Synthesis and application of bifunctional fluorescent probe for simultaneously distinguishing hydroxyl radicals and hydrogen peroxide
A fluorescent probe, hydrogen peroxide technology, applied in the field of analytical chemistry, can solve the problems of simultaneous detection of dual-functional fluorescent probes that have not been reported
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Embodiment 1
[0027] Example 1. Synthesis of methyl 3-(8-methoxy-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinoxalin-5(1H)-yl)propionate
[0028] a. Add 30 g (175.31 mmol) 3-fluoro-4-nitroanisole and 37.5 g (227.9 mmol) L-proline methyl ester hydrochloride to 200 mL of anhydrous acetonitrile, then add 73 mL ( 525.9 mmol) triethylamine heating and reflux reaction for 6 hours, filtered to remove triethylamine hydrochloride, spin-dried solution,
[0029] b. Dissolve the spin-dried solution with 300 mL of methanol, slowly add 46.76 g (874.13 mmol) of ammonium chloride and 57.15 g (874.13 mmol) of zinc powder, stir overnight at room temperature, then filter to remove the zinc powder, spin to dry the solvent, The solid was added to water, filtered and dried to obtain a green solid,
[0030]c. Dissolve the green solid in 400 mL of anhydrous tetrahydrofuran, add 36.4 g (962.17 mmol) of sodium borohydride and 122 mL (962.17 mmol) of boron trifluoride ether, and react at 90°C for 12 hours. After the reactio...
Embodiment 2
[0032] Example 2. Synthesis of 3-(7-formyl-8-hydroxyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinoxalin-5(1H)-yl)propionic acid methyl ester
[0033] . Under nitrogen protection, add 10 mL (61.99 mmol) of phosphorus oxychloride (POCl 3 ), stirred at 20-50°C for 30-60 minutes to obtain a yellow solution, and 10 g (34.44 mmol) of 3-(8-methoxy-2,3,3a,4-tetrahydropyrrolo[1, 2-a] quinoxaline-5(1H)-yl)propionic acid methyl ester was dissolved in 40mL N,N-dimethylformamide (DMF), and was added dropwise to the yellow mixed solution, and the mixture was continuously heated under nitrogen Stir and react at 60°C for 12 hours under protection; after the reaction is complete, pour the reaction solution into an appropriate amount of ice water, adjust the pH to 5~6 with 20% NaOH solution, then extract with ethyl acetate, spin the organic layer to obtain a yellow liquid product.
[0034] . Add 621.8 mg (23.05 mmol) of aluminum and 5.85 g (23.05 mmol) of iodine into 15 mL of anhydrous aceto...
Embodiment 3
[0035] Example 3. Synthesis of methyl 3-(7-(2,2-dicyanovinyl)-8-((4-(4,4,5,5-tetramethyl-1,3,2-di Oxaborolan-2-yl)benzyl)oxy)-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinoxalin-5(1H)-yl)propionate
[0036] . Methyl 3-(7-formyl-8-hydroxy-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinoxalin-5(1H)-yl)propionate 200 mg (658.15 μmol) and 4-bromophenylboronic acid pinacol ester 390.30 mg (1.30mmol) were added to 8 mL of acetonitrile, then potassium carbonate 136.16 mg (985.70 μmol) was added, and refluxed overnight. After the reaction was completed, column chromatography purified to obtain a yellow solid 120.0 mg, yield 35.09%.
[0037] . Step Add 120 mg (230.58 μmol) of medium yellow solid and 18.3 mg (276.69 μmol) of malononitrile into 6 mL of ethanol, then add a drop of piperidine, react overnight at room temperature, and filter to obtain the fluorescent molecular probe 3- (7-(2,2-Dicyanovinyl)-8-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) Benzyl)oxy)-2,3,3a,4-tetrahydropyrrolo[1,...
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