Preparation method of 1-aryl-3-azide-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, instability, and high cost, and achieve low-cost effects

Active Publication Date: 2017-11-24
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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  • Preparation method of 1-aryl-3-azide-4,4,4-trifluoro-1-butene compound
  • Preparation method of 1-aryl-3-azide-4,4,4-trifluoro-1-butene compound
  • Preparation method of 1-aryl-3-azide-4,4,4-trifluoro-1-butene compound

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Experimental program
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Effect test

Embodiment 1

[0054] Preparation of 1-phenyl-3-azido-4,4,4-trifluoro-1-butene (compound 1)

[0055] At room temperature, 167 mg (0.5 mmol) of 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene, anhydrous solvent, and 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 2-fold molar amount of trimethyl azide 0.14mL (1.0mmol), 4-phenyl-2- Trifluoromethanesulfonate-1,1,1-trifluoro-2-butene 0.15 times molar amount of triethylamine catalyst 0.76mL (10mg / mL, 0.075mmol), placed at 65°C for 12 hours. Extracted with ethyl acetate (3×10mL), the combined organic phase was washed with saturated brine (2×10mL) 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 isolation yield was 90%.

Embodiment 2

[0057] Preparation of 1-(4-methylphenyl)-3-azido-4,4,4-trifluoro-1-butene (compound 2)

[0058] Except that the 4-phenyl-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene in Example 1 is replaced by 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 69%.

Embodiment 3

[0060] Preparation of 1-(4-isopropylphenyl)-3-azido-4,4,4-trifluoro-1-butene (compound 3)

[0061] 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-(4-isopropylphenyl )-2-trifluoromethanesulfonate-1,1,1-trifluoro-2-butene, the same method as in Example 1 was carried out to obtain the target compound 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 1-aryl-3-azido-4,4,4-trifluoro-1-butene compound, which belongs to the field of compound preparation. Background technique [0002] Organic azides are important reaction intermediates in organic synthesis reactions and important building blocks for the synthesis of nitrogen-containing compounds. For example, organic azides 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 have shown good biological activities in terms of antiviral and enzyme inhibitory effects (J.Med.Chem. 1993, 36, 2470.; Molecule...

Claims

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Application Information

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Patent Type & Authority Applications(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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