CN114702399A - 2-trifluoroalkyl-1, 4-naphthoquinone compound and synthetic method thereof - Google Patents

2-trifluoroalkyl-1, 4-naphthoquinone compound and synthetic method thereof Download PDF

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CN114702399A
CN114702399A CN202210478856.4A CN202210478856A CN114702399A CN 114702399 A CN114702399 A CN 114702399A CN 202210478856 A CN202210478856 A CN 202210478856A CN 114702399 A CN114702399 A CN 114702399A
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naphthoquinone
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acetonitrile
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唐林
吕歌
冷向宇
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Xinyang Normal University
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    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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Abstract

A2-trifluoroalkyl-1, 4-naphthoquinone compound and a synthetic method thereof are disclosed, which comprises the following steps:
Figure DDA0003626814120000011
the alkene with the structure (I), the 1, 4-naphthoquinone with the structure (II), the sodium trifluoromethylsulfinate with the structure (III), the potassium persulfate and the catalyst are dispersed in a solvent, and the 2-trifluoroalkyl-1, 4-naphthoquinone target compound with the structure (IV) can be constructed by stirring and heating. The invention provides a novel method for synthesizing a 2-trifluoroalkyl-1, 4-naphthoquinone compound by taking olefin, 1, 4-naphthoquinone and sodium trifluoromethanesulfonate as reaction starting materials, taking iron salt as a catalyst and taking potassium persulfate as an oxidant for the first time. The substrate, iron salt catalyst and potassium persulfate oxygen used in the methodThe reagent has the advantages of low price, easy storage, low production cost, simple operation, wide substrate range, product diversity and the like, and can realize gram-scale preparation.

Description

2-trifluoroalkyl-1, 4-naphthoquinone compound and synthetic method thereof
Technical Field
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
Due to the characteristics of large electronegativity and small atomic radius, the introduction of fluorine atoms into organic molecules generally changes the original physiological activity of the compound. By utilizing this feature, organic molecules containing fluorine, especially fluoroalkyl groups, are widely used in modern drug synthesis (chem biochem.2004,5,557; j.med.chem.2008,51,4359). In addition, 1, 4-naphthoquinone and its derivatives can be used as an important active skeleton with bactericidal, anti-inflammatory and anti-cancer effects (bioorg.med.chem.2009,17,634; chem.biodiversity 2014,11, 341; j.med.chem.2012,55,7273). Based on the idea, the two skeletons are combined into one, and the aim is to develop the 1, 4-naphthoquinone compound containing the trifluoroalkyl. The currently reported synthesis methods of 2-trifluoroalkyl-1, 4-naphthoquinones are copper or silver catalyzed trifluoroalkylation of togni reagent with 1, 4-naphthoquinone, and these methods all require the use of expensive togni reagent as the trifluoromethyl source (org. lett.2013,15,3730; chem. commu.2013, 49,6614; j. org. chem.2019,84,1006). In addition, a synthesis method of visible light-induced 3-polyfluoroalkyl-2-amino-1, 4-naphthoquinone compounds is also reported (org. Lett.2021,23,519). The invention discloses a free radical coupling reaction among olefin, langliois reagent and 1, 4-naphthoquinone catalyzed by iron salt, and the method can prepare various 2-trifluoroalkyl-1, 4-naphthoquinone compounds by using cheap and easily-obtained iron salt and langliois reagent as a catalyst and a trifluoromethyl source respectively. The method has no relevant literature and patent report for a while.
Disclosure of Invention
The invention provides a novel method for synthesizing a 2-trifluoroalkyl-1, 4-naphthoquinone compound by taking olefin, 1, 4-naphthoquinone and sodium trifluoromethanesulfonate as initial materials for reaction, taking iron salt as a catalyst and taking potassium persulfate as an oxidant. In the method, potassium persulfate can oxidize sodium trifluoromethanesulfonate with one electron to form a trifluoromethyl free radical under the action of an iron catalyst, and then the potassium persulfate and alkene and 1, 4-naphthoquinone are subjected to free radical relay addition to provide a 2-trifluoroalkyl-1, 4-naphthoquinone product. The method uses cheap and easily-obtained olefin, 1, 4-naphthoquinone and sodium trifluoromethanesulfonate as reaction substrates, takes iron salt as a catalyst and takes potassium persulfate as an oxidant, and has the advantages of simple operation, wide substrate range, low price and the like.
The purpose of the invention is realized as follows:
Figure BDA0003626814100000021
dispersing olefin with a structure (I), 1, 4-naphthoquinone with a structure (II), sodium trifluoromethanesulfonate with a structure (III), potassium persulfate and a catalyst in a solvent, and heating by stirring to construct a 2-trifluoroalkyl-1, 4-naphthoquinone target compound with a structure (IV); wherein, the specific structure of IV is shown as follows
Figure BDA0003626814100000031
The catalyst is ferrous sulfate heptahydrate, ferric nitrate, ferric acetylacetonate, ferric chloride or ferric oxide;
the solvent can be acetonitrile, dichloromethane, 1, 2-dichloroethane, 1, 4-dioxane, tetrahydrofuran or ethyl acetate;
the reaction temperature is 100 ℃ to 140 ℃.
Has the advantages that: as a supplement to the existing synthesis method of 2-trifluoroalkyl-1, 4-naphthoquinone compounds, the invention provides a new synthesis method of 2-trifluoroalkyl-1, 4-naphthoquinone compounds for the first time by taking olefin, 1, 4-naphthoquinone and sodium trifluoromethanesulfonate as reaction starting materials, taking iron salt as a catalyst and taking potassium persulfate as an oxidant. The substrate, the ferric salt catalyst and the potassium persulfate oxidant used in the method are low in price and easy to store, have the advantages of low generation cost, simplicity in operation, wide substrate range, product diversity and the like, and realize gram-scale preparation.
