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Preparation method of trans-stilbene compound

A technology of stilbene and compound, which is applied in the field of preparation of trans-stilbene compound, can solve the problems of complicated operation, poor functional group tolerance, etc., and achieves the effects of simple post-processing, simple and convenient operation, and simple post-processing operation.

Active Publication Date: 2018-10-16
WENZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Technical problem: the first technical problem to be solved by the present invention is the problem of complex operation in the preparation process of trans-stilbene compounds
[0007] The second technical problem to be solved by the present invention is the poor tolerance of functional groups in the preparation process of trans-stilbene compounds
[0008] The third technical problem to be solved by the present invention is the problem of configuration selection in the preparation process of trans-stilbene compounds

Method used

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  • Preparation method of trans-stilbene compound
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  • Preparation method of trans-stilbene compound

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preparation example Construction

[0044] A kind of preparation method of trans-stilbene compound, in organic solvent, under nitrogen or inert gas condition, with toluene acetylene having the structure shown in formula (I) as reaction substrate, in the common of alkali and elemental selenium Under the action of promotion, the carbon-carbon triple bond in the tolanne structure is chemoselectively reduced to obtain a reaction solution, and the reaction solution is post-treated to obtain trans-stilbene with the structure shown in formula (II).

[0045] Above-mentioned reaction process, available following reaction equation expression:

[0046]

[0047] (1) alkali

[0048] The alkali selected in the present invention is at least one of potassium carbonate, potassium acetate, sodium acetate, lithium acetate, sodium bicarbonate, ammonium acetate, calcium acetate, zinc acetate, barium acetate, silver acetate, preferably potassium acetate;

[0049] In terms of molar weight, the ratio of the amount of the base to th...

Embodiment 1

[0068] Synthesis of (E)-1,2-stilbene

[0069]

[0070] At room temperature, (E)-1,2 tolanylacetylene (0.4mmol, 1equiv), selenium powder (1.2mmol, 3equiv) and potassium acetate (KOAc) (0.8mmol, 2equiv) were added to the reaction tube, and then Gas-nitrogen replacement three times, add 12.4mmol N, N-dimethylformamide (DMF), stir at 150 ° C reaction temperature for 24h, after the reaction is monitored by thin layer chromatography, the reaction liquid is cooled, and then the reaction liquid Post-processing is to obtain (E)-1,2-stilbene.

[0071] Postprocessing includes the following steps:

[0072] Add ethyl acetate to the reaction solution for dilution, and concentrate under reduced pressure to obtain a concentrate, wherein: the volume ratio of the reaction solution to ethyl acetate is 1:5;

[0073] The concentrate was separated by column chromatography to obtain an eluate in which:

[0074] The silica gel separated by column chromatography is 300-400 mesh silica gel;

[0...

Embodiment 2

[0082] Synthesis of (E)-4-Styrylbenzaldehyde

[0083]

[0084] At room temperature, (E)-4-phenylethynyl benzaldehyde (0.4mmol, 1equiv), selenium powder (0.4mmol, 1equiv) and KOAc (1.6mmol, 4equiv) were added to the reaction tube, then pumped-filled Nitrogen was replaced three times, 26 mmol dimethyl sulfoxide was added, and stirred at a reaction temperature of 160° C. for 12 h. After the end of the reaction is monitored by thin-layer chromatography, the reaction solution is cooled, and then the reaction solution is post-treated to obtain (E)-4-styryl benzaldehyde.

[0085] Postprocessing includes the following steps:

[0086] Add ethyl acetate to the reaction solution for dilution, and concentrate under reduced pressure to obtain a concentrate, wherein: the volume ratio of the reaction solution to ethyl acetate is 1:10;

[0087] The concentrate was separated by column chromatography to obtain an eluate in which:

[0088] The silica gel separated by column chromatography ...

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Abstract

The invention relates to a synthesis method of a trans-stilbene compound. In an atmosphere of nitrogen or inert gas and an organic solvent, diphenylacetylene serves as a reaction substrate, and the trans-stilbene compound is obtained through chemically selective reduction of the carbon-carbon triple bond in a diphenylacetylene structure by using elemental selenium and alkali. The raw material diphenylacetylene is easy to synthesize; the elemental selenium is cheap and easily available. The synthesis method of the trans-stilbene compound provided by the invention has the advantages of wide range of reaction substrate, high functional group tolerance, simple reaction conditions and high product yield and purity, provides good synthesis route and means for the trans-stilbene compounds, and has great application potential and research value.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a preparation method of a trans-stilbene compound. Background technique [0002] The traditional method of synthesizing trans-stilbene compounds is mainly catalyzed by some noble metals, such as palladium. [0003] At present, the hydrogenation reduction of olefins mainly relies on metal catalysts of heavy metals, including rhodium, ruthenium, iridium, and palladium. Expensive heavy metals not only cause high costs in the production process, but also require recycling of precious metal catalysts and catalysts after production is completed due to environmental reasons. Toxic metals in the production process. Furthermore, these rare metals are produced in small volumes each year and are facing rapidly depleting reserves, inhibiting industrial production. [0004] Due to the unique medicinal effects of trans-stilbene compounds, anti-senile dementia, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C5/09C07C15/52C07B53/00
CPCC07B53/00C07B2200/09C07C5/09C07C15/52
Inventor 刘妙昌安翠徐雨婷黄小波高文霞吴华悦
Owner WENZHOU UNIVERSITY
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