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Method for preparing high-purity cucurbit[10]uril

A gourd, high-purity technology, applied in the fields of organic synthesis and supramolecular chemistry, can solve the problems of difficult separation and purification, and few research reports

Inactive Publication Date: 2015-04-29
WUHAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although CB[10] exhibits very specific recognition properties, the research reports on it are the least. The reason is that it is not easy to separate and purify.

Method used

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  • Method for preparing high-purity cucurbit[10]uril
  • Method for preparing high-purity cucurbit[10]uril
  • Method for preparing high-purity cucurbit[10]uril

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1) Disperse glycoluril and paraformaldehyde in concentrated hydrochloric acid medium, the molar ratio of glycoluril and paraformaldehyde is 1:2, heat under reflux at 115°C for 9-12 hours, and let stand to cool; slowly pour the reaction solution under stirring In a solution with a water / methanol volume ratio of 1 / 6, stir for 2h to obtain a pale yellow precipitate, filter and dry to obtain a crude product of cucurbituril; repeatedly stir and wash with a large amount of water, and dry to obtain a crude product containing CB[5]CB[10] cucurbituril. product.

[0039] 2) Use one of the following two:

[0040] a. The obtained cucurbituril crude product is stirred, dissolved and filtered in 3M hydrochloric acid, repeated 2 to 3 times and the filtrate is collected; concentrated under reduced pressure, precipitated with methanol, and dried; the sample at this time has removed CB[5], CB[7] and a large amount of CB[8], the main components are CB[6], CB[5]CB[10], iCB[6] and a small ...

Embodiment 2

[0044] Disperse glycoluril and paraformaldehyde in a concentrated hydrochloric acid medium, the molar ratio of glycoluril and paraformaldehyde is 1:2, heat under reflux at 115°C for 9-12 hours, and let stand for cooling; slowly pour the reaction solution into water / water under stirring. In the solution with methanol volume ratio of 1 / 6, stir for 2h to obtain a pale yellow precipitate, filter and dry to obtain a crude product of cucurbituril; repeatedly stir and wash with a large amount of water, and dry to obtain a crude product containing CB[5]CB[10] cucurbituril.

[0045] The obtained cucurbituril crude product was stirred, dissolved and filtered in 3M hydrochloric acid, repeated 2 to 3 times and the filtrate was collected; concentrated under reduced pressure, precipitated with methanol, and dried; at this time, CB[5], CB[7] and a large amount of CB had been removed [8], the main components are CB[6], CB[5], CB[10], iCB[6] and a small amount of CB[8]. Then the processed cucu...

Embodiment 3

[0048] Dissolve pure CB[5]CB[10] (20.2mg) in 6M hydrochloric acid (1mL), add high concentration 3.5-dimethylamantadine hydrochloride (6.1mg, 3.5eq) aqueous solution, sonicate for 20 minutes, Let stand for 7-12 h; centrifuge, wash the precipitate with 2 mL of 6M hydrochloric acid and water twice in turn, and vacuum dry overnight to obtain 14.7 mg of a white solid with a yield of 96%.

[0049] Take pure CB[5]CB[10] and 3.5 equivalents of 3,5-dimethyladamantanamine hydrochloride in 20% deuterated hydrochloric acid (20% DCl / D 2 O) obtained after mixing ultrasonic 1 The H NMR spectrum is attached figure 1 shown. The spectra showed that all CB[10] precipitated with the guest to form insoluble inclusion complexes, so only free CB[5] and excess guest could be observed in H NMR spectra.

[0050] Take the CB[10] obtained in Example 1 at 20% DCl / D 2 in O 1 H NMR spectrum, see attached figure 2 shown. CB[10] is insoluble in water, but can be dissolved in a certain concentration of...

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Abstract

The invention discloses a method for preparing high-purity cucurbit[10]uril. The method comprises the following steps: reacting glycoluril and polyformaldehyde in a concentrated hydrochloric acid medium to obtain an insoluble solid containing cucurbit[5]uril@cucurbit[10]uril, and drying; dissolving the insoluble solid in 6M hydrochloric acid, adding a guest G water solution, carrying out ultrasonic oscillation, standing to obtain a white precipitate, and carrying out centrifugal drying to obtain a G@cucurbit[10]uril white solid; and putting the white solid in dimethyl sulfoxide, and removing the guest G in the G@cucurbit[10]uril white solid to obtain the high-purity cucurbit[10]uril. The prepared cucurbituril crude product is directly used for preparing the cucurbit[10]uril / guest inclusion compound, and the pure cucurbit[5]uril@cucurbit[10]uril can be obtained without using extremely hard purification. In addition, the guest is a cheap and accessible commercial product, and the removal of the guest in the subsequent process only needs simple extraction operation.

Description

technical field [0001] The invention belongs to the fields of organic synthesis and supramolecular chemistry, and in particular relates to a preparation method of high-purity cucurbit[10]uril in the cucurbituril family of a macrocyclic host compound. Background technique [0002] Cucurbituril was first prepared by Behrend's group in 1905 by polycondensation of glycoluril-formaldehyde under concentrated sulfuric acid, but its structure was not successfully identified at that time (Liebigs.Ann.Chem.1905,339,1). Until 1981, Mock's research group confirmed by X-ray single crystal diffraction method that the macrocyclic compound is a cyclic hexamer with glycoluril units bridged by methylene, and it was named Cucurbit because of its shape similar to that of cucurbits. [6]uril (CB[6]) (J.Am.Chem.Soc.1981,103,7367-7368), Chinese abbreviation is cucurbit[6]urea or cucurbit[6] ring. In 2000, Day and Kim's research group reported three other cucurbituril homologues-cucurbit[5]uril (CB...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C08G12/12
CPCC07D487/22C08G12/12
Inventor 刘思敏杨习然龚晚君
Owner WUHAN UNIV OF SCI & TECH