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Alpha-chloro-alpha-fluoroalkyl sulfide derivative as well as synthesis method and application thereof

A technology of fluoroalkyl sulfide and synthesis method, applied in the field of α-chloro-α-fluoroalkyl sulfide derivatives and synthesis thereof, can solve problems such as difficult synthesis, achieve simple operation, high efficiency atom economy, The effect of simple and easy-to-obtain raw materials

Active Publication Date: 2021-03-02
PINGDINGSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because this kind of sulfur-fluorine products contains more functional groups, it is difficult to synthesize. Therefore, there is no report on the synthesis method of this kind of compounds with sulfur-containing and fluoroalkyl structures at the same time.

Method used

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  • Alpha-chloro-alpha-fluoroalkyl sulfide derivative as well as synthesis method and application thereof
  • Alpha-chloro-alpha-fluoroalkyl sulfide derivative as well as synthesis method and application thereof
  • Alpha-chloro-alpha-fluoroalkyl sulfide derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The α-chloro-α-fluoroalkyl sulfide derivative of the present invention has a structure as shown in formula (1):

[0033]

[0034] Among them, R 1 is phenyl, C 1 -C 10 Alkyl-substituted phenyl, halogen-substituted phenyl, hydroxyl-substituted phenyl, naphthyl, furyl, thienyl, benzyl, C 1 -C 10 Alkyl; X is sulfur, selenium; R 2 is a polyfluorinated alkyl group, a phosphate group, a C 1 -C 10 Alkyl substituted phosphate group, ester group, C 1 -C 10 Alkyl substituted ester, benzyl ester or phenylcarbonyl.

[0035] preferred, R 1 p-methylphenyl, p-chlorophenyl, p-bromophenyl, p-methoxyphenyl, p-hydroxyphenyl, 3,5-dichlorophenyl, 3,5-dimethylphenyl, m-bromo Phenyl, m-methoxyphenyl, o-methoxyphenyl, o-fluorophenyl, 2-naphthyl, 2-methyl-3-furyl, 2-thienyl, cyclohexyl, benzyl, methyl ester Propionate; R 2 is p-toluenesulfonyldifluoromethyl, trifluoromethyl, pentafluoroethyl, heptafluoropropyl, phenylcarbonyl, ethyl ester, benzyl ester or ethyl phosphate.

Embodiment 2

[0037]This example is a synthesis method of α-chloro-α-fluoroalkyl sulfide derivatives, using diazo compounds, diether compounds, and dichloroiodobenzene as raw materials, using organic solvents as solvents, and undergoing a one-step reaction , to obtain the α-chloro-α-fluoroalkyl sulfide derivatives shown in formula (1); the reaction process is shown in reaction formula (I):

[0038]

[0039] First, dissolve the diether compound and dichloroiodobenzene in the organic solvent to form a first mixed solution, then dissolve the diazo compound in the aforementioned organic solvent to form a second mixed solution, and then dissolve the first and second The mixed solutions are mixed and reacted to obtain the α-chloro-α-fluoroalkyl sulfide derivative represented by formula (4).

[0040] The molar ratio of the raw materials is diazo compound:diether compound:dichloroiodobenzene=(1.5-2.0):(0.8-1.0):(0.8-1.0).

Embodiment 3

[0042] The synthetic method of α-chloro-α-fluoroalkyl sulfide derivatives of this example is different from Example 2 in that the molar ratio of the raw materials is diazo compound: diether compound: dichloroiodobenzene =1.5:0.8:0.8.

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Abstract

The invention relates to an alpha-chloro-alpha-fluoroalkyl sulfide derivative as well as a synthesis method and an application thereof. The structural formula of the alpha-chloro-alpha-fluoroalkyl sulfide derivative is shown in the specification, wherein R1 is phenyl, C1-C10 alkyl substituted phenyl, halogen substituted phenyl, hydroxyl substituted phenyl, naphthyl, furyl, thienyl, benzyl or C1-C10 alkyl; X is sulfur or selenium; and R2 is a polyfluoro-substituted alkyl group, a phosphate group, a C1-C10 alkyl-substituted phosphate group, an ester group, a C1-C10 alkyl-substituted ester group,a benzyl ester group or a phenyl carbonyl group. According to the synthetic method of the alpha-chloro-alpha-fluoroalkyl sulfide derivative, diazo compounds, diether compounds and dichloroiodobenzeneare used as raw materials, an organic solvent is used as a solvent, and the alpha-chloro-alpha-fluoroalkyl sulfide derivative is obtained through a one-step reaction. The method has the advantages ofsimple and easily available raw materials, simplicity and convenience in operation, mild conditions, no need of metal catalysts, good substrate universality and the like. The obtained fluorine-containing organic compound has wide application in the fields of pesticides and medicinal chemistry.

Description

technical field [0001] The invention belongs to the field of synthetic medicine and chemical industry, and mainly relates to α-chloro-α-fluoroalkyl sulfide derivatives and their synthesis method and application. Background technique [0002] Fluorine-containing organic compounds are widely used in the fields of pesticide chemistry and medicinal chemistry. In addition, sulfur-containing organic compounds have good pharmaceutical activities such as antibacterial and anticancer in vivo, and are widely used in drug design. [0003] Drug molecules substituted with α-fluoroalkyl have attracted widespread attention due to their good biological activity. For example, the anti-AIDS drug DPC083 developed by Bristol-Myers Squibb is an organic small molecule substituted with α-fluoroalkyl. Another example is Wyeth The anti-cancer active small molecule Triazolopyrimidine developed by the company also contains an α-fluoroalkyl substitution structure. Therefore, as important synthetic int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/65C07D333/34C07D307/64C07D333/30C07D213/60C07C395/00C07C323/22C07C323/52C07C323/20C07F9/40
CPCC07C323/65C07C319/14C07D333/34C07D307/64C07D333/30C07D213/60C07C395/00C07C323/22C07C323/52C07C323/20C07F9/4075C07F9/4006C07C2601/14
Inventor 李玖零郑新华李彬夏西超王福安陈秋李钦贾欣宇陈娟王敏郭佳康杨玉洁
Owner PINGDINGSHAN UNIVERSITY