A kind of alkynyl sulfone compound and its preparation method and application

A compound, the technology of alkynyl sulfone, which is applied in the field of alkynyl sulfone compounds and their preparation, can solve the problems of cumbersome steps and harsh conditions, and achieve the effect of simple operation, simple steps and high yield

Active Publication Date: 2022-04-12
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the embodiments of the present invention is to provide an alkynyl sulfone compound to solve the problems of harsh conditions and cumbersome steps in the preparation of the existing alkynyl sulfone compounds proposed in the background art

Method used

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  • A kind of alkynyl sulfone compound and its preparation method and application
  • A kind of alkynyl sulfone compound and its preparation method and application
  • A kind of alkynyl sulfone compound and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0044] An alkynyl sulfone compound, the specific structural formula is:

[0045]

[0046] In this example, the specific synthesis steps of the alkynyl sulfone compound with the above structure are as follows:

[0047] Add phenylacetylene (0.3mmol), sodium p-toluenesulfinate (0.9mmol), KI (1.0 equivalent), H 2 O (0.1 mL) and CH 3 CN (10.0mL) was mixed to obtain a mixture. A three-necked flask was equipped with a platinum electrode (1.0cm×1.0cm×0.2mm) as an anode and a cathode. The mixture was stirred and electrolyzed at a constant current of 10mA at room temperature for 7h. After the reaction was completed, the reaction The system was transferred to a 25mL eggplant-shaped bottle, and the Heidolph rotary evaporator (80-100rpm, temperature 38°C, vacuum 0.1Mpa) was used for rotary evaporation treatment for 3min, and the residue was subjected to column chromatography with 200 mesh silica gel. Chromatography (the developer of column chromatography is sherwood oil and ethyl acet...

Embodiment 2

[0052] An alkynyl sulfone compound, the specific structural formula is:

[0053]

[0054] In this example, the specific synthesis steps of the alkynyl sulfone compound with the above structure are as follows:

[0055] Add p-methoxyphenylacetylene (0.3mmol), sodium p-toluenesulfinate (0.9mmol), KI (1.0 equivalent ), H 2 O (0.1 mL) and CH 3 CN (10.0mL) was mixed to obtain a mixture. A three-necked flask was equipped with a platinum electrode (1.0cm×1.0cm×0.2mm) as an anode and a cathode. The mixture was stirred and electrolyzed at a constant current of 10mA at room temperature for 7h. After the reaction was completed, the reaction The system was transferred to a 25mL eggplant-shaped bottle, and the Heidolph rotary evaporator (80-100rpm, temperature 38°C, vacuum 0.1Mpa) was used for rotary evaporation treatment for 3min, and the residue was subjected to column chromatography with 200 mesh silica gel. Chromatography (the developer of column chromatography is sherwood oil and...

Embodiment 3

[0060] An alkynyl sulfone compound, the specific structural formula is:

[0061]

[0062] In this example, the specific synthesis steps of the alkynyl sulfone compound with the above structure are as follows:

[0063] Add phenylacetylene (0.3mmol), sodium p-tert-butylbenzenesulfinate (0.9mmol), KI (1.0 equivalent), H 2 O (0.1 mL) and CH 3 CN (10.0mL) was mixed to obtain a mixture. A three-necked flask was equipped with a platinum electrode (1.0cm×1.0cm×0.2mm) as an anode and a cathode. The mixture was stirred and electrolyzed at a constant current of 10mA at room temperature for 7h. After the reaction was completed, the reaction The system was transferred to a 25mL eggplant-shaped bottle, and the Heidolph rotary evaporator (80-100rpm, temperature 38°C, vacuum 0.1Mpa) was used for rotary evaporation treatment for 3min, and the residue was subjected to column chromatography with 200 mesh silica gel. Chromatography (the developer of column chromatography is sherwood oil and ...

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Abstract

The invention relates to the technical field of chemical synthesis, and specifically discloses an alkynyl sulfone compound and its preparation method and application. The alkynyl sulfone compound includes the following raw material alkyne compounds, sodium sulfinate compounds, potassium iodide, water and organic solvents. The alkynyl sulfone compounds provided by the present invention use alkyne compounds, sodium sulfinate compounds, potassium iodide, water and organic solvents as raw materials, and the alkynyl sulfone compounds can be prepared by electrolysis under mild metal-free catalyst conditions. Realize the synthesis of alkynyl sulfone compounds without high temperature, oxygen enrichment, constant pressure and other conditions, the reaction conditions are not harsh, and the steps are simple, no multi-step reaction is required, the synthesis steps are simplified, and the existing alkynyl sulfone compounds are solved. However, the preparation method of the alkynyl sulfone compound provided is simple in operation, high in yield and high in economic applicability.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to an alkynyl sulfone compound and its preparation method and application. Background technique [0002] Alkynyl sulfone compounds (alkynyl sulfone) are compounds obtained by modifying sulfones containing unsaturated C-C bonds, and can be converted into key intermediates of other heterocyclic compounds. They have various biological activities and photoconductivity. They are widely used in life sciences, It has a wide range of applications in the fields of organic synthesis and drug synthesis. [0003] Currently, there have been many reports on the synthesis of alkynyl sulfones, and efficient oxidative cross-coupling reactions involving terminal alkynes remain challenging. However, the preparation methods of alkynyl sulfone compounds in the prior art generally require the use of alkyl halides or alkynes as substrates, and the use of excess oxidants and metal splitting age...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/14C07C317/18C07C315/06C25B3/07C25B3/23
CPCC07C317/14C07C317/18C07C315/06C25B3/00
Inventor 孟祥太徐鹤华傅元媛王亚铭张颖茵陈登峰黄申林
Owner NANJING FORESTRY UNIV
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