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Method for synthesizing asymmetric diaryl mono-selenide compound

A technology for a synthesis method of a diaryl monoselenide compound is applied in the field of synthesis of asymmetric diaryl monoselenide compounds, which can solve the problems of complex operation and poor functional group tolerance of the asymmetric diaryl monoselenide compound, and achieves simple and convenient operation. , the effect of high reaction efficiency and high yield

Inactive Publication Date: 2017-09-22
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0033] The first technical problem to be solved by the present invention is the problem of complex operation in the preparation process of asymmetric diaryl monoselenide compounds
[0034] The second technical problem to be solved by the present invention is the poor tolerance of functional groups in the preparation process of asymmetric diaryl monoselenide compounds
[0035] The third technical problem to be solved by the present invention is the problem that the preparation process of the asymmetric diaryl monoselenide compound is suitable for large-scale industrial production

Method used

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  • Method for synthesizing asymmetric diaryl mono-selenide compound
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  • Method for synthesizing asymmetric diaryl mono-selenide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Synthesis of (4-methoxy-2-nitrophenyl)(phenyl)selenoethers

[0082]

[0083] At room temperature, 2-nitro-4-methoxybenzoic acid (0.4mmol, 1equiv), elemental selenium (1.2mmol, 3equiv), iodobenzene (1.2mmol, 3equiv), Cu(OAc) 2 (0.04mmol), 1,10-phenanthroline (0.04mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL toluene join in the reaction tube, fill with oxygen then, and replace three times, under oxygen reaction environment, Stir at 100°C reaction temperature for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then ethyl acetate was added to filter, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether=98: 2), and the product was Yellow liquid, yield 95%, product weight 117mg.

[0084] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0085] 1 H NMR (500MHz, CDCl 3 ): δ7.80(d, J=2.8Hz, 1...

Embodiment 2

[0092] Synthesis of (5-methyl-2-nitrophenyl)phenyl selenide

[0093]

[0094] At room temperature, 5-methyl 2-nitrobenzoic acid (0.4mmol, 1equiv), elemental selenium (1.2mmol, 3equiv), iodobenzene (1.2mmol, 3equiv), Cu(OAc) 2 (0.04mmol), 1,10-phenanthroline (0.04mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL toluene join in the reaction tube, fill with oxygen then, and replace three times, under oxygen reaction environment, Stir at 100°C reaction temperature for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then ethyl acetate was added to filter, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether=98: 2), and the product was Yellow liquid, yield 90%, product weight 105mg.

[0095] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0096] 1 H NMR (500MHz, CDCl 3 ): δ8.20(d, J=8.4Hz, 1H), 7.7...

Embodiment 3

[0103] Synthesis of (2-nitro-4-trifluoromethylphenyl)phenylselenide

[0104]

[0105] At room temperature, 2-nitro-4-trifluoromethylbenzoic acid (0.4mmol, 1equiv), elemental selenium (1.2mmol, 3equiv), iodobenzene (1.2mmol, 3equiv), Cu(OAc) 2 (0.04mmol), 1,10-phenanthroline (0.04mmol), potassium carbonate (1.2mmol, 3equiv) and 2mL toluene join in the reaction tube, fill with oxygen then, and replace three times, under oxygen reaction environment, Stir at 100°C reaction temperature for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then ethyl acetate was added to filter, then the solvent was spun off, and the product was separated by column chromatography (eluent: petroleum ether: ether=98: 2), and the product was Yellow liquid, yield 85%, product weight 118mg.

[0106] The data of the proton nuclear magnetic resonance spectrum of gained product are as follows:

[0107] 1 H NMR (500MHz, CDCl 3 ): δ8.56(s, ...

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Abstract

The invention relates to a method for synthesizing an asymmetric diaryl mono-selenide compound. The method comprises the following steps: taking aryl carboxylic acid and aryl iodide as reaction materials under oxygen conditions in an organic solvent, taking elemental selenium as a selenium based reagent, carrying out a cascade reaction under the combined promotion action of a copper catalyst, a ligand and alkali, thereby obtaining the asymmetric diaryl mono-selenide compound. The method is cheap and readily available in aryl carboxylic acid substrate, aryl iodide and copper catalyst, wide in substrate range, simple in reaction conditions and high in product yield and purity, develops a novel synthetic route and method for the asymmetric diaryl mono-selenide compound and has excellent 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 synthesis method of an unsymmetrical diaryl monoselenide compound. Background technique [0002] So far, selenium has been widely used in the synthesis of medicine, polymer materials, and pesticides. For example, a number of drug molecules containing selenoether structures have been developed: Ebselen (Ebselen) was developed by Daiichi Pharmaceutical in Japan and Nattermann in Germany. A new type of anti-inflammatory drug, which is currently in clinical phase III research; selenium-containing tegafur phosphorothioate compounds with anti-tumor activity, selenium-modified southern Radix Radix polysaccharide compounds that have inhibitory effects on a variety of tumor cell lines . Even in the field of agriculture, the structure of selenide ether compounds exists in a wide spectrum of fungicides and herbicides, such as selenium-containing triazole am...

Claims

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Application Information

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IPC IPC(8): C07C391/02
CPCC07C391/02
Inventor 吴戈
Owner WENZHOU MEDICAL UNIV
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