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4-trifluoromethyl-6-bromo-2-substituted acetonitrile-1,8-naphthalimide compounds as well as preparation method and application thereof

A technology of naphthalimide and trifluoromethyl, which is applied in the field of organic photoelectric or fluorescent probes, can solve the problems that there are not many naphthalimide derivatives, and there are no reports on naphthalimide derivatives. Ultra-high sensitivity and selectivity, low production cost, and simple synthetic route

Active Publication Date: 2018-12-21
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In summary, there are not many reports on the 2-position CH group-containing naphthalimide derivatives, especially the 2-aryl acetonitrile-based naphthalimide derivatives have not been reported so far.

Method used

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  • 4-trifluoromethyl-6-bromo-2-substituted acetonitrile-1,8-naphthalimide compounds as well as preparation method and application thereof
  • 4-trifluoromethyl-6-bromo-2-substituted acetonitrile-1,8-naphthalimide compounds as well as preparation method and application thereof
  • 4-trifluoromethyl-6-bromo-2-substituted acetonitrile-1,8-naphthalimide compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] A 4-trifluoromethyl-1,8-naphthalimide compound, its structural formula is as follows:

[0045]

[0046] where R 1 is n-butyl;

[0047] The reaction equation of its synthetic process is as follows:

[0048]

[0049] The concrete steps of its preparation method are as follows:

[0050] In a 50ml one-mouth bottle, first add 2.0g (6.04mmol) N-n-butyl-4-bromo-1,8-naphthalimide and cuprous iodide CuI (1.72g (9.04mmol), then add 40ml The organic solvent DMF, and finally add 2.54g (13.24mmol) of methyl fluorosulfonyl difluoroacetate. Under magnetic stirring, keep the temperature at 85-90°C for 20h to obtain the above-mentioned 4-trifluoromethyl-1,8-naphthalene Amine compounds;

[0051] After the reaction is completed, first filter to remove the insoluble matter, add ethyl acetate to the filtrate, then wash the organic phase with a large amount of water and saturated saline three times, then dry it with anhydrous sodium sulfate, and then carry out chromatography on a s...

Embodiment 2

[0059] A 4-trifluoromethyl-6-bromo-1,8-naphthalimide compound, the structural formula of which is as follows:

[0060]

[0061] where R 1 is n-butyl;

[0062] The reaction formula of its synthetic process is as follows:

[0063]

[0064] The concrete steps of its preparation method are as follows:

[0065] In a 50ml single-mouth bottle, add 1.0g (3.11mmol) of 4-trifluoromethyl-1,8-naphthalimide compound obtained in the above-mentioned Example 1, that is, N-n-butyl-4-trifluoroform Base-1,8-naphthalimide, 20ml concentrated sulfuric acid. Add 0.55g (3.11mmol) of N-bromosuccinimide (NBS) under ice bath and stir for 10min, remove the ice bath and continue to stir for 1h at room temperature, and track the reaction process with TLC until the reaction is complete;

[0066] After the reaction was completed, the reaction solution was poured into ice water, extracted with ethyl acetate, and then the organic phase was washed with saturated sodium bicarbonate solution, water and ...

Embodiment 3

[0074] A 4-trifluoromethyl-6-bromo-2-substituted acetonitrile-1,8-naphthalimide compound, the structural formula of which is as follows:

[0075]

[0076] where: R 1 is n-butyl; R 2 For phenyl.

[0077] The reaction formula of its synthetic process is as follows:

[0078]

[0079] The concrete steps of its preparation method are as follows:

[0080] Add 0.17g (1.41mmol) phenylacetonitrile, 0.28g (7.0mmol) base catalyst NaH (60w%) and tetrahydrofuran 25ml in the there-necked flask of 50ml, nitrogen replacement three times, add the 0.5g ( 1.25 mmol) of N-n-butyl-4-trifluoromethyl-6-bromo-1,8-naphthalimide continued to react at room temperature for 3 hours, and the reaction process was tracked by TLC until the reaction was complete;

[0081] After the reaction, the pH of the reaction liquid was adjusted to 1-2 with a saturated citric acid solution, and then extracted with ethyl acetate. The organic phase obtained was washed 3 times with saturated brine and then dried w...

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Abstract

The invention discloses 4-trifluoromethyl-6-bromo-2-substituted acetonitrile-1,8-naphthalimide compounds as well as a preparation method and an application thereof. The structural formula of the 4-trifluoromethyl-6-bromo-2-substituent acetonitrile-1,8-naphthalimide compounds is shown in the description, wherein R1 is an alkyl group of C1-C10 straight chains or branched chains; R2 is a phenyl group, a naphthyl group, a substituent phenyl group, a five-member or 6-member heteroaryl group or a benzo five-member or 6-member heteroaryl group. N-R1-1,8-naphthalimide compounds are used as initial materials, N-R1-4-trofluoromethyl-6-bromo-1,8-naphthalimide is obtained after trifluoromethylation and bromination and then reacts with R2 substituted acetonitrile under the alkali catalysis action, andthe compounds are obtained. The prepared 4-trifluoromethyl-6-bromo-2-substituted acetonitrile-1,8-naphthalimide compounds can be used as a colorimetric probe and a fluorescent probe for detecting cyanide ions.

Description

technical field [0001] The invention relates to a 4-trifluoromethyl-6-bromo-2-substituted acetonitrile-1,8-naphthalimide compound and a preparation method and application thereof, belonging to the technical field of organic photoelectric or fluorescent probes. Background technique [0002] Anion recognition, especially for cyanide ion recognition, has important applications in life, medicine, environment and other fields. The extremely toxic cyanide ions are very harmful to the environment. The cyanide ions ingested through drinking water will cause serious harm to the human body. At the same time, the detection of highly toxic cyanide ions has important applications in the environment and biological systems. . [0003] Color chemical sensors can convert molecular recognition information into easily perceived color signals, which are sensitive, fast and have low detection limits, and can be widely used in biochemistry, cell biology and analytical chemistry and other related...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C07D401/06C09K11/06G01N21/78G01N21/64G01N21/33G01N21/25
CPCG01N21/25G01N21/33G01N21/643G01N21/78C09K11/06C07D221/14C07D401/06C09K2211/1007C09K2211/1029
Inventor 刘传祥李喆垚饶才辉陈璐付超陈亚运朱婷婷
Owner SHANGHAI INST OF TECH
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