mild reaction condition, high product yield, low production coast and safety and innocuity and also can obtain condensation product of carbonyl compound and 1, 3-deketone compound, and the invention has favourable application prospect.

Description

technical field [0001] The present invention relates to a new application of compounds, in particular to the application of L-tryptophan as a Knoevenagel (Knoevenagel) reaction catalyst. Background technique [0002] The Knoevenagel reaction is a condensation reaction between carbonyl compounds and active methylene compounds. It is an important method for forming carbon-carbon double bonds in organic synthesis. It has been highly valued and widely used for a long time, and has become a classic reaction in organic chemistry. . Catalysts commonly used in the Knoevenagel reaction include bases, Lewis acids, zeolites, and heterogeneous catalysts, but these catalysts lack versatility. When the carbonyl compound is an aromatic aldehyde, a better catalytic effect can be achieved. When the carbonyl compound is an aliphatic aldehyde or α , β-unsaturated aldehydes have poor catalytic effect. [0003] In addition, the main problem that currently limits the wide application of the Kno...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/217C07C67/343C07C69/738C07D307/54C07C49/235C07C49/203C07C49/255B01J31/04C07C255/56C07C255/57C07C45/74C07C253/30C07D307/46C07B37/00
Inventor 官智何延红胡颖
Owner SOUTHWEST UNIV