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Preparation method of methylene bridged cucurbituril

A technology of methylene bridge uride and methylene bridge is applied in the field of preparation of methylene bridge cucurbituril, which can solve the problem of poor stability of methylene bridge cucurbituril, inability to separate, and yield of methylene bridge cucurbituril. Low problems, to achieve the effects of low cost, reduced preparation cost, and simplified reaction

Inactive Publication Date: 2017-08-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, studies have shown that methylene cucurbituril has poor stability under acidic conditions. Although some researchers have tried to condense it with formaldehyde to form a ring, the analysis shows that the yield of the by-product, methylene cucurbitacil, is extremely low. could not be isolated from the product

Method used

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  • Preparation method of methylene bridged cucurbituril

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Put methylene glucoside urea (10g, 64mmol), paraformaldehyde (5g, 167mmol) and calcium chloride (0.5g, 4.5mmol) in a reaction flask, add 5mL of water and 15mL of hydrochloric acid, stir and heat up to 100°C , reacted for 8 hours, a white solid was precipitated, and filtered to obtain the product methylene cucucurbit[4]urea, which was dried to obtain 3.61 g with a yield of 31.3%.

[0033] The chemical shift value of the product in the NMR spectrum is: 1 H NMR (400MHz,D 2 O, ppm) δ: 6.36 (d, 8H, J=16), 5.23 (s, 8H), 4.19 (d, 8H, J=16), 2.32 (s, 8H).

[0034] The molecular weight of the compound obtained by high-resolution mass spectrometry is: m / z calculate for [C 28 h 32 N 16 o 8 +H + ]:721.26,found:721.26.

Embodiment 2

[0036] Place methylene urea (10g, 64mmol), paraformaldehyde (5g, 167mmol) and calcium chloride (1g, 9mmol) in a reaction flask, add 5mL of water and 15mL of hydrochloric acid, stir and heat up to 100°C, react After 8 hours, a white solid was precipitated, filtered to obtain the product methylene cucurbit[4]urea, and after drying, 6.22g was obtained after drying, with a yield of 54.08%

[0037] The chemical shift value of the product in the NMR spectrum is: 1 H NMR (400MHz,D 2 O, ppm) δ: 6.36 (d, 8H, J=16), 5.23 (s, 8H), 4.19 (d, 8H, J=16), 2.32 (s, 8H).

[0038] The molecular weight of the compound obtained by high-resolution mass spectrometry is: m / z calculate for [C 28 h 32 N 16 o 8 +H + ]:721.26,found:721.26.

Embodiment 3

[0040] Place methylene glucoside urea (10g, 64mmol), paraformaldehyde (5g, 167mmol) and calcium nitrate (1.5g, 9mmol) in a reaction flask, add 5mL of water and 15mL of hydrochloric acid, stir and heat up to 100°C, and react 8h, a white solid was precipitated, filtered to obtain the product methylene cucurbit[4] urea, and after drying, 3.22g was obtained, with a yield of 28%

[0041] The chemical shift value of the product in the NMR spectrum is: 1 H NMR (400MHz,D 2 O, ppm) δ: 6.36 (d, 8H, J=16), 5.23 (s, 8H), 4.19 (d, 8H, J=16), 2.32 (s, 8H).

[0042] The molecular weight of the compound obtained by high-resolution mass spectrometry is: m / z calculate for [C 28 h 32 N 16 o 8 +H + ]:721.26,found:721.26.

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Abstract

The invention relates to a preparation method of methylene bridged cucurbituril. The preparation method comprises the following steps: synthesizing 1,1,3,3-malonaldehyde tetramethyl acetal and urea into methylene bridged glycoluril at first; then feeding the methylene bridged glycoluril, paraformaldehyde and calcium salt or barium salt into a mixed solution of water and hydrochloric acid, reacting and refluxing, wherein the mass ratio of the methylene bridged glycoluril to formaldehyde is 1: (0.4-1), the volume ratio of the water to the hydrochloric acid is 1: (1-3), the ratio of the mass of the methylene bridged glycoluril to the volume of the hydrochloric acid is 1: 1-3, the mass ratio of the methylene bridged glycoluril to the calcium salt is 1: 0.05-0.4, and the mass ratio of the methylene bridged glycoluril to the barium salt is 1: 0.1-0.3; and carrying out cooling, suction filtration and washing to obtain the methylene bridged cucurbituril [4] or the methylene bridged cucurbituril [5]. The methylene bridged cucurbituril [4] and the methylene bridged cucurbituril [5] are synthesized in an oriented manner by using metal salt as a template, the method is simple and convenient, a purification process is simple, and the yield is obviously increased.

Description

[0001] Technical field: [0002] The present invention relates to a preparation method of methylene bicucurbituril, in particular to a method for synthesizing methylene bicucurbit [4] urea and cucurbit [5] urea by using metal ions as templates. Background technique [0003] Cucurbituril is a series of cyclic compounds formed by the cyclization of glycoside urea and formaldehyde under acidic conditions. Its two ends are hydrophilic carbonyl groups, while the inner cavity is hydrophobic. Cucurbituril, as a new type of artificially synthesized cyclic compound after crown ether, cyclodextrin and calixarene, has the advantages of good stability and rigid structure, and can include many small molecules and positively charged substances, so in supramolecular , Molecular machines, new materials, catalytic reactions and even life medicine and other fields have important applications. However, there are more or less problems in the synthesis of cucurbituril and its analogues. For exam...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 王巧纯沈叶楠化浩杰徐红星田禾
Owner EAST CHINA UNIV OF SCI & TECH
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