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Synthesis method of novel fluorescent functional molecule glycoluril benzylamine carboxylic acid derivative

A technology of molecular glycoluril benzylamine carboxylic acid and glycoluril benzylamine carboxylic acid, which is applied in the field of synthesis of fluorescent functional small molecule compounds, can solve problems such as inconvenient operation, limitations, and poor water solubility of molecular tweezers, and achieve cost reduction and product yield High and mild reaction conditions

Pending Publication Date: 2022-03-04
YUNNAN OPEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, at present, when studying the recognition of glycoluril host and guest molecules, the analysis method of nuclear magnetic titration is mainly used, so the operation is inconvenient
Although there are also a few reports on molecular tweezers of glycoluril with fluorescent properties, these molecular tweezers are often poorly soluble in water, and their applications in the detection of metal ions are limited.

Method used

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  • Synthesis method of novel fluorescent functional molecule glycoluril benzylamine carboxylic acid derivative
  • Synthesis method of novel fluorescent functional molecule glycoluril benzylamine carboxylic acid derivative
  • Synthesis method of novel fluorescent functional molecule glycoluril benzylamine carboxylic acid derivative

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Experimental program
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Embodiment 1

[0030] The synthetic method of Tetramethylol glycoluril, its step is as follows:

[0031] S1: Add 7.1g glycoluril, 8.9g paraformaldehyde, 25ml distilled water to the three-necked flask, and then add 1M Na 2 CO 3 Adjust the pH value to 9-10, raise the reaction temperature to 45°C, and react for 2 hours;

[0032] S2: After the reaction of S1 is completed, the reactant is cooled to room temperature, concentrated under reduced pressure to a viscous state; 40ml of methanol is added, and stirred for 4 hours by a magnetic stirrer, and solids continue to precipitate during the stirring process;

[0033] S3: The solid precipitated in S2 was suction-filtered, and the filter cake was washed with a small amount of methanol, and vacuum-dried to obtain 5.92 g of white solid, which was tetramethylol glycoluril, and the calculated yield was 45.2%;

[0034] The infrared, NMR, carbon, and mass spectrometry data of tetramethylol glycoluril are:

[0035] IR(KBr)υ(cm-1)=3467,3298,2957,1723,1490...

Embodiment 2

[0039] The synthetic method of glycoluril benzylamine carboxylic acid derivative, its step is as follows:

[0040] S4: Take 1.31g of tetramethylol glycoluril prepared in Example 1, 1.63g of p-benzylaminobenzoic acid, and 20ml of distilled water were added to a 100ml three-necked flask, stirred with a magnetic stirrer, heated to 45°C, and obtained White suspension, add NaOH to adjust the pH to 8-9, the solution gradually becomes clear, continue heating to 950°C, react for 2.5h, stop heating, and cool to room temperature;

[0041] S5: Add HCl to the reaction solution at room temperature in S4 to adjust the pH to 5-6, and a white solid precipitates out. After filtration, take a white solid filter cake, wash the filter cake with methanol and water respectively, and vacuum dry to obtain 0.9033 g of a white solid, namely It is a glycoluril benzylamine carboxylic acid derivative with a yield of 36.7%.

[0042] The infrared, NMR, carbon, and mass spectrometry data of glycoluril benzy...

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Abstract

The invention discloses a synthesis method of a novel fluorescent functional molecule glycoluril benzylamine carboxylic acid derivative, which comprises the following steps: reacting glycoluril with formaldehyde to obtain tetrahydroxymethyl glycoluril, and carrying out condensation reaction on tetrahydroxymethyl glycoluril and p-benzylbenzoic acid to form a ring, thereby obtaining the fluorescent functional molecule glycoluril benzylamine carboxylic acid derivative. And finally, separating and purifying to obtain a novel compound, namely the glycoluril benzylamine carboxylic acid derivative, which belongs to a fluorescent functional molecular substance and can be applied to preparation of fluorescent substances or materials. Compared with existing synthesis of similar substances, the synthesis method has the advantages that raw materials are simple and easy to obtain, reaction conditions are mild, environmental pollution is small, and the yield of target products is high.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fluorescent functional small molecule compounds, and in particular relates to a synthesis method of novel fluorescent functional molecule glycoluril benzylamine carboxylic acid derivatives. Background technique [0002] Glycoluril has a rigid bicyclic nest structure, two hydrophilic carbonyl groups that can be used as ion binding sites, four N-H bonds with strong reactivity, and two modifiable bridging C atoms. Therefore, since its synthesis in 1877, become the subject of extensive research. The synthesis method of glycoluril is simple and highly modifiable. Various derivatives synthesized after nitration, condensation, substitution, and hydroxymethylation have been widely used in the research of energetic materials, molecular recognition, and molecular capsules. Therefore, Glycoluril molecular tweezers have great application prospects in molecular recognition and self-assembly research. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C09K11/06G01N21/64
CPCC07D487/22C09K11/06G01N21/643C09K2211/1074
Inventor 朱超黄遥唐芳周明善桂艳刘华戎杨景成
Owner YUNNAN OPEN UNIV
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