Drawings
FIGS. 1a, 1b and 1c are respectively a hydrogen, carbon and fluorine NMR spectrum of 2-trifluoroalkyl-1, 4-naphthoquinone 4a prepared in example 1 of the present invention;
FIGS. 2a, 2b and 2c are NMR spectra, carbon spectra and fluorine spectra of 2-trifluoroalkyl-1, 4-naphthoquinone 4b prepared in example 2 of the present invention, respectively.
Detailed Description
The present invention will be further described with reference to the accompanying drawings and examples.
Figure BDA0003626814100000041
Dispersing olefin with a structure (I), 1, 4-naphthoquinone with a structure (II), sodium trifluoromethanesulfonate with a structure (III), potassium persulfate and a catalyst in a solvent, and heating by stirring to construct a 2-trifluoroalkyl-1, 4-naphthoquinone target compound with a structure (IV); wherein, the specific structure of IV is shown as follows
Figure BDA0003626814100000051
The catalyst is ferrous sulfate heptahydrate, ferric nitrate, ferric acetylacetonate, ferric chloride or ferric oxide;
the solvent can be acetonitrile, dichloromethane, 1, 2-dichloroethane, 1, 4-dioxane, tetrahydrofuran or ethyl acetate;
the reaction temperature is 100 ℃ to 140 ℃.
Example 1
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 20 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):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＝7.7,1.1Hz,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,1H),3.13-3.00(m,2H),2.27(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.2,182.8,144.0,140.1,137.2,136.3,134.8,133.6,132.6,130.1,129.5,129.0,127.9,126.8(q,JCF＝274.1Hz),126.6,126.3,125.9,123.7,120.3,37.3(q,JCF＝27.0Hz),37.0,21.1；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.0(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C26H21F3NO2[M+H]+436.1524, found 436.1547. From the characterization data, it was confirmed that the obtained product was the objective compound 4 a.
Example 2
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-tert-butylstyrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethylsulfinate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then is placed into an oil bath kettle at the temperature of 100 ℃ for heating reaction for 20 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):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＝7.7,1.1Hz,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,1H),3.01-2.92(m,1H),1.26(s,9H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.2,182.8,149.4,144.1,140.1,137.0,134.9,133.6,132.6,130.1,129.4,127.7,126.61,126.57(q,JCF＝273.2Hz),126.3,125.8,125.2,123.8,120.4,37.4(q,JCF＝27.1Hz),37.1,34.4,27.0；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.1(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C29H27F3NO2[M+H]+ 478.1994,found 478.2005. from the characterization data, it was confirmed that the obtained product was the objective compound 4 b.
Example 3
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-acetoxystyrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 20 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):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,1H),3.17-3.08(m,1H),2.98-2.89(m,1H),2.25(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.3,182.7,169.5,149.3,144.4,139.9,137.8,135.0,133.6,132.7,130.0,129.6,129.2,126.6,126.5(q,JCF＝273.5Hz),126.4,126.2,124.0,121.3,119.0,37.7(q,JCF＝27.0Hz),37.3,21.2；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.2(t,J＝11.0Hz,3F)；HRMS(ESI-TOF):calcd.for C27H21F3NO4[M+H]+480.1423, found 480.1408. From the characterization data, it was confirmed that the obtained product was the objective compound 4 c.
Example 4
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of styrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 20 hours. After the reaction is finished, directly removing acetonitrile by a rotary evaporator,the residue was separated by silica gel column using petroleum ether and ethyl acetate as eluents to obtain the objective product as a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.11-8.06(m,2H),7.75-7.73(td,J＝7.7,1.1Hz,1H),7.66-7.63(td,J＝7.7,1.1Hz,1H),7.53(s,1H),7.20-7.11(m,6H),7.07-7.06(m,2H),7.02-7.01(d,J＝8.5Hz,2H),4.15-4.13(t,J＝7.1Hz,1H),3.17-3.08(m,1H),3.03-2.94(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.2,182.7,144.3,140.2,140.0,134.9,133.6,132.6,130.1,129.5,128.3,128.1,127.6,126.7,126.6,126.5(q,JCF＝271.8Hz),126.4,126.0,123.9,119.7,37.6,37.5(q,JCF＝27.0Hz)；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.2(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.forC25H19F3NO2[M+H]+422.1368, found 422.1378. From the characterization data, it was confirmed that the obtained product was the objective compound 4 d.
Example 5
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-fluorostyrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed in an oil bath kettle at 110 ℃ for heating reaction for 18 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.10-8.07(m,2H),7.76-7.73(td,J＝7.8,1.1Hz,1H),7.67-7.64(td,J＝7.8,1.1Hz,1H),7.58(s,1H),7.21-7.18(t,J＝7.8Hz,2H),7.15-7.11(t,J＝7.8Hz,1H),7.02-7.00(m,4H),6.87-6.84(t,J＝8.6Hz,2H),4.09-4.07(t,J＝7.1Hz,1H),3.12-3.02(m,1H),3.00-2.91(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.2,182.7,161.6(d,JCF＝243.6Hz),144.3,139.9,135.9(d,JCF＝2.6Hz),135.0,133.6,132.7,130.0,129.7(d,JCF＝7.5Hz),129.6,126.6,126.5(q,JCF＝272.8Hz),126.4,126.2,124.1,119.1,115.0(d,JCF＝21.1Hz),37.7(q,JCF＝27.2Hz),37.1；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.2(t,J＝11.0Hz,3F),-116.3(s,1F)；HRMS(ESI-TOF):calcd.for C25H18F4NO2[M+H]+440.1274, found 440.1260. From the characterization data, it was confirmed that the obtained product was the objective compound 4 e.
