Synthetic method and synthetic product of symmetric eight methyl cucurbit[6]uril

A technology of octamethyl six-membered melon and synthetic method, applied in the direction of organic chemistry, etc., can solve the problems of poor solubility, few research reports, hindering the development of melon ring chemistry, etc.

Inactive Publication Date: 2013-10-16
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the poor solubility of ordinary melon rings, especially six-membered melon rings and eight-membered melon rings in aqueous media and organic media, the development of melon ring chemistry is hindered.
Modified cucurbit rings can not only improve the solubility of cucurbit rings, but also make the cucurbit rings modifiable. It is a promising research direction in the field of cucurbit ring chemistry, but there are not many related research reports so far.

Method used

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  • Synthetic method and synthetic product of symmetric eight methyl cucurbit[6]uril
  • Synthetic method and synthetic product of symmetric eight methyl cucurbit[6]uril
  • Synthetic method and synthetic product of symmetric eight methyl cucurbit[6]uril

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Embodiment 1

[0021] Example 1: Weigh 9.1 grams of dimethylglycoside dimer and 3.6 grams of ordinary glycoluril, add them to 12 mol / L concentrated hydrochloric acid (60 mL), stir and dissolve completely, then add 3 grams of paraformaldehyde, Raise the temperature to 60°C, reflux for 7 hours, cool down, add water by rotary evaporation repeatedly to reduce the acidity of the system until a white powder solid appears, stand and filter, and the precipitate is washed with ice water and dried to obtain the target product—symmetric octamethylhexa melon ring.

Embodiment 2

[0022] Example 2: Weigh 9.1 grams of dimethylglycoside dimer and 3.6 grams of common glycoluril, add them to 12 mol / L concentrated hydrochloric acid (60 mL), stir and dissolve completely, then add 3 grams of paraformaldehyde, Raise the temperature to 70°C, reflux for 7 hours, cool down, add water by rotary evaporation repeatedly to reduce the acidity of the system until a white powder solid appears, stand and filter, and the precipitate is washed with ice water and dried to obtain the target product—symmetric octamethylhexa melon ring.

[0023] Dissolve this white solid in 6 mol / L hydrochloric acid, add appropriate amount of CdCl 2 (crystallization-inducing reagent), to obtain a symmetrical octamethyl six-membered cucurbit ring with [Cd 2 Cl 7 ] 3- Constructed supramolecular self-assemblies. Thus, the crystal structure of the symmetrical octamethyl six-membered melon ring was characterized. The crystal structure parameters are shown in Table 1.

[0024]

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PUM

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Abstract

The invention provides a synthetic method and a synthetic product of symmetric eight methyl cucurbit[6]uril, which are a synthetic method of organic chemistry macrocyclic supramolecular compounds symmetric eight methyl cucurbit[6]uril and a synthetic symmetric eight methyl cucurbit[6]uril. The symmetric eight methyl cucurbit[6]uril is formed by taking dimethyl replacing glycosides urea dimer, general glycoluril and paraformaldehyde as raw materials, replacing glycosides urea dimer with dimethyl through formaldehyde, and carrying out condensating selective formation between dimethyl and general glycoluril, so as to form the symmetric eight methyl cucurbit[6]uril. The invention discloses the synthetic method and a specific technology condition, and conducts sufficient structural characterization by analyzing measures such as nuclear magnetic resonance, single-crystal X-ray diffraction, mass spectrum, IR, and DSC-TG.

Description

technical field [0001] The invention discloses a new organic chemical macrocyclic compound and its synthesis and separation method, in particular, it is a synthesis and separation method of a compound named symmetrical octamethyl six-membered melon ring (OMeQ[6]). Background technique [0002] Cucurbit [n] uril (Cucurbit [ n ]urils), named melon rings for their resemblance to pumpkins [Latin Cucurbit]. Usually, cucurbitanyl is a kind of glycoside urea (structure such as figure 1 a) A class of macrocyclic compounds formed by the methylene bridge provided by formaldehyde, the reaction formula is as follows figure 1 shown. The structural characteristics of the hollow hydrophobic cavity of the melon ring form a unique melon ring host-guest chemistry, which involves catalysis, polymer chemistry, medicinal chemistry, biochemistry, life science, materials and other disciplines, and has become the mainstream research content of melon ring chemistry; The structural features of th...

Claims

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Application Information

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IPC IPC(8): C07D487/22
Inventor 尉鑫周加加赵迎春张前军薛赛凤祝黔江陶朱
Owner GUIZHOU UNIV
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