A class of coumarin hydrazone compound, its preparation method and application
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A compound, coumarin technology, applied in chemical instruments and methods, organic chemistry, material excitation analysis, etc., can solve the problems of disturbing endogenous formaldehyde concentration, slow detection response, poor sensitivity, etc.
Active Publication Date: 2021-04-27
ZHEJIANG UNIV
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At present, only a small number of fluorescent probes for formaldehyde detection have been reported, and most of them have the problems of slow detection response and poor sensitivity, and some formaldehyde will be consumed while detecting formaldehyde, thereby disturbing the concentration of endogenous formaldehyde in biological samples
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Embodiment 1
[0055]Example 1: Preparation of I-1
[0056]
[0057]Compound I-1A and Lawson reagents reflow in dried toluene. The reaction ends, cooling filtration, filtration, and dissolved in ethanol after drying solvent, 80% hydrated hydrazine, reflow reaction. After the reaction was completed, the carnivore was added, and the water was added three times with dichloromethal, combined with an organic phase, sodium anhydrous sodium sulfate, and purified, gave I-1 (yield 65%). LC-MS: M / Z 256.145 [M + H]+.
Embodiment 2
[0058]Example 2: Preparation of II-1
[0059]
[0060]Compound II-1A and Lawsen reagents reflow in dry toluene. The reaction ends, cooling filtration, filtration, and dissolved in ethanol after drying solvent, 80% hydrated hydrazine, reflow reaction. After the reaction was completed, the carnifened solvent was added, and the water was added three times with dichloromethydehyde, and the organic phase, sodium alhydrate sodium sulfate was combined, and the column chromatography was purified to give II-1 (yield 68%). LC-MS: M / Z254.1293 [M + H]+.
Embodiment 3
[0061]Example 3: Preparation of II-2
[0062]
[0063]Compound II-2A and Lawn reagents reflow in dry toluene. The reaction ends, cooling filtration, filtration, and dissolved in ethanol after drying solvent, 80% hydrated hydrazine, reflow reaction. After the reaction was completed, the carnifecene was added, and the water was added three times, and the organic phase, dried over anhydrous sodium sulfate was combined, and the column chromatography was purified to give II-2 (yield 73%). LC-MS: M / Z296.1340 [M + H]+.
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Abstract
The present invention relates to a class of coumarin hydrazone compound selected from the following compounds, its preparation method and application. The coumarin hydrazone compound or its salt itself of the present invention has only weak fluorescence, but it can specifically and quickly react with formaldehyde to generate a product with strong fluorescence, and there is a linear correlation between the fluorescence intensity and the concentration of formaldehyde, thereby realizing the specificity to formaldehyde Sex detection and quantitative analysis. The coumarin hydrazone compound or its salt of the present invention is suitable for the determination of formaldehyde content in the environment, the labeling and imaging of formaldehyde in cells and tissues, the determination of formaldehyde content in biological samples such as tissue homogenate, plasma, urine, saliva, etc., and food Determination of formaldehyde content in life samples such as cosmetics, clothing and so on.
Description
Technical field[0001]The present invention is an environmentally analyzed chemistry and biological detection field, which relates to a class of coumarin 腙 compounds, which are prepared as a method of detecting fluorescent probe molecules in formaldehyde, in the detection environment and the formaldehyde content in the detection environment.Background technique[0002]Formaldehyde is a colorless gas, there is a special stimulating odor, and there is a stimulating effect on human eye, nose. The high concentration of formaldehyde in the environment is sensitized, teratogenic and carcinogenic to the human body, and formaldehyde is thus determined in 2006 to be 1 category carvino. Therefore, in the detection environment, especially furniture, new decoration space, new clothes material, and even formaldehyde content in food is an important and practical work.[0003]The toxicity of high concentration formaldehyde in the environment has been in-depth study at home and abroad. In contrast, in r...
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