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2-trifluoroalkyl-1, 4-naphthoquinone compound and synthesis method thereof

A technology of trifluoroalkyl and synthesis method, which is applied in the field of 2-trifluoroalkyl-1,4-naphthoquinone compounds and their preparation, and achieves the effects of simple operation, low production cost and wide substrate range

Pending Publication Date: 2022-07-05
XINYANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • 2-trifluoroalkyl-1, 4-naphthoquinone compound and synthesis method thereof
  • 2-trifluoroalkyl-1, 4-naphthoquinone compound and synthesis method thereof
  • 2-trifluoroalkyl-1, 4-naphthoquinone compound and synthesis method thereof

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Embodiment 1

[0022] In a clean 10mL Schlenk pressure reaction tube, add 0.02mmol ferrous sulfate heptahydrate, 0.3mmol p-methylstyrene, 0.2mmol 2-phenylamino-1,4-naphthoquinone, 0.4mmol trifluoromethylidene in turn Sodium sulfonate, 0.5 mmol potassium persulfate, and 2 mL of acetonitrile were added as solvent, the reaction tube was replaced with nitrogen through a double-row tube, and then placed in an oil bath at 100° C. for heating and reaction for 20 hours. After the reaction, the acetonitrile was directly removed by a rotary evaporator, and the obtained residue was separated by a silica gel column using petroleum ether and ethyl acetate as eluents, and the obtained target product was a red solid. Characterization data are: 1 HNMR (600MHz, CDCl 3 ): δ[ppm]=8.10-8.08 (dd, J=7.7, 1.1Hz, 1H), 8.06-8.05 (dd, J=7.8, 1.2Hz, 1H), 7.74-7.71 (td, J=7.7, 1.1 Hz,1H),7.65-7.62(td,J=7.7,1.1Hz,1H),7.50(s,1H),7.22-7.19(t,J=7.8Hz,2H),7.14-7.12(t,J= 7.7Hz, 1H), 7.04-6.97(m, 6H), 4.14-4.12(t, J=7.1Hz,...

Embodiment 2

[0024] In a clean 10mL Schlenk pressure reaction tube, add 0.02mmol ferrous sulfate heptahydrate, 0.3mmol p-tert-butylstyrene, 0.2mmol 2-anilino-1,4-naphthoquinone, 0.4mmol trifluoromethyl in turn Sodium sulfinate, 0.5 mmol potassium persulfate, and 2 mL of acetonitrile were added as a solvent, the reaction tube was replaced with nitrogen through a double-row tube, and then placed in an oil bath at 100° C. for heating and reaction for 20 hours. After the reaction, the acetonitrile was directly removed by a rotary evaporator, and the obtained residue was separated by a silica gel column using petroleum ether and ethyl acetate as eluents, and the obtained target product was a red solid. Characterization data are: 1 H NMR (600MHz, CDCl 3 ): δ[ppm]=8.11-8.09 (dd, J=7.7, 1.1Hz, 1H), 8.07-8.05 (dd, J=7.7, 1.2Hz, 1H), 7.75-7.71 (td, J=7.7, 1.1 Hz,1H),7.65-7.62(td,J=7.8,1.2Hz,1H),7.48(s,1H),7.21-7.14(m,4H),7.11-7.09(t,J=7.7Hz,1H) ,7.01-6.97(m,4H),4.15-4.12(t,J=7.2Hz,1H),3.19-3.10(m...

Embodiment 3

[0026] In a clean 10mL Schlenk pressure reaction tube, add 0.02mmol ferrous sulfate heptahydrate, 0.3mmol p-acetoxystyrene, 0.2mmol 2-anilino-1,4-naphthoquinone, 0.4mmol trifluoromethyl in turn Sodium sulfinate, 0.5 mmol potassium persulfate, and 2 mL of acetonitrile were added as a solvent, the reaction tube was replaced with nitrogen through a double-row tube, and then placed in an oil bath at 100° C. for heating and reaction for 20 hours. After the reaction, the acetonitrile was directly removed by a rotary evaporator, and the obtained residue was separated by a silica gel column using petroleum ether and ethyl acetate as eluents, and the obtained target product was a red solid. Characterization data are: 1 H NMR (600MHz, CDCl 3 ): δ[ppm]=8.09-8.06(m, 2H), 7.75-7.73(td, J=7.7, 1.1Hz, 1H), 7.66-7.63(td, J=7.7, 1.2Hz, 1H), 7.57( s,1H),7.20-7.18(t,J=7.8Hz,2H),7.13-7.11(t,J=7.8Hz,1H),7.04-7.03(d,J=8.5Hz,2H),7.00-6.99 (d,J=8.5Hz,2H),6.89-6.87(d,J=8.6Hz,2H),4.11-4.09(t,J=7.1Hz,1...

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Abstract

The invention relates to a 2-trifluoroalkyl-1, 4-naphthoquinone compound and a synthesis method thereof, and the synthesis method specifically comprises the following steps: dispersing olefin with a structure (I), 1, 4-naphthoquinone with a structure (II), sodium trifluoromethanesulfinate with a structure (III), potassium persulfate and a catalyst in a solvent, and stirring and heating to construct a 2-trifluoroalkyl-1, 4-naphthoquinone target compound with a structure (IV). The invention provides a novel method for synthesizing a 2-trifluoroalkyl-1, 4-naphthoquinone compound by taking olefin, 1, 4-naphthoquinone and sodium trifluoromethanesulfinate as initial materials for reaction, iron salt as a catalyst and potassium persulfate as an oxidant for the first time. The substrate, the ferric salt catalyst and the potassium peroxodisulfate oxidant used in the method are low in price and easy to store, the method has the advantages of low production cost, simple operation, wide substrate range, product diversity and the like, and gram-scale preparation can be realized.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a 2-trifluoroalkyl-1,4-naphthoquinone compound and a preparation method thereof. Background technique [0002] Due to its large electronegativity and small atomic radius, the introduction of fluorine atoms into organic molecules usually changes the original physiological activity of the compound. Taking advantage of this feature, organic molecules containing fluorine, especially fluorine alkyl groups, are widely used in modern drug synthesis (ChemBioChem. 2004, 5, 557; J. Med. Chem. 2008, 51, 4359). In addition, 1,4-naphthoquinone and its derivatives can be used as an important active framework with bactericidal, anti-inflammatory, anti-cancer and other effects (Bioorg.Med.Chem.2009,17,634; Chem.Biodiversity 2014,11,341; J. Med. Chem. 2012, 55, 7273). Based on this idea, we combined the above two types of skeletons into one, aiming to develop a trifluoroalkyl-containing 1,4-na...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/30C07D221/08
CPCC07C221/00C07D221/08C07C225/30Y02P20/584
Inventor 唐林吕歌冷向宇
Owner XINYANG NORMAL UNIVERSITY
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