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A kind of preparation method of 1-aryl-3-azido-4,4,4-trifluoro-1-butene compound

A compound, azido-based technology, applied in the field of compound preparation, can solve problems such as limited application, expensive, unstable, etc., and achieve low-cost effects

Active Publication Date: 2019-08-20
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently synthesized containing CF 3 There are relatively few reports on substituted organic azides (J.Am.Chem.Soc.2003, 125, 6900.; Angew.Chem.Int.Ed.2014, 53, 1881.; ACS Catal.2015, 5, 2826. ; Org. Lett. 2014, 16, 3896.)
Moreover, these methods use the expensive, unstable CF 3 Methylation reagents, which greatly limit the application of such methods

Method used

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  • A kind of preparation method of 1-aryl-3-azido-4,4,4-trifluoro-1-butene compound
  • A kind of preparation method of 1-aryl-3-azido-4,4,4-trifluoro-1-butene compound
  • A kind of preparation method of 1-aryl-3-azido-4,4,4-trifluoro-1-butene compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Preparation of 1-phenyl-3-azido-4,4,4-trifluoro-1-butene (Compound 1)

[0056] At room temperature, add 167 mg (0.5 mmol) of 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene and anhydrous solvent to a 25mL Schlenk bottle protected by argon. Ethylene glycol dimethyl ether 5mL, 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene 1.2 times the molar amount of potassium bicarbonate 60mg (0.6mmol), 4 -Phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene 0.14mL (1.0mmol), 4-phenyl-2- 0.76 mL (10 mg / mL, 0.075 mmol) of triethylamine catalyst with 0.15 times molar amount of trifluoromethanesulfonate-1,1,1-trifluoro-2-butene was placed at 65°C for 12 hours of reaction. Extracted with ethyl acetate (3×10 mL), the combined organic phase was washed with saturated brine (2×10 mL) and dried over anhydrous magnesium sulfate. The target compound was obtained by column chromatography. The filler was silica gel and the eluent was petroleum. The ether separatio...

Embodiment 2

[0058] Preparation of 1-(4-methylphenyl)-3-azido-4,4,4-trifluoro-1-butene (Compound 2)

[0059] Except that 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene in Example 1 was replaced with the same molar amount of 4-(4-methylphenyl) Except for -2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene, the procedure was carried out in the same manner as in Example 1, and the target compound was obtained in an isolated yield of 69%.

Embodiment 3

[0061] Preparation of 1-(4-isopropylphenyl)-3-azido-4,4,4-trifluoro-1-butene (Compound 3)

[0062] Except that the 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene in Example 1 was replaced with the same molar amount of 4-(4-isopropylphenyl )-2-Trifluoromethanesulfonyl-1,1,1-trifluoro-2-butene was carried out in the same manner as in Example 1, and the target compound was obtained with an isolated yield of 77%.

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Abstract

The invention relates to a preparation method of a 1-aryl-3-azide-4,4,4-trifluoro-1-butene compound, and belongs to the technical field of compound preparation. According to the preparation method of the 1-aryl-3-azide-4,4,4-trifluoro-1-butene compound, the compound shown by a general formula I and azidotrimethylsilane are used as raw materials to take a reaction according to a following reaction formula under the existence of catalysts and additives so as to obtain the compound shown by the general formula I. The reaction formula is shown in the specification. The method provided by the invention has the advantages that the raw materials which have low cost and can be easily obtained in a wide range are used as catalysts; a convenient and low-cost method is provided for the synthesis of the 1-aryl-3-azide-4,4,4-trifluoro-1-butene compound; meanwhile, the use of expensive and instable trifluoromethylation reagents is avoided.

Description

Technical field [0001] The invention relates to a preparation method of a 1-aryl-3-azido-4,4,4-trifluoro-1-butene compound, which belongs to the field of compound preparation. Background technique [0002] Organic azide compounds are important reaction intermediates in organic synthesis reactions and important building blocks for the synthesis of nitrogen-containing compounds. For example, organic azide compounds can be converted into amines, isocyanates, and important nitrogen-containing heterocyclic structures in drug molecules (Chem. Eur. J. 2009, 15, 7830.; Angew. Chem. Int. Ed. 2005, 44, 5188. .). In recent years, in the field of click chemistry, copper-catalyzed cycloaddition reactions of organic azides and alkynes have also achieved a series of important results (Chem. Rev. 2009, 109, 5620.; Chem. Soc. Rev. 2010, 39, 1536.). At the same time, many organic azide compounds show good biological activities in antiviral and enzyme inhibitory effects (J. Med. Chem. 1993, 36, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C247/10C07D307/52
Inventor 周宇涵曲景平赵一龙张成海奚灏瀛董述祥范文霞
Owner DALIAN UNIV OF TECH
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