Alkyl alkyl sulfone compound as well as synthesis method and application thereof

A technology for the synthesis of alkyl alkyl sulfones, which is applied to the preparation of steroids, chemical instruments and methods, and organic compounds, and can solve the problems of poor substrate compatibility and heavy odor

Active Publication Date: 2020-08-11
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented process allows for direct construction of various types of chemical products through an intermediate product called alkyalkysulfoxides (AOS). These AOs are made by reacting different starting substances with each other at specific temperatures or pressures. By adding certain ingredients during this process, it becomes possible to create new ones without generating harmful waste material like ammonium hydrogen sulfonamide. Overall, these processes allow for efficient production of high purity chemically important intermediates such as alkoxyisopropanol derivatives used in perfume industry.

Problems solved by technology

This patented technical problem addressed by this patents relates to developing effective ways to make chemicals from unsaturated organosulfuranes (unsymmetrical polysulfanes) without requiring expensive or harmful substances like selenium dioxide).

Method used

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  • Alkyl alkyl sulfone compound as well as synthesis method and application thereof
  • Alkyl alkyl sulfone compound as well as synthesis method and application thereof
  • Alkyl alkyl sulfone compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of compound 3a:

[0033]

[0034] Under nitrogen protection, p-methylsulfonate compound 1a (0.2mmol), sodium metabisulfite (0.4mmol, 2.0equiv.), potassium formate (0.5mmol, 2.5equiv.), cesium carbonate (0.4mmol, 2.0equiv. ), tetrabutylammonium bromide (0.3mmol, 1.5equiv.), join in the reaction tube that is placed with magneton, add iodide n-butane (0.5mmol, 2.5equiv.), DMSO ( 2.0mL) the reaction system was heated to 100°C and reacted for 10 hours. After the p-toluenesulfonate alkyl ester was completely converted by pointing plate detection, the reaction system was cooled to room temperature, diluted with water and added ethyl acetate (10mL*3) Extracted, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain the purified target product 3a (77%) (PE / EA=10:1to 5:1, Rf=1 / 2). 1 H NMR (400MHz, CDCl 3 )δ7.09(d, J=8.8Hz, 2H), 6.84(d, J=8.4Hz, 2H), 3.79(s, 3H), 2.91(t, J=8.0Hz, 2H), 2.72(t, J=7.6Hz, 2H), 2.17...

Embodiment 2

[0036] Synthesis of compound 3b:

[0037]

[0038] Under nitrogen protection, p-methylsulfonate compound 1b (0.2mmol), sodium metabisulfite (0.4mmol, 2.0equiv.), potassium formate (0.5mmol, 2.5equiv.), cesium carbonate (0.4mmol, 2.0equiv. ), tetrabutylammonium bromide (0.3mmol, 1.5equiv.), join in the reaction tube that is placed with magneton, add iodide n-butane (0.5mmol, 2.5equiv.), DMSO ( 2.0mL) the reaction system was heated to 100°C and reacted for 10 hours. After the p-toluenesulfonate alkyl ester was completely converted by pointing plate detection, the reaction system was cooled to room temperature, diluted with water and added ethyl acetate (10mL*3) Extracted, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain the purified target product 3b (81%) (PE / EA=10:1to 5:1). 1 H NMR (400MHz, CDCl 3 )δ7.25-7.21(m,2H),7.19-7.08(m,3H),2.87-2.83(m,4H),2.71(t,J=7.4Hz,2H),2.14-2.06(m,2H) ,1.73-1.65(m,2H),1.43-1.32(m,2...

Embodiment 3

[0040] Synthesis of compound 3c:

[0041]

[0042] Under nitrogen protection, p-methylsulfonate compound 1c (0.2mmol), sodium metabisulfite (0.4mmol, 2.0equiv.), potassium formate (0.5mmol, 2.5equiv.), cesium carbonate (0.4mmol, 2.0equiv. ), tetrabutylammonium bromide (0.3mmol, 1.5equiv.), join in the reaction tube that is placed with magneton, add iodide n-butane (0.5mmol, 2.5equiv.), DMSO ( 2.0mL) the reaction system was heated to 100°C and reacted for 10 hours. After the p-toluenesulfonate alkyl ester was completely converted by pointing plate detection, the reaction system was cooled to room temperature, diluted with water and added ethyl acetate (10mL*3) Extracted, dried over anhydrous sodium sulfate, filtered, concentrated, and separated by column chromatography to obtain the purified target product 3c (78%) (PE / EA=10:1to 5:1, Rf=1 / 2). 1 H NMR (400MHz, CDCl 3 )δ7.24-7.18(m,2H),7.10-7.01(m,2H),2.97-2.91(m,4H),2.82(t,J=7.3Hz,2H),2.21-2.13(m,2H) ,1.82-1.74(m,2H),1.50-...

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Abstract

The invention discloses an alkyl alkyl sulfone compound as shown in a formula (1) (See the specification) and a synthesis method of a reagent as shown in a reaction formula (A) (See the specification). Alkyl p-methanesulfonate, an inorganic sulfur reagent and alkyl halide are used as reaction raw materials and react in a solvent under the action of alkali, a reducing agent and an additive to obtain a series of alkyl alkyl sulfone compounds. According to the invention, the alkyl alkyl sulfone compound is constructed in one step by taking an inorganic sulfur reagent as a sulfur dioxide source under a reduction condition, so that the defect of traditional synthesis of an alkyl alkyl sulfone compound through thioether oxidization is avoided; and the alkyl alkyl sulfone compound developed by the invention can successfully realize the connection of complex molecules.

Description

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Claims

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Application Information

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Owner EAST CHINA NORMAL UNIV
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