A kind of β-fluoroalkyl cinnamate compound and preparation method thereof

A technology for cinnamate compounds and compounds is applied in the field of beta-fluoroalkyl cinnamate compounds and their preparation, which can solve the problems of side reactions, less selectivity and the like, and achieves the advantages of less side products, simple operation and easy preparation Effect

Active Publication Date: 2021-08-27
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Another object of the present invention is to provide a method for preparing the above-mentioned β-fluoroalkyl cinnamate compounds, aiming to solve the problems of less selectivity and side reactions in existing methods

Method used

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  • A kind of β-fluoroalkyl cinnamate compound and preparation method thereof
  • A kind of β-fluoroalkyl cinnamate compound and preparation method thereof
  • A kind of β-fluoroalkyl cinnamate compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] (1) Under nitrogen atmosphere, mix 0.1mmol benzyl 4-phenyl allenoate, 0.2mmol tetrafluoroborate 4-ethoxycarbonylphenyl diazonium salt, 1.0mmol triethylamine trihydrofluoride, 0.02mmol Ph 3 PAuCl was sequentially added to a reaction tube containing a mixed solvent of 0.3mL acetonitrile and 0.2mL 1,1-dichloroethane;

[0031] (2) Under nitrogen protection and room temperature, the reaction tube in which the reaction mixture was dissolved was irradiated under the blue light of 15W LED for 12 hours, and the reaction solution was filled with a column of 200-300 mesh silica gel, using ethyl acetate and The eluent with a volume ratio of petroleum ether of 10:90 was subjected to column separation to obtain pure β-fluoroalkyl cinnamate compound 1.

Embodiment 2

[0033] (1) Under nitrogen atmosphere, add 0.1mmol 4-phenyl allenoic acid phenyl ester, 0.2mmol tetrafluoroborate 4-ethoxycarbonylphenyl diazonium salt, 1.0mmol triethylamine trihydrofluoride, 0.02mmol Ph 3 PAuCl was sequentially added to a reaction tube containing a mixed solvent of 0.3 mL of acetonitrile and 0.2 mL of 1,1-dichloroethane.

[0034] (2) Under the protection of nitrogen and at room temperature, the reaction tube in which the reaction mixture was dissolved was irradiated under the blue light of 15W LED for 12 hours, and the reaction solution was filled with a column of 200-300 mesh silica gel, using ethyl acetate and petroleum The eluent with ether volume ratio of 10:90 was subjected to column separation to obtain β-fluoroalkyl cinnamate compound 2.

Embodiment 3

[0036] (1) Under nitrogen atmosphere, add 0.1mmol ethyl 4-phenyl allenoate, 0.2mmol tetrafluoroborate 4-ethoxycarbonylphenyl diazonium salt, 1.0mmol triethylamine trihydrofluoride, 0.02mmol Ph 3 PAuCl was sequentially added to a reaction tube containing a mixed solvent of 0.3 mL of acetonitrile and 0.2 mL of 1,1-dichloroethane.

[0037] (2) Under nitrogen protection and room temperature, the reaction tube in which the reaction mixture was dissolved was irradiated under the blue light of 15W LED for 12 hours, and the reaction solution was filled with a column of 200-300 mesh silica gel, using ethyl acetate and The eluent with a volume ratio of petroleum ether of 10:90 was subjected to column separation to obtain β-fluoroalkyl cinnamate compound 3.

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PUM

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Abstract

The present invention disclosed a β -fluorine cinnamite and its preparation method.By the invention, through the inert gas atmosphere, the plywide, nitrogen salt, trivial acetimelin salt, pH 3 PauCl is added to the hybrid solvent in turn to obtain a mixture; in an inert gas atmosphere, the mixture is placed in the wavelength of 450nm and a strength of 15W LED.In hour, the β -fluorine cinnamite compound is separated from the column layer analysis.The cost of raw materials required for the preparation method of the present invention is low, the corrosion of no glassware, mild response conditions, green and environmentally friendly, simple operation, and the functional groups of linked hydrane and gifted heavily nitrogen salt are widely compatible, and the response efficiency is high.It is convenient to separate. At the same time, the biggest advantage of this method is the product of the product, and there is no regional selective problem. This method can amplify the scale of the reaction and realize the grade preparation.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a β-fluoroalkyl cinnamate compound and a preparation method thereof. Background technique [0002] Fluorochemicals are widely used in the synthesis of natural products and pharmaceuticals. In recent decades, fluorine-containing compounds have received extensive attention from scientists and have made significant progress. With the continuous emergence and popularization of fluorine-containing reagents, it is very common to introduce fluorine atoms into compounds directly by constructing carbon-fluorine bonds. Strategy. However, the research on the addition strategy of fluorocarbon difunctionalization with the help of unsaturated compounds has only gradually emerged. Fluorine aromatization is one of the directions that needs to be developed urgently. The reported fluorine aromatization strategies mainly use oxidative electrophilic fluorine reagents....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/313C07C69/76C07D309/04C07C67/307C07C69/65C07C69/738C07C253/30C07C255/57C07C201/12C07C205/56
CPCC07C67/307C07C67/313C07C201/12C07C253/30C07D309/04C07C2601/10C07C2601/14C07C2601/18C07C69/76C07C69/65C07C69/738C07C255/57C07C205/56
Inventor 冯超唐海军
Owner NANJING TECH UNIV
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