Synthesis method of 2-phenylacetylene seleno alcohol compound

A synthetic method and technology of phenylacetylene, applied in the direction of organic chemistry, can solve the problems of poor functional group tolerance, pre-preparation, narrow substrate range, etc., and achieve the effects of simple post-processing, high yield and purity, and high reaction efficiency

Inactive Publication Date: 2021-01-22
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 2-phenylacetylene seleno alcohol compound
  • Synthesis method of 2-phenylacetylene seleno alcohol compound
  • Synthesis method of 2-phenylacetylene seleno alcohol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of 1-phenylacetylene selenyl-3-(4-methylphenoxy)-2-propanol compound

[0032]

[0033] At room temperature, phenylpropiolic acid (0.2mmol), elemental selenium (0.6mmol), 2-(4-methylphenoxy)methyloxirane (0.6mmol), copper chloride (0.02mmol) , 1,10-phenanthroline (0.02mmol), cesium carbonate (0.6mmol), tetrabutylammonium iodide (0.4mmol) and 2mL water, 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, yield ...

Embodiment 2

[0041] Synthesis of 1-phenylacetylene selenyl-3-(4-trifluoromethoxyphenoxy)-2-propanol compound

[0042]

[0043] At room temperature, phenylpropiolic acid (0.2mmol), elemental selenium (0.6mmol), 2-(4-trifluoromethoxyphenoxy)methyloxirane (0.6mmol), copper chloride ( 0.02mmol), 1,10-phenanthroline (0.02mmol), cesium carbonate (0.6mmol), tetrabutylammonium iodide (0.4mmol) and 2mL water, 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 ...

Embodiment 3

[0053] Synthesis of 1-phenylacetylene selenyl-3-(4-thiomethylphenoxy)-2-propanol compound

[0054]

[0055] At room temperature, phenylpropiolic acid (0.2mmol), elemental selenium (0.6mmol), 2-(4-thiomethylphenoxy)methyloxirane (0.6mmol), copper chloride (0.02mmol ), 1,10-phenanthroline (0.02mmol), cesium carbonate (0.6mmol), tetrabutylammonium iodide (0.4mmol) and 2mL water, 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 2-phenylacetylene seleno alcohol compound, which comprises the following steps: under air conditions, by using phenylpropiolic acid, selenium powder and an epoxy compound as reaction raw materials and water as a reaction solvent, carrying out cascade reaction under the joint promotion actions of a copper catalyst, a ligand, a phase transfer catalystand alkali to obtain the 2-phenylacetylene seleno alcohol compound. The method has the advantages of mild and simple reaction conditions, cheap and easily available substrate, and high yield and purity of the product, opens up a new synthetic route and method for the 2-phenylacetylene seleno alcohol 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 method for synthesizing 2-phenylacetylene selenol 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 selenylation o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/00C07D317/64
CPCC07C391/00C07D317/64
Inventor 吴戈姚渝静周雪莹
Owner WENZHOU MEDICAL UNIV
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