Example 6
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-chlorostyrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by double rows of tubes by nitrogen and then placed in an oil bath at 110 ℃ for heating reaction for 18 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.09-8.07(m,2H),7.76-7.73(td,J＝7.8,1.1Hz,1H),7.67-7.64(td,J＝7.8,1.1Hz,1H),7.61(s,1H),7.21-7.19(t,J＝7.8Hz,2H),7.16-7.13(m,3H),7.02-7.01(d,J＝7.7Hz,2H),6.99-6.98(d,J＝7.7Hz,2H),4.08-4.05(t,J＝7.0Hz,1H),3.10-3.02(m,1H),3.01-2.90(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.2,182.6,144.4,139.9,138.8,135.1,133.6,132.7,132.4,129.9,129.6,129.5,128.4,126.7(q,JCF＝273.2Hz),126.6,126.5,126.3,124.2,118.6,37.5(q,JCF＝27.0Hz),37.1；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.2(t,J＝11.0Hz,3F)；HRMS(ESI-TOF):calcd.for C25H18ClF3NO2[M+H]+456.0978, found 456.0994. From the characterization data, it was confirmed that the obtained product was the objective compound 4 f.
Example 7
0.02mmol of vinylidene sulfate heptahydrate were added sequentially to a clean 10mL Schlenk pressure-resistant reaction tubeIron, 0.3mmol of p-bromostyrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate, 0.5mmol of potassium persulfate, and 2mL of acetonitrile as a solvent are added, and the reaction tube is replaced by nitrogen through double rows and then placed in an oil bath kettle at 110 ℃ for heating reaction for 18 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.09-8.07(m,2H),7.76-7.73(td,J＝7.8,1.1Hz,1H),7.67-7.64(td,J＝7.8,1.1Hz,1H),7.61(s,1H),7.30-7.28(d,J＝8.6Hz,2H),7.21-7.19(t,J＝7.8Hz,2H),7.16-7.14(t,J＝7.8Hz,1H),7.03-7.01(d,J＝7.8Hz,2H),6.94-6.92(d,J＝7.8Hz,2H),4.06-4.04(t,J＝7.1Hz,1H),3.10-3.02(m,1H),3.01-2.91(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.1,182.6,144.4,139.8,139.4,135.1,133.6,132.7,131.3,129.9,129.6,126.64(q,JCF＝275.3Hz),126.61,126.5,126.3,124.2,120.5,118.5,37.5(q,JCF＝27.1Hz),37.2(q,JCF＝2.7Hz)；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.2(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C25H18BrF3NO2[M+H]+500.0473, found 500.0479. From the characterization data, it was confirmed that 4g of the objective compound was obtained as a product.
Example 8
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-vinyl styrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 18 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.11-8.06(m,2H),7.76-7.73(td,J＝7.8,1.1Hz,1H),7.67-7.64(td,J＝7.8,1.1Hz,1H),7.54(s,1H),7.25-7.10(m,5H),7.03-6.97(m,4H),6.62-6.57(dd,J＝17.6,10.9Hz,1H),5.65-5.62(dd,J＝17.6,0.78Hz,1H),5.19-5.18(dd,J＝10.9,0.78Hz,1H),4.14-4.12(t,J＝7.2Hz,1H),3.21-3.11(m,1H),3.05-2.89(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.3,182.7,144.3,140.5,140.0,137.5,136.9,135.0,133.6,132.6,130.0,129.5,128.5,128.2,127.6,126.6(q,JCF＝275.4Hz),126.4,126.0,124.4,124.1,113.9,37.6,37.5(q,JCF＝27.1Hz)；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.2(t,J＝10.8Hz,3F)；HRMS(ESI-TOF):calcd.for C27H21F3NO2[M+H]+448.1524, found 448.1548. From the characterization data, it was confirmed that the obtained product was the objective compound 4 h.
Example 9
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-chloromethyl styrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 18 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.09-8.07(td,J＝7.8,1.1Hz,2H),7.75-7.73(td,J＝7.7,1.1Hz,1H),7.66-7.64(td,J＝7.7,1.1Hz,1H),7.58(s,1H),7.20-7.17(m,4H),7.14-7.11(t,J＝7.6Hz,1H),7.06-7.05(d,J＝7.8Hz,2H),7.02-7.01(d,J＝7.8Hz,2H),4.51(s,2H),4.13-4.10(t,J＝7.1Hz,1H),3.14-3.06(m,1H),3.04-2.94(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.2,182.7,144.4,140.6,139.9,135.8,135.0,133.6,132.7,130.0,129.6,128.6,128.5,126.6,126.5(q,JCF＝275.7Hz),126.4,126.2,124.0,119.0,46.1,37.5(q,JCF＝27.1Hz),37.3(q,JCF＝2.8Hz)；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.1(t,J＝10.8Hz,3F)；HRMS(ESI-TOF):calcd.for C26H20ClF3NO2[M+H]+470.1135, found 470.1149. From the characterization data, it was confirmed that the obtained product was the objective compound 4 i.
Example 10
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-phenyl styrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 18 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.13-8.11(dd,J＝7.7,1.0Hz,1H),8.09-8.08(dd,J＝7.7,1.0Hz,1H),7.76-7.74(td,J＝7.7,1.1Hz,1H),7.67-7.64(td,J＝7.7,1.1Hz,1H),7.58(s,1H),7.55-7.54(m,2H),7.43-7.40(m,4H),7.33-7.30(m,1H),7.21-7.18(m,2H),7.15-7.13(m,3H),7.06-7.04(d,J＝7.7Hz,2H),4.19-4.17(t,J＝7.1Hz,1H),3.20-3.11(m,1H),3.08-2.98(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.3,182.7,144.3,140.8,140.0,139.5,139.3,135.0,133.6,132.7,130.1,129.5,128.8,128.5,127.3,127.1,127.0,126.7(q,JCF＝273.6Hz),126.6,126.4,126.1,124.0,119.5,37.5(q,JCF＝27.0Hz),37.3；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.1(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C31H23F3NO2[M+H]+498.1681, found 498.1707. From the characterization data, it was confirmed that the obtained product was the objective compound 4 j.
