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A kind of trifluoromethyl propenyl compound and its preparation method and application

A technology of trifluoromethylpropenyl and fluoromethylpropenyl, applied in the field of trifluoromethylpropenyl compounds and their preparation, can solve by-product halogen salt/high-salt wastewater, cumbersome post-reaction treatment, and reaction conditions Harsh problems, such as excellent stereoselectivity, tolerance to broad-spectrum functional groups, and low preparation cost

Active Publication Date: 2022-06-07
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The primary purpose of the present invention is to provide a method for preparing trifluoromethylpropenyl compounds, which aims to solve the problem of harsh reaction conditions, reliance on transition metal catalysis, cumbersome post-reaction treatment, and quantitative by-product halide salts in existing methods. / The problem of high salt wastewater

Method used

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  • A kind of trifluoromethyl propenyl compound and its preparation method and application
  • A kind of trifluoromethyl propenyl compound and its preparation method and application
  • A kind of trifluoromethyl propenyl compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) In a 10 mL Shrek tube, under an argon atmosphere, add 0.2 mmol of 2-hydroxy(phenyl) methyl methacrylate, 0.3 mmol of sodium trifluoromethanesulfinate, 0.008 mmol of 3,6,-di-tertiary Butyl-9-mesityl-10-phenylacridine-10-tetrafluoroborate, add 3mL of acetonitrile, stir the reaction under argon, room temperature and 18W blue light irradiation, the reaction equation is:

[0028]

[0029] (2) After the TLC monitoring reaction is complete, the solvent is removed with a vacuum rotary evaporator, the product is separated by thin layer chromatography, the developing solvent is petroleum ether / ethyl acetate system, and the product is a pale yellow liquid (E)-2-benzylidene -4,4,4-Methyl trifluorobutyrate, yield 71%.

[0030] (E)-2-benzylidene-4,4,4-trifluorobutyric acid methyl ester was subjected to nuclear magnetic resonance test, such as Figures 1 to 3 shown, figure 1 is the H NMR spectrum of (E)-2-benzylidene-4,4,4-trifluorobutyric acid methyl ester; figure 2 is the...

Embodiment 2

[0032] (1) In a 10 mL Shrek tube, under an argon atmosphere, add 0.4 mmol of 2-hydroxy(2,4-dichlorophenyl)methylcyclohex-2-en-1-one, 0.6 mmol of trifluoromethyl Sodium sulfinate, 0.016mmol 3,6,-di-tert-butyl-9-mesityl-10-phenylacridine-10-tetrafluoroborate, add 6mL acetonitrile, under argon, room temperature and 18W blue light The reaction is stirred under irradiation, and the reaction equation is:

[0033]

[0034] (2) after the TLC monitoring reaction is complete, the solvent is removed with a vacuum rotary evaporator, the product is separated by thin layer chromatography, and the developing agent is a petroleum ether / ethyl acetate system, and the product is a pale yellow liquid (E)-2-(2, 4-Dichlorobenzylidene)-3-(trifluoromethyl)cyclohexan-1 one, 74% yield.

Embodiment 3

[0036] This embodiment is basically the same as the above-mentioned embodiment 1, except that 10 mmol of 2-hydroxy(phenyl) methyl methacrylate, 15 mmol of sodium trifluoromethanesulfinate, 0.4 mmol of 3 ,6,-di-tert-butyl-9-mesityl-10-phenylacridine-10-tetrafluoroborate, add 150 mL of acetonitrile, stir the reaction under argon, room temperature and 18W blue light irradiation to obtain ( E) -2-benzylidene-4,4,4-trifluorobutyric acid methyl ester 1.76 g, yield 72%.

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Abstract

The invention discloses a trifluoromethylpropenyl compound, a preparation method and application thereof. The present invention directly uses allyl alcohol as raw material, selects CF 3 SO 2 Na is used as a trifluoromethylation reagent, using a metal-free and inexpensive photoredox catalyst, under the catalysis of an organic photoredox agent, the by-product SO is generated in situ 2 is repurposed to activate the C‑OH bond, allowing the reaction to occur in an environmentally friendly manner under mild conditions. The allyl alcohol used in the preparation method of the present invention is the MoritA-Baylis-Hillman alcohol allyl alcohol raw material with simple synthesis and high conversion rate, a wide range of applicable substrates, and low preparation cost; in addition, the preparation method of the present invention has simple steps, It has the characteristics of convenient operation, environmental protection, excellent stereoselectivity, and tolerance to broad-spectrum functional groups; the trifluoromethylpropenyl compound of the present invention is the preparation of related CF 3 Universal precursors of molecules with potential drug activity and biological activity can be widely used in biologically and pharmaceutically active molecules.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a trifluoromethylpropenyl compound and a preparation method and application thereof. Background technique [0002] The development of novel synthetic fluorination reactions has important implications in agriculture, medicine, and materials chemistry. Fluorine and fluoride-containing compounds can affect the properties of organic compounds, and their electronegativity, fully hydrophobic / lipophilic, and electrostatic interactions can significantly affect chemical reactions. Even a single fluorine atom can completely change the properties of a compound. [0003] Among them, fluorine-containing drugs have invested a lot of resources in academia and industry. Selective fluorination can intentionally improve drug properties, at least prolong the biological half-life of drugs by hindering oxidative metabolism, and increase bioabsorption through lipophilic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/343C07C69/65C07C45/68C07C49/697C07C67/14C07C69/54C07C69/732C07J9/00C07H13/04C07H1/00
CPCC07C67/343C07C69/65C07C45/68C07C49/697C07C67/14C07J9/00C07H13/04C07H1/00C07C2601/14C07C69/54C07C69/732
Inventor 解沛忠李博文
Owner NANJING TECH UNIV
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