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Preparation method of alpha, beta-diphenyl-1-aryl-acrylketone compound

A technology of diphenylcyclopropenone and arylpropenone, which is applied in the field of organic compound synthesis, can solve problems such as complicated operation and insufficiently mild reaction conditions, and achieve the effect of simple reaction operation, easy operation and high tolerance

Active Publication Date: 2017-11-24
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Purpose of the invention: the first technical problem to be solved by the present invention is the problem of complicated operation in the preparation process of α, β-diphenyl-1-phenylpropenone compound
[0009] The second technical problem to be solved by the present invention is the problem that the reaction conditions are not mild enough in the preparation process of α, β-diphenyl-1-phenylpropenone compound

Method used

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  • Preparation method of alpha, beta-diphenyl-1-aryl-acrylketone compound
  • Preparation method of alpha, beta-diphenyl-1-aryl-acrylketone compound
  • Preparation method of alpha, beta-diphenyl-1-aryl-acrylketone compound

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preparation example Construction

[0049] In the preparation method of the present invention, the reaction temperature is 0-30°C, non-limitingly, for example, it can be 0°C, 10°C, 20°C or 30°C

[0050] (6) Response time

[0051] In the preparation method of the present invention, the reaction time is not particularly limited. For example, the appropriate reaction time can be determined by detecting the residual percentage of the target product or raw material through liquid chromatography, which is usually 1-3 hours, non-limitingly for example 1 hour, 2 hours and 3 hours.

[0052] (7) Separation and purification

[0053] The mixture obtained after the reaction can be further separated and purified to obtain a purer final product. Those of ordinary skill in the art are familiar with the methods of separation and purification, for example, methods such as extraction, column chromatography, distillation, decantation, filtration, centrifugation, washing, evaporation, stripping and adsorption or a combination of a...

Embodiment 1

[0057]

[0058] At 30°C, 0.1mmol of diphenylcyclopropenone, 0.01mmol of Pd(PPh 3 ) 4 , 0.15mmol of phenylboronic acid was added to the reaction tube, and then pumped and filled with nitrogen three times. Under the nitrogen environment, 1ml of 1.4-dioxane was added, and the reaction was stirred at 30°C for 1 hour to obtain α, β-diphenyl- 1-Arylpropenone compounds.

[0059] Then add 10ml of ethyl acetate, then add silica gel powder, and obtain the product after separation by column chromatography (eluent: petroleum ether: ethyl acetate = 20:1), the product is a yellow solid, and the yield is 92%;

[0060] The proton nuclear magnetic resonance spectrum data of gained product are as follows:

[0061] 1 H NMR (500MHz, CDCl 3 )δ7.87-7.86(d,J=5.0Hz 2H),7.56-7.53(m,1H),7.46-7.43(m,2H),7.36-7.33(m,2H),7.29-7.28(m,2H ),7.24-7.17(m,4H),7.10-7.08(d,J=10.0Hz2H);

[0062] The carbon nuclear magnetic resonance spectrum data of gained product are as follows:

[0063] 13 C NMR (125M...

Embodiment 2

[0065]

[0066] At 0°C, 0.1 mmol of diphenylcyclopropenone, 0.001 mmol of PdCl 2 , 0.5mmol of 2-naphthylphenylboronic acid was added to the reaction tube, and then pumped and filled with nitrogen three times. Under nitrogen environment, 1ml of ethyl acetate was added and stirred at 0°C for 3 hours to obtain α,β-diphenyl-1 - arylpropenone compounds;

[0067] Then add 10ml of ethyl acetate, then add silica gel powder, and obtain the product after separation by column chromatography (eluent: petroleum ether: ethyl acetate = 20:1), the product is a white solid, and the yield is 89%;

[0068] The proton nuclear magnetic resonance spectrum data of gained product are as follows:

[0069] 1 H NMR (500MHz, CDCl 3 )δ8.38(s,1H),7.87-7.95(m,4H),7.51-7.60(m,2H),7.30-7.38(m,1H),7.15-7.24(m,3H),7.11(d, J=10.0Hz 2H);

[0070] The carbon nuclear magnetic resonance spectrum data of gained product are as follows:

[0071] 13 C NMR (125MHz, CDCl 3 )δ 197.5, 141.0, 139.9, 136.6, 135.5, ...

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Abstract

The invention belongs to the technical field of organic compound synthesis and particularly relates to a preparation method of an alpha, beta-diphenyl-1-aryl-acrylketone compound. According to the preparation method, in an organic solvent, diphenylcyclopropenone with structure as shown in a formula (I) and arylboronic acid with structure as shown in a formula (II) are taken as reaction materials, and the alpha, beta-diphenyl-1-aryl-acrylketone compound with structure as shown in a formula (III) is obtained through ring-opening reaction of cycolpropenone in the presence of a palladium catalyst; and in the formula (II) and the formula (III), R is independently selected from one of H, methyl, chlorine, trifluoromethyl, phenoxy, vinyl, fluorine, a formyl group, isopropyl, n-propyl, cyan, tertiary butyl, nitro or phenyl.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a preparation method of α,β-diphenyl-1-arylpropenone compound. Background technique [0002] Chalcone is an active substance that widely exists in plants in nature. Due to its greater flexibility and ability to bind to different receptors, it exhibits a broad spectrum of biological activities, such as anti-tumor, anti-virus, anti-bacterial, anti-inflammatory Wait. In addition, the α,β-enone structure has electrophilic activity, and is more inclined to interact with soft nucleophiles such as thiol compounds in the body, rather than interacting with hard nucleophiles such as amino groups and hydroxyl groups in nucleic acids, so as to avoid mutations or nucleophiles. Cancer, therefore, the safety of this type of structural compounds is relatively high. Therefore, it is of great significance to use chalcone as the lead compound for structural modifica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/06C07C45/45C07C49/796C07C49/84C07C49/813C07C49/86C07C201/12C07C205/45C07C253/30C07C255/56
CPCC07B41/06C07C45/45C07C201/12C07C253/30C07C49/796C07C49/84C07C49/813C07C49/86C07C205/45C07C255/56
Inventor 吴华悦单立冬徐雨婷刘妙昌黄小波高文霞
Owner WENZHOU UNIVERSITY
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