Example 11
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of 2-naphthylethylene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, and then the mixture is addedAdding 2mL of acetonitrile as a solvent, replacing the reaction tube with nitrogen through double rows, and then placing the reaction tube in an oil bath kettle at 100 ℃ for heating reaction for 18 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.13-8.11(dd,J＝7.7,1.1Hz,1H),8.09-8.07(dd,J＝7.7,1.1Hz,1H),7.76-7.73(m,2H),7.71-7.69(m,1H),7.67-7.64(m,2H),7.58(s,1H),7.48(s,1H),7.43-7.39(m,2H),7.20-7.18(dd,J＝8.6,1.9Hz,1H),7.15-7.09(m,3H),7.05-7.03(m,2H),4.33-4.30(t,J＝7.1Hz,1H),3.26-3.17(m,1H),3.13-3.04(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.3,182.7,144.3,140.0,137.7,135.0,133.6,133.3,132.7,132.3,130.1,129.5,128.0,127.9,127.6,127.5,126.8,126.77,126.72(q,JCF＝274.2Hz),126.5,126.4,126.05,126.02,125.8,124.0,119.5,37.7(q,JCF＝2.9Hz),37.4(q,JCF＝27.1Hz)；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.1(t,J＝10.8Hz,3F)；HRMS(ESI-TOF):calcd.for C29H21F3NO2[M+H]+472.1524, found 472.1551. From the characterization data, it was confirmed that the obtained product was the objective compound 4 k.
Example 12
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of 3-chlorostyrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed in an oil bath kettle at 100 ℃ for heating reaction for 18 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.10-8.07(m,2H),7.77-7.74(td,J＝7.7,1.1Hz,1H),7.67-7.64(td,J＝7.7,1.1Hz,1H),7.61(s,1H),7.21-7.14(m,3H),7.13-7.09(m,2H),7.02-7.10(d,J＝7.5Hz,2H),6.97-6.94(m,2H),4.08-4.05(t,J＝7.1Hz,1H),3.16-3.07(m,1H),2.94-2.85(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.1,182.6,144.7,142.4,139.8,135.1,134.0,133.6,132.7,129.9,129.5,129.4,128.4,126.8,126.7,126.6(q,JCF＝271.6Hz),126.5,126.3,124.4,118.2,37.6(q,JCF＝27.1Hz),37.5；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.2(t,J＝11.0Hz,3F)；HRMS(ESI-TOF):calcd.for C25H18ClF3NO2[M+H]+456.0978, found 456.0994. From the characterization data, it was confirmed that the obtained product was 4l of the objective compound.
Example 13
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of 3-bromostyrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 18 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.10-8.07(m,2H),7.77-7.74(td,J＝7.7,1.1Hz,1H),7.67-7.64(td,J＝7.7,1.1Hz,1H),7.61(s,1H),7.28-7.26(dt,J＝7.0,2.0Hz,1H),7.21-7.16(m,3H),7.06-7.01(m,5H),4.07-4.04(t,J＝7.1Hz,1H),3.17-3.07(m,1H),2.92-2.83(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.2,182.6,144.7,142.7,139.8,135.1,133.6,132.7,131.3,129.9,129.78,129.76,129.5,126.8,126.7,126.6(q,JCF＝273.4Hz),126.5,124.5,122.3,118.1,37.6(q,JCF＝27.0Hz),37.5(q,JCF＝2.8Hz)；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.2(t,J＝11.0Hz,3F)；HRMS(ESI-TOF):calcd.for C25H18BrF3NO2[M+H]+500.0473, found 500.0479. From the characterization data, it was confirmed that the obtained product was of interestTarget compound 4 m.
Example 14
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of 2-chlorostyrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed in an oil bath kettle at 100 ℃ for heating reaction for 18 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.17-8.15(dd,J＝7.7,1.1Hz,1H),8.10-8.09(dd,J＝7.7,1.1Hz,1H),7.79-7.76(td,J＝7.7,1.1Hz,1H),7.69-7.66(td,J＝7.8,1.1Hz,1H),7.63(s,1H),7.46-7.45(d,J＝7.7Hz,1H),7.18-7.16(m,1H),7.13-7.12(m,2H),7.08-7.05(t,J＝7.1Hz,1H),7.00-6.97(t,J＝7.1Hz,2H),6.79-6.78(d,J＝7.7Hz,2H),4.32-4.30(t,J＝7.1Hz,1H),3.36-3.26(m,1H),2.83-2.75(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.8,182.5,145.2,139.3,136.6,135.0,134.7,133.7,132.7,130.7,130.1,129.4,129.1,128.4(q,JCF＝273.2Hz),128.2,126.7,126.5,125.8,123.5,116.9,36.8(q,JCF＝2.9Hz),35.2(q,JCF＝27.1Hz)；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.3(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C25H18ClF3NO2[M+H]+456.0978, found 456.0994. From the characterization data, it was confirmed that the obtained product was the objective compound 4 n.
Example 15
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of 4-trifluoromethylstyrene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 18 hours. After the reaction is finished, directly removing the reaction product by a rotary evaporatorAcetonitrile is removed, and the obtained residue is separated by a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.10-8.08(dd,J＝7.7,1.2Hz,2H),7.77-7.74(td,J＝7.7,1.1Hz,1H),7.68-7.65(m,2H),7.43-7.42(d,J＝7.7Hz,2H),7.19-7.13(m,5H),7.03-7.02(d,J＝7.8Hz,2H),4.16-4.13(t,J＝7.1Hz,1H),3.13-2.94(m,2H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.1,182.5,144.7,144.5,139.7,135.1,133.5,132.8,129.9,129.6,128.8(q,JCF＝32.0Hz),128.4,126.6,126.52,126.46(q,JCF＝276.3Hz),125.2,125.1,124.3,124.2(q,JCF＝274.1Hz),117.9,37.5,37.4(q,JCF＝27.3Hz)；19F NMR(564MHz,CDCl3):δ[ppm]-62.3(s,3F), -64.2(t, J ═ 10.8Hz, 3F). From the characterization data, it was confirmed that the obtained product was the target compound 4 zb.
