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Synthesis method of 1-arylacetylene seleno-3-phenoxy-2-propanol compound

A synthesis method and phenoxy technology, applied in the field of organic compound synthesis, can solve the problems of pre-preparation, narrow substrate range, poor functional group tolerance, etc., and achieve the effects of simple post-processing, high yield and purity, and high yield

Inactive Publication Date: 2021-02-02
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these techniques provide an efficient synthetic route for the synthesis of alkynyl selenide compounds, most of these methods have many shortcomings such as the need to prepare raw materials in advance, the use of expensive silver oxidants, poor functional group tolerance, and narrow substrate range.

Method used

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  • Synthesis method of 1-arylacetylene seleno-3-phenoxy-2-propanol compound
  • Synthesis method of 1-arylacetylene seleno-3-phenoxy-2-propanol compound
  • Synthesis method of 1-arylacetylene seleno-3-phenoxy-2-propanol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of 1-(4-methylphenylacetylene selenyl)-3-phenoxy-2-propanol

[0032]

[0033] At room temperature, 4-methylphenylpropynoic acid (0.2mmol), elemental selenium (0.6mmol), phenyl glycidyl ether (0.6mmol), copper chloride (0.02mmol), 1,10-phenanthro Phenyl (0.02mmol), cesium carbonate (0.6mmol), tetrabutylammonium iodide (0.4mmol) and 2mL water were stirred at a reaction temperature of 50°C for 24h. After the reaction is over, add ethyl acetate to dilute, transfer the diluted solution to a separatory funnel for extraction, separate the aqueous phase and the organic phase, then extract the aqueous phase with ethyl acetate for 3 times, combine the organic phases, and add 5g of anhydrous sulfuric acid Sodium, stand still for 30min, wash the filter cake 3 times with 5mL ethyl acetate each time, then spin off the solvent, and obtain the product through column chromatography (eluent: sherwood oil: ethyl acetate=20: 1), the product is Light yellow solid with a meltin...

Embodiment 2

[0041] Synthesis of 1-(2,4,6-trimethylphenylethynylselenyl)-3-phenoxy-2-propanol

[0042]

[0043]At room temperature, 2,4,6-trimethylphenylpropynoic acid (0.2mmol), elemental selenium (0.6mmol), phenyl glycidyl ether (0.6mmol), copper chloride (0.02mmol), 1, 10-Phenanthroline (0.02mmol), cesium carbonate (0.6mmol), tetrabutylammonium iodide (0.4mmol) and 2mL water were stirred at a reaction temperature of 50°C for 24h. After the reaction is over, add ethyl acetate to dilute, transfer the diluted solution to a separatory funnel for extraction, separate the aqueous phase and the organic phase, then extract the aqueous phase with ethyl acetate for 3 times, combine the organic phases, and add 5g of anhydrous sulfuric acid Sodium, stand still for 30min, wash the filter cake 3 times with 5mL ethyl acetate each time, then spin off the solvent, and obtain the product through column chromatography (eluent: sherwood oil: ethyl acetate=20: 1), the product is Pale yellow liquid, yiel...

Embodiment 3

[0051] Synthesis of 1-(4-methoxyphenylacetylene selenyl)-3-phenoxy-2-propanol compound

[0052]

[0053] At room temperature, 4-methoxyphenylpropynoic acid (0.2mmol), elemental selenium (0.6mmol), phenyl glycidyl ether (0.6mmol), copper chloride (0.02mmol), 1,10-phenanthrene Roline (0.02mmol), cesium carbonate (0.6mmol), tetrabutylammonium iodide (0.4mmol) and 2mL water were stirred at a reaction temperature of 50°C for 24h. After the reaction is over, add ethyl acetate to dilute, transfer the diluted solution to a separatory funnel for extraction, separate the aqueous phase and the organic phase, then extract the aqueous phase with ethyl acetate for 3 times, combine the organic phases, and add 5g of anhydrous sulfuric acid Sodium, stand still for 30min, wash the filter cake 3 times with 5mL ethyl acetate each time, then spin off the solvent, and obtain the product through column chromatography (eluent: sherwood oil: ethyl acetate=20: 1), the product is Light yellow solid ...

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Abstract

The invention relates to a synthesis method of a 1-arylacetylene seleno-3-phenoxy-2-propanol compound. The method comprises the following steps of: under air conditions, reacting acetylenic acid, selenium powder and phenyl glycidyl ether as the reaction raw materials with water used as a reaction solvent under the joint promotion actions of a copper catalyst, a ligand, a phase transfer catalyst and alkali, and carrying out a cascade reaction to obtain the 1-arylacetylene seleno-3-phenoxy-2-propanol compound. The method has the advantages of mild and simple reaction conditions, cheap and easilyavailable substrate, and high yield and purity of the product, opens up a new synthetic route and method for the 1-arylacetylene seleno-3-phenoxy-2-propanol compound, and has good 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 1-arylacetylene selenyl-3-phenoxy-2-propanol compounds. Background technique [0002] As the core skeleton, alkynyl selenides widely exist in natural products with important biological activities, antibiotics, antioxidant drug molecules and candidate anticancer drugs. In addition, alkynyl selenide compounds can also undergo difunctionalization reactions to obtain multifunctional alkenyl selenide compounds, and through the later structural modification of their target products, it brings more possibilities for the discovery of innovative drugs. Therefore, exploring the efficient construction of alkynyl selenides from simple and easy-to-obtain raw materials has become one of the current research hotspots in organic chemistry, medicinal chemistry and materials science. Among them, transition metal copper catalyzed decarboxylation...

Claims

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Application Information

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IPC IPC(8): C07C391/00
CPCC07C391/00
Inventor 吴戈许亚玲周雪莹
Owner WENZHOU MEDICAL UNIV
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