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Preparation method of (E)-1-aryl-4, 4, 4-trifluorobutyl-2-ene-1-one compound

A technology of ketone compound and trifluorobutane, which is applied in the field of compound preparation, can solve problems such as limited application, expensive reaction conditions, and harshness, and achieve low-cost effects

Active Publication Date: 2020-02-21
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods use relatively expensive reagents and relatively harsh reaction conditions, and sometimes metal reagents are also used, which greatly limits the application of such methods.

Method used

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  • Preparation method of (E)-1-aryl-4, 4, 4-trifluorobutyl-2-ene-1-one compound
  • Preparation method of (E)-1-aryl-4, 4, 4-trifluorobutyl-2-ene-1-one compound
  • Preparation method of (E)-1-aryl-4, 4, 4-trifluorobutyl-2-ene-1-one compound

Examples

Experimental program
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Effect test

Embodiment 1

[0055] Preparation of (E)-1-phenyl-4,4,4-trifluorobut-2-en-1-one (compound 1)

[0056] At room temperature, add 334 mg (1.0 mmol) of 4-phenyl-2-trifluoromethanesulfonyl-1,1,1-trifluoro-2-butene, anhydrous solvent 4 mL of 1,2-dichloroethane, 4-methylpyridine-N- Oxide 218mg (2.0mmol), 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene 1.0 times molar amount of triethylamine 101mg (1.0mmol), placed React at 25°C for 3 hours. After the solvent was removed by rotary evaporation under reduced pressure, the target compound was obtained by column chromatography, the filler was silica gel, the eluent was petroleum ether, and the separation yield was 81%.

Embodiment 2

[0058] Preparation of (E)-1-(4-methylphenyl)-4,4,4-trifluorobut-2-en-1-one (compound 2)

[0059] In addition to replacing the 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene in Example 1 with the same molar amount of 4-(4-methylphenyl) Except for -2-trifluoromethanesulfonyl-1,1,1-trifluoro-2-butene, the same method as in Example 1 was followed to obtain the target compound with an isolated yield of 84%.

Embodiment 3

[0061] Preparation of (E)-1-(3-methylphenyl)-4,4,4-trifluorobut-2-en-1-one (compound 3)

[0062] In addition to changing the 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene in Example 1 to the same molar amount of 4-(3-methylphenyl) Except for -2-trifluoromethanesulfonyl-1,1,1-trifluoro-2-butene, the same method as in Example 1 was followed to obtain the target compound with an isolated yield of 82%.

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Abstract

The invention discloses a preparation method of an (E)-1-aryl-4, 4, 4-trifluorobutyl-2-ene-1-one compound, and belongs to the field of compound preparation. The (E)-1-aryl-4, 4, 4-trifluorobutyl-2-ene-1-one compound is prepared by taking a compound shown in general formula II as a raw material and reacting according to a reaction formula disclosed in the invention in the presence of an oxidizing agent and an alkali to obtain a compound shown as general formula I. According to the method, compounds which are low in cost, and easily and widely available are taken as the oxidizing agent and the alkali, so that the convenient low-cost method is provided for synthesis of the (E)-1-aryl-4, 4, 4-trifluorobutyl-2-ene-1-one compound; and using of expensive and unstable trifluoromethylation reagentsand metal reagents is avoided.

Description

technical field [0001] The invention relates to a preparation method of (E)-1-aryl-4,4,4-trifluorobut-2-en-1-one compound, which belongs to the field of compound preparation. Background technique [0002] It is well known that due to the special properties of fluorine element, the introduction of CF into organic molecules 3 Can significantly change the physical, chemical and biological properties of molecules (Chem. Rev. 2016, 116, 422). Therefore, fluorine-containing compounds have important applications in the fields of medicine, agriculture and materials. (E)-1-aryl-4,4,4-trifluorobut-2-en-1-one compounds are important reaction intermediates in organic synthesis reactions and important building blocks for the synthesis of trifluoromethyl-containing compounds. New trifluoromethyl-containing active molecules can be constructed through various reactions. For example, it can be applied to Michael addition reaction (Org.Lett.2017,19,5102), Friedel-Crafts reaction (Chem.Eur....

Claims

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Application Information

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IPC IPC(8): C07C45/28C07C49/80C07C49/813C07C253/30C07C255/56C07D333/22
CPCC07B2200/09C07C45/28C07C253/30C07D333/22C07C49/80C07C49/813C07C255/56
Inventor 周宇涵李栋吕树均曲景平
Owner DALIAN UNIV OF TECH
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