Example 16
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of 3-phenylpropylene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.11-8.10(dd,J＝7.7,1.1Hz,1H),8.07-8.05(dd,J＝7.7,1.1Hz,1H),7.78-7.75(td,J＝7.7,1.1Hz,1H),7.67-7.64(td,J＝7.7,1.1Hz,1H),7.41-7.39(t,J＝7.7Hz,2H),7.27-7.25(m,2H),7.13-7.11(m,5H),6.58-6.57(m,2H),3.23-3.08(m,2H),2.92-2.87(m,1H),2.74-2.65(m,1H),2.22-2.12(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.4,182.5,144.9,141.2,139.2,134.9,133.8,132.6,129.99,129.96,129.0,128.3,127.2(q,JCF＝274.3Hz),126.4,126.3,126.1,123.2,120.3,37.2,34.9(q,JCF＝27.0Hz),34.1；19F NMR(564MHz,CDCl3):δ[ppm]＝-63.7(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C26H21F3NO2[M+H]+436.1524, found 436.1547. From the characterization data, it was confirmed that the obtained product was 4o, the objective compound.
Example 17
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of 5-oxo-1-hexene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double tubes and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.07-8.04(td,J＝7.7,1.1Hz,2H),7.75-7.72(td,J＝7.7,1.1Hz,1H),7.66-7.64(td,J＝7.7,1.1Hz,1H),7.47(s,1H),7.36-7.33(t,J＝7.8Hz,2H),7.23-7.20(t,J＝7.8Hz,1H),7.12-7.11(d,J＝8.0Hz,2H),2.71-2.62(m,2H),2.39-2.29(m,1H),2.25-2.19(m,1H),2.13-2.06(m,1H),2.04(s,3H),1.89-1.83(m,1H),1.80-1.75(m,1H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝208.1,184.1,182.5,144.7,141.0,134.8,133.5,132.7,130.2,129.7,126.8(q,JCF＝274.8Hz),126.4,126.3,126.0,124.1,121.4,41.9,35.9(q,JCF＝27.0Hz),32.0,29.9,26.6；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.0(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C23H21F3NO3[M+H]+416.1474, found 416.1484. From the characterization data, it was confirmed that the obtained product was the target compound 4 p.
Example 18
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of 4-p-tert-butylphenoxy-1-butene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone and 0.4mmol of trifluoromethyl-methyleneimine are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tubeSodium sulfonate, 0.5mmol potassium persulfate, and then 2mL acetonitrile are added as solvent, the reaction tube is replaced by nitrogen through double-row tube, and then the reaction tube is placed in an oil bath pan with 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.07-8.05(dd,J＝7.7,1.1Hz,1H),8.04-8.03(dd,J＝7.7,1.1Hz,1H),7.75-7.72(td,J＝7.7,1.1Hz,1H),7.66-7.63(td,J＝7.8,1.1Hz,1H),7.33-7.30(m,3H),7.24-7.23(m,1H),7.19-7.16(m,2H),7.02-7.00(m,2H),6.67-6.64(m,2H),3.69-3.66(m,1H),3.63-3.59(m,1H),3.09-3.04(m,1H),2.76-2.69(m,1H),2.63-2.58(m,1H),2.35-2.29(m,1H),2.17-2.13(m,1H),1.28(s,9H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.3,182.2,156.2,144.9,143.6,141.2,134.7,133.6,132.7,130.4,129.6,127.2(q,JCF＝272.6Hz),126.4,126.3,125.7,123.7,121.7,113.9,66.1,36.3(q,JCF＝27.0Hz),34.2,32.0,31.6,30.2；19F NMR(564MHz,CDCl3):δ[ppm]＝-63.7(t,J＝11.0Hz,3F)；HRMS(ESI-TOF):calcd.for C31H31F3NO3[M+H]+522.2256, found 522.2239. From the characterization data, it was confirmed that the obtained product was the objective compound 4 q.
Example 19
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of 1-octene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.08-8.05(td,J＝7.7,1.1Hz,2H),7.74-7.71(td,J＝7.7,1.1Hz,1H),7.65-7.63(td,J＝7.7,1.1Hz,1H),7.36-7.33(m,3H),7.22-7.20(t,J＝7.8Hz,1H),7.13-7.12(d,J＝7.8Hz,2H),2.67-2.58(m,2H),2.38-2.30(m,1H),1.88-1.82(m,1H),1.51-1.45(m,1H),1.24-1.03(m,8H),0.85-0.83(t,J＝7.2Hz,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.3,182.8,144.4,141.0,134.8,133.7,132.5,130.1,129.6,127.1(q,JCF＝275.7Hz),126.32,126.29,126.0,124.2,122.1,35.6(q,JCF＝27.0Hz),32.8,32.5,31.8,29.3,28.0,22.7,14.2；19F NMR(564MHz,CDCl3):δ[ppm]＝-63.9(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C25H27F3NO2[M+H]+430.1994, found 430.2012. From the characterization data, it was confirmed that the obtained product was the objective compound 4 r.
Example 20
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2-p-ethylphenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double tubes and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.08-8.06(dd,J＝7.7,1.1Hz,1H),8.05-8.04(dd,J＝7.7,1.2Hz,1H),7.74-7.71(td,J＝7.7,1.1Hz,1H),7.64-7.61(td,J＝7.7,1.1Hz,1H),7.50(s,1H),7.03-7.02(d,J＝8.2Hz,2H),7.00-6.95(m,6H),4.13-4.11(t,J＝7.1Hz,1H),3.08-2.99(m,2H),2.60-2.56(q,J＝7.6Hz,2H),2.26(s,3H),1.20-1.18(t,J＝7.6Hz,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.2,182.9,144.4,142.4,137.6,137.4,136.1,134.9,133.7,132.5,130.1,129.5,128.0,126.7(q,JCF＝273.5Hz),126.5,126.3,124.2,119.4,37.3(q,JCF＝27.0Hz),36.9,28.5,21.1,15.7；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.0(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C28H25F3NO2[M+H]+464.1837, found 464.1829. From the characterization data, it was confirmed that the obtained product was the objective compound 4 s.
