Naphthoquinone-based fluorescent bisulfite probe and preparation and application thereof
A bisulfite and fluorescent probe technology, applied in the preparation of carboxylic acid nitriles, organic compounds, fluorescence/phosphorescence, etc., can solve the problems of poor selectivity and achieve rapid detection, high sensitivity, and good selectivity
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Embodiment 1
[0029] Compound (Z)-2-cyano-2-(2-oxonaphthylene-1(2H)-ylidene) ethyl acetate (1-a) and (E)-2-cyano-2-( Synthesis of 2-oxonaphthylidene-1(2H)-ylidene)(1-b)
[0030] Weigh 1.00 g (5.49 mmol) of acenaphthenequinone, dissolve it in 20 mL of toluene, add 0.62 g (5.56 mmol) of ethyl cyanoacetate, 0.1 g (1.30 mmol) of ammonium acetate, and 0.3 g (5.00 mmol) of acetic acid. React at 100°C for 6 hours. After the reaction is over, cool to room temperature and remove toluene with a rotary evaporator. Add aqueous sodium bicarbonate solution for dilution, extract with dichloromethane and water, and dry the organic phase with magnesium sulfate. Combine Concentrate to obtain a yellow-gray solid, which is recrystallized with chloroform and n-hexane to obtain a mixture of compounds 1-a and 1-b, wherein 1-b is more soluble in n-hexane, and 1-a and 1-b in the mixture are identified by NMR. The content of b is about 1:1.
[0031] 1H NMR (CDCl3, 400MHz, ppm): 8.74(d, J=7.40Hz, 1H), 8.44(dd, J=7....
Embodiment 2
[0037] Compound (Z)-2-cyano-2-(2-oxonaphthylene-1(2H)-ylidene) ethyl acetate (1-a) and (E)-2-cyano-2-( Synthesis of 2-oxonaphthylidene-1(2H)-ylidene)(1-b)
[0038] Weigh 1.00 g (5.49 mmol) of acenaphthenequinone, dissolve it in 20 mL of toluene, add 1.22 g (10.98 mmol) of ethyl cyanoacetate, 0.17 g (2.2 mmol) of ammonium acetate, and 0.16 g (2.74 mmol) of acetic acid. React at reflux temperature of 110°C for 8 hours. After the reaction, cool to room temperature, remove toluene with a rotary evaporator, add aqueous sodium bicarbonate solution for dilution, extract with dichloromethane and water, and dry the organic phase with magnesium sulfate , were combined and concentrated to obtain a yellow-gray solid, which was recrystallized with chloroform and n-hexane to obtain a mixture of compounds 1-a and 1-b, wherein 1-b was more easily soluble in n-hexane, and 1-a and 1-b in the mixture were identified by NMR. The content of 1-b is about 1:1.
[0039] Synthesis of probe (I):
[...
Embodiment 3
[0042] Compound (Z)-2-cyano-2-(2-oxonaphthylene-1(2H)-ylidene) ethyl acetate (1-a) and (E)-2-cyano-2-( Synthesis of 2-oxonaphthylidene-1(2H)-ylidene)(1-b)
[0043] Weigh 1.00 g (5.49 mmol) of acenaphthenequinone, dissolve it in 20 mL of toluene, add 1.86 g (16.47 mmol) of ethyl cyanoacetate, 0.21 g (2.74 mmol) of ammonium acetate, and 0.49 g (8.24 mmol) of acetic acid. React at 120°C for 10 hours. After the reaction, cool to room temperature, remove toluene with a rotary evaporator, add aqueous sodium bicarbonate solution for dilution, extract with dichloromethane and water, dry the organic phase with magnesium sulfate, combine and concentrate A yellow-gray solid was obtained, which was recrystallized with chloroform and n-hexane to obtain a mixture of compounds 1-a and 1-b, wherein 1-b was more easily soluble in n-hexane, and 1-a and 1-b in the mixture were identified by NMR The content is about 1:1.
[0044] Synthesis of probe (I):
[0045] Weigh the mixture (Z)-2-cyano-2...
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