Example 21
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2-p-methylphenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double tubes and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.08-8.07(dd,J＝7.6,1.1Hz,1H),8.06-8.04(dd,J＝7.7,1.1Hz,1H),7.73-7.71(td,J＝7.7,1.1Hz,1H),7.64-7.61(td,J＝7.7,1.1Hz,1H),7.49(s,1H),7.01-6.96(m,6H),6.94-6.93(d,J＝8.2Hz,2H),4.15-4.13(t,J＝7.1Hz,1H),3.12-2.97(m,2H),2.29(s,3H),2.27(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.1,182.9,144.3,137.45,137.42,136.1,136.0,134.9,133.7,132.5,130.1,130.0,128.9,127.9,126.8(q,JCF＝271.2Hz),126.5,126.3,124.1,119.4,37.2(q,JCF＝27.1Hz),36.8,21.1,21.0；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.0(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C27H23F3NO2[M+H]+450.1681, found 450.1702. From the characterization data, it was confirmed that the obtained product was the target compound 4 t.
Example 22
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2-p-fluoroanilino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double tubes and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. Reaction(s) ofAfter the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.09-8.08(d,J＝7.7Hz,1H),8.07-8.06(d,J＝7.7Hz,1H),7.75-7.73(t,J＝7.7Hz,1H),7.66-7.64(t,J＝7.7Hz,1H),7.42(s,1H),7.00-6.96(m,4H),6.93-6.91(d,J＝8.1Hz,2H),6.86-6.83(t,J＝8.1Hz,2H),4.07-4.05(t,J＝7.1Hz,1H),3.19-3.09(m,1H),2.92-2.83(m,1H),2.27(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.3,182.7,160.8(d,JCF＝245.9Hz),144.5,137.0,136.4,136.1(d,JCF＝3.0Hz),135.0,133.6,132.7,130.0,129.1,127.8,126.8(q,JCF＝274.5Hz),126.7,126.4,126.0(d,JCF＝8.5Hz),119.5,116.2(d,JCF＝22.6Hz),37.7(q,JCF＝27.0Hz),37.0(q,JCF＝2.9Hz),21.1；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.3(t,J＝10.9Hz,3F),-115.6(s,1F)；HRMS(ESI-TOF):calcd.for C26H20F4NO2[M+H]+454.1430, found 454.1413. From the characterization data, it was confirmed that the obtained product was the objective compound 4 u.
Example 23
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2-m-methylphenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double tubes and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluents to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.10-8.09(dd,J＝7.7,1.1Hz,1H),8.07-8.05(dd,J＝7.7,1.1Hz,1H),7.75-7.72(td,J＝7.6,1.1Hz,1H),7.65-7.62(td,J＝7.6,1.1Hz,1H),7.52(s,1H),7.15-7.12(t,J＝8.1Hz,1H),7.01-6.96(m,4H),6.92-6.89(m,2H),6.74(s,1H),4.11-4.09(t,J＝7.1Hz,1H),3.14-3.04(m,1H),3.01-2.92(m,1H),2.27(s,3H),2.05(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.1,182.8,144.2,139.9,139.7,137.2,136.1,134.9,133.7,132.5,130.1,129.3,129.0,128.0,126.7(q,JCF＝273.7Hz),126.65,126.60,126.3,124.4,120.8,119.5,37.6(q,JCF＝27.0Hz),37.2,21.0,21.0；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.2(t,J＝11.0Hz,3F)；HRMS(ESI-TOF):calcd.for C27H23F3NO2[M+H]+450.1681, found 450.1702. From the characterization data, it was confirmed that the obtained product was 4v, the objective compound.
Example 24
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2-m-chlorophenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethylsulfinate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double lines and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluents to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.11-8.09(dd,J＝7.7,1.1Hz,1H),8.06-8.05(dd,J＝7.6,1.1Hz,1H),7.76-7.73(td,J＝7.7,1.1Hz,1H),7.67-7.64(td,J＝7.6,1.1Hz,1H),7.33(s,1H),7.13-7.10(t,J＝8.1Hz,1H),7.07-7.05(d,J＝8.1Hz,1H),7.03-6.94(m,5H),6.91-6.89(m,1H),4.12-4.10(t,J＝7.1Hz,1H),3.15-2.97(m,2H),2.27(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.3,182.5,143.7,141.7,136.6,136.5,135.3,134.9,133.4,132.9,130.4,130.1,129.3,127.9,126.7,126.6(q,JCF＝274.6Hz),126.4,125.5,123.2,122.4,121.2,37.7,37.4(q,JCF＝27.0Hz),21.1；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.3(t,J＝11.0Hz,3F)；HRMS(ESI-TOF):calcd.for C26H20ClF3NO2[M+H]+470.1135, found 470.1149. From the characterization data, it was confirmed that the obtained product was the objective compound 4 w.
Example 25
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2- (2-naphthylamino) -1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double tubes and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.14-8.13(dd,J＝7.5,1.1Hz,1H),8.10-8.09(dd,J＝7.6,1.1Hz,1H),7.78-7.68(m,4H),7.68-7.65(m,1H),7.41-7.36(m,2H),7.33-7.32(d,J＝7.9Hz,1H),7.22-7.20(dd,J＝7.7,0.8Hz,1H),6.89-6.85(m,4H),4.15-4.13(dd,J＝8.3,6.1Hz,1H),3.25-3.15(m,1H),2.86-2.77(m,1H),2.23(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝184.3,182.8,144.3,137.4,136.8,136.3,134.9,133.7,133.6,132.7,131.2,130.1,129.5,129.0,127.9,127.6,127.4,127.0(q,JCF＝271.8Hz),126.7,126.5,126.4,125.7,122.6,120.8,120.4,37.8(q,JCF＝27.0Hz),37.7(q,JCF＝2.8Hz),21.0；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.2(t,J＝10.8Hz,3F)；HRMS(ESI-TOF):calcd.for C30H23F3NO2[M+H]+486.1681, found 486.1680. From the characterization data, it was confirmed that the obtained product was 4x as the target compound.
Example 26
Sequentially adding 0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2- (N-methylphenylamino) -1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate into a clean 10mL Schlenk pressure-resistant reaction tube, then adding 2mL of acetonitrile as a solvent, replacing the reaction tube with nitrogen through double rows, and then placing the reaction tube into an oil bath kettle at 100 ℃ for heating reaction 2For 4 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.12-8.10(dd,J＝7.7,1.1Hz,1H),7.95-7.94(dd,J＝7.7,1.1Hz,1H),7.75-7.72(td,J＝7.7,1.1Hz,1H),7.70-7.67(td,J＝7.7,1.1Hz,1H),7.22-7.19(m,4H),7.05-7.04(d,J＝8.2Hz,2H),6.88-6.85(tt,J＝7.8,1.1Hz,1H),6.69-6.67(dd,J＝7.8,1.1Hz,2H),4.78-4.76(dd,J＝8.3,6.1Hz,1H),3.51-3.42(m,1H),3.13(s,3H),2.97-2.88(m,1H),2.28(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝186.1,182.0,150.5,148.3,146.4,137.1,136.1,134.1,134.0,132.6,131.8,129.4,129.3,128.9,126.8(q,JCF＝273.1Hz),126.7,126.6,119.7,114.4,39.8,38.5,37.2(q,JCF＝27.0Hz),21.1；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.3(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C27H23F3NO2[M+H]+450.1681, found 450.1702. From the characterization data, it was confirmed that the obtained product was the objective compound 4 y.
Example 27
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2-phenylethylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a light red solid as a target product. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.01-8.00(d,J＝7.6Hz,1H),7.97-7.96(d,J＝7.7Hz,1H),7.67-7.65(td,J＝7.7,1.1Hz,1H),7.58-7.55(td,J＝7.7,1.1Hz,1H),7.32-7.30(t,J＝7.7Hz,2H),7.25-7.23(m,1H),7.17-7.16(d,J＝8.2Hz,2H),7.14-713(d,J＝8.2Hz,2H),7.09-7.08(d,J＝8.2Hz,2H),5.81(s,1H),4.61-4.59(dd,J＝8.8,4.6Hz,1H),3.82-3.72(m,2H),3.36-3.27(m,1H),2.95-2.87(m,3H),2.30(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝183.1,182.8,146.6,138.8,137.5,136.3,134.7,133.6,132.1,130.2,129.4,128.9,128.7,127.3,127.2(q,JCF＝272.5Hz),127.1,126.3,126.2,115.9,47.2,36.8,36.7(q,JCF＝26.8Hz),36.0,21.1；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.0(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.forC28H25F3NO2[M+H]+464.1837, found 464.1829. From the characterization data, it was confirmed that the obtained product was the target compound 4 z.
Example 28
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2-octylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethylsulfinate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by double-row nitrogen and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a light red solid as a target product. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.02-8.00(d,J＝8.1Hz,1H),8.00-7.98(d,J＝8.0Hz,1H),7.68-7.65(td,J＝7.7,1.1Hz,1H),7.58-7.55(td,J＝7.7,1.1Hz,1H),7.25-7.24(d,J＝7.7Hz,2H),7.11-7.10(d,J＝7.8Hz,2H),5.89(s,1H),4.65-4.63(dd,J＝8.8,4.6Hz,1H),3.52-3.36(m,3H),3.06-2.97(m,1H),2.29(s,3H),1.65-1.60(m,3H),1.32-1.24(m,9H),0.88-0.86(t,J＝7.6Hz,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝183.1,182.9,146.6,139.3,136.2,134.7,133.8,132.1,129.9,129.3,127.3,127.2(q,JCF＝271.8Hz),126.3,126.2,115.1,46.5,36.9(q,JCF＝26.7Hz),36.0,31.8,30.7,29.2,29.1,26.7,22.7,21.0,14.2；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.0(t,J＝11.0Hz,3F)；HRMS(ESI-TOF):calcd.for C28H33F3NO2[M+H]+472.2463, found 472.2488. From the characterization data, it was confirmed that the obtained product was 4za as the objective compound.
Example 29
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through a double-row tube and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a light yellow solid as a target product. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.05-8.02(m,2H),7.72-7.69(m,2H),7.21-7.19(d,J＝8.1Hz,2H),7.13-7.11(d,J＝8.1Hz,2H),6.85(s,1H),4.63-4.60(t,J＝7.1Hz,1H),2.98-2.89(m,1H),2.80-2.71(m,1H),2.29(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝185.1,184.0,151.0,137.6,136.0,134.6,134.0,132.2,131.8,129.8,127.8,127.0,126.2,38.4,37.6,(q,JCF＝27.4Hz),21.1；19F NMR(564MHz,CDCl3):δ[ppm]＝-63.8(t,J＝11.0Hz,3F)；HRMS(ESI-TOF):calcd.for C20H16F3O2[M+H]+345.1102, found 345.1116. From the characterization data, it was confirmed that the obtained product was the objective compound 4 zc.
Example 30
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2-methyl-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a light yellow solid as a target product. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.05-8.04(m,1H),7.99-7.96(m,1H),7.68-7.64(m,2H),7.24-7.23(d,J＝7.6Hz,2H),7.11-7.10(d,J＝7.6Hz,2H),4.59-4.57(dd,J＝10.2,4.5Hz,1H),3.53-3.43(m,1H),2.99-2.90(m,1H),2.36(s,3H),2.29(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝185.2,184.5,145.8,144.9,137.0,136.6,133.7,133.6,132.3,131.8,129.5,127.6,127.0(q,JCF＝275.6Hz),126.5,126.4,38.8,36.4(q,JCF＝27.3Hz),21.1,13.0；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.4(t,J＝10.8Hz,3F)；HRMS(ESI-TOF):calcd.for C21H18F3O2[M+H]+359.1259, found 359.1288. From the characterization data, it was confirmed that the obtained product was the objective compound 4 zd.
Example 31
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of p-methylstyrene, 0.2mmol of 2-hydroxy-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate and 0.5mmol of potassium persulfate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through double rows and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain an orange solid serving as a target product. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝8.10-8.08(d,J＝7.7Hz,1H),8.04-8.03(d,J＝7.6Hz,1H),7.75-7.73(t,J＝7.6Hz,1H),7.67-7.64(t,J＝7.6Hz,1H),7.36-7.35(d,J＝8.0Hz,2H),7.10-7.09(d,J＝7.9Hz,2H),4.84-4.81(dd,J＝9.7,5.1Hz,1H),3.49-3.39(m,1H),2.92-2.83(m,1H),2.28(s,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝183.9,181.6,152.9,137.6,136.9,135.3,133.2,132.8,129.4,129.1,128.0,127.2,126.8(q,JCF＝274.3Hz),126.3,123.4,35.7(q,JCF＝27.4Hz),34.4,21.1；19F NMR(564MHz,CDCl3):δ[ppm]＝-64.8(t,J＝10.9Hz,3F)；HRMS(ESI-TOF):calcd.for C20H16F3O3[M+H]+ 361.1052, found 361.1068. From the characterization data, it was confirmed that the product obtained was the target compound 4 ze.
Example 32
0.02mmol of ferrous sulfate heptahydrate, 0.3mmol of 4-bromo-1-butene, 0.2mmol of 2-phenylamino-1, 4-naphthoquinone, 0.4mmol of sodium trifluoromethanesulfonate, 0.5mmol of potassium persulfate and 0.2mmol of potassium carbonate are sequentially added into a clean 10mL Schlenk pressure-resistant reaction tube, 2mL of acetonitrile is added as a solvent, the reaction tube is replaced by nitrogen through a double-row tube and then placed into an oil bath kettle at 100 ℃ for heating reaction for 24 hours. After the reaction is finished, acetonitrile is directly removed through a rotary evaporator, and the obtained residue is separated through a silica gel column by using petroleum ether and ethyl acetate as eluent to obtain a target product which is a red solid. The characterization data are:1H NMR(600MHz,CDCl3):δ[ppm]＝7.89-7.88(dd,J＝7.7,1.1Hz,1H),7.78-7.77(dd,J＝7.7,1.1Hz,1H),7.63-7.60(td,J＝7.8,1.1Hz,1H),7.42-7.39(td,J＝7.7,1.2Hz,1H),7.34-7.31(m,2H),7.08-7.05(tt,J＝7.8,1.1Hz,1H),6.69-6.68(m,2H),4.55-4.53(m,1H),4.32-4.27(m,1H),3.53-3.51(m,1H),2.90-2.81(m,1H),2.23-2.16(m,3H)；13C{1H}NMR(150MHz,CDCl3):δ[ppm]＝180.0,128.3,154.1,151.5,134.6,132.9,131.2,129.7,129.0,128.5,123.4,123.0,116.6,113.8,63.2,36.5(q,JCF＝27.1Hz),24.9,23.8；19F NMR(564MHz,CDCl3):δ[ppm]＝-62.9(t,J＝11.0Hz,3F)；HRMS(ESI-TOF):calcd.for C21H17F3NO2[M+H]+372.1211, found 372.1229. From the characterization data, it was confirmed that the obtained product was the target compound 4 zf.
In one embodiment, the 2-trifluoroalkyl-1, 4-naphthoquinone compound and the synthesis method thereof disclosed by the invention are characterized in that under the catalysis of iron salt and the oxidation effect of potassium persulfate, sodium trifluoromethanesulfonate is triggered to generate a trifluoromethyl radical through a radical process, then the trifluoromethyl radical is oxidized by potassium persulfate after the trifluoromethyl radical is subjected to radical relay addition with corresponding olefin and 1, 4-naphthoquinone, and then the 2-trifluoroalkyl-1, 4-naphthoquinone compound is prepared through deprotonation.
The foregoing is a description of the preferred embodiments of the present invention to enable those skilled in the art to make or use the invention, and certain modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the scope or spirit of the invention. Accordingly, the scope of the invention is not limited by the specific embodiments described above.

Claims (4)

1. A2-trifluoroalkyl-1, 4-naphthoquinone compound and a synthetic method thereof are disclosed, which comprises the following steps:
Figure FDA0003626814090000011
dispersing olefin with a structure (I), 1, 4-naphthoquinone with a structure (II), sodium trifluoromethanesulfonate with a structure (III), potassium persulfate and a catalyst in a solvent, and heating by stirring to construct a 2-trifluoroalkyl-1, 4-naphthoquinone target compound with a structure (IV); wherein, the specific structure of IV is shown below
Figure FDA0003626814090000012
2. The 2-trifluoroalkyl-1, 4-naphthoquinone compound and the synthesis method thereof according to claim 1, wherein the synthesis method comprises the following steps: the catalyst is ferrous sulfate heptahydrate, ferric nitrate, ferric acetylacetonate, ferric chloride or ferric oxide.
3. The 2-trifluoroalkyl-1, 4-naphthoquinone compound and the synthesis method thereof according to claim 1, wherein: the solvent can be acetonitrile, dichloromethane, 1, 2-dichloroethane, 1, 4-dioxane, tetrahydrofuran or ethyl acetate.
4. The 2-trifluoroalkyl-1, 4-naphthoquinone compound and the synthesis method thereof according to claim 1, wherein: the reaction temperature is 100 ℃ to 140 ℃.
CN202210478856.4A 2022-05-05 2022-05-05 2-trifluoroalkyl-1, 4-naphthoquinone compound and synthetic method thereof Pending CN114702399A (en)

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