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Melon ring and method of synthesizing substituted melon ring

A synthetic method, the technology of cucurbit rings, applied in the field of compound synthesis, can solve problems such as effective control of the number and position of substituents, difficulty in obtaining products containing only part of substituents, difficult substitution of cucurbit rings, etc.

Inactive Publication Date: 2008-01-23
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] When using the above-mentioned method to synthesize the melon ring, there are two difficulties
One is that when synthesizing ordinary cucurbit rings, the obtained product is a mixture of various cucurbit rings, and the mixture contains Q[5], Q[6], Q[7], Q[8], Q[10], etc. , it is difficult to effectively control the distribution of various cucurbit rings in the product during synthesis; second, when synthesizing substituted cucurbit rings, usually only the product in which the hydrogen on the cucurbit ring is completely substituted can be obtained, and it is difficult to obtain a product containing only part of the substituents. product, which is difficult to effectively control the number and position of substituents in the substituted cucurbit ring

Method used

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  • Melon ring and method of synthesizing substituted melon ring
  • Melon ring and method of synthesizing substituted melon ring
  • Melon ring and method of synthesizing substituted melon ring

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Example 1: In a 250mL round bottom flask filled with concentrated hydrochloric acid (40mL), add dimethyl-substituted epoxy glycoluril (4.0g, 20mmol), glycoluril dimer (8.0g, 26mmol), diglycoside The ratio of the amount of the polymer to the substance of the dimethyl-substituted epoxyglycoside is 1.3:1, and potassium chloride (2.0 g, 26 mmol) is heated under reflux under stirring for 2 hours. After the obtained dark red solution was cooled to room temperature, light red crystals (mainly composed of potassium chloride) appeared, and the crystals were filtered. After the filtrate was concentrated on a rotary evaporator to remove hydrochloric acid, 10 g of mixed cucurbit rings was obtained with a yield of 85%. Add 500mL of water to the crude product to dissolve the soluble melon ring in the mixture. The eluate was concentrated and recrystallized with distilled water to obtain 6.0 g of hexamethylpentaquinone (HMeQ[5]), with a yield of 49%. The precipitate was recrystallize...

Embodiment 2

[0035]Embodiment 2: take by weighing 2g dimethyl epoxidized glycoluril and 3.62g glycoluril dimer (its mol ratio is 1: 1), and lithium chloride (as template reagent) 0.5g, join in 19ml 36% In the hydrochloric acid solution, stir at room temperature until the reactants are completely dissolved (about 1 hour), the reaction solution turns dark red, and then heated to 90-100 ° C for 2 hours, after the obtained dark red solution is cooled to room temperature, crystals appear 1:1), and lithium chloride (as a template reagent) 0.5g, was added to 19ml of 36% hydrochloric acid solution, stirred at room temperature until the reactants were completely dissolved (about 1 hour), the reaction solution turned dark red, and then heated React at 90-100°C for 2 hours, and after cooling the resulting dark red solution to room temperature, crystals (mainly composed of lithium chloride) appear. The crystal filtration reaction solution was evaporated to dryness with a rotary evaporator to obtain 4....

Embodiment 3

[0036] Embodiment 3: in the hydrochloric acid solution of 60ml 36%, glycoside uride dimer 12.0g, lithium chloride (as template reagent) 7.5g, paraformaldehyde 1.3g, the substance of glycoside uride dimer and paraformaldehyde The amount ratio is 1:1.11. After dissolved under stirring, heat to reflux under stirring at 100°C for 2 hours, cool the obtained solution to room temperature, and filter. After the filtrate was concentrated on a rotary evaporator to remove most of the hydrochloric acid, the clear solution obtained by suction filtration and the filtrate standing still crystallized to obtain 11 g of crude melon ring product with a yield of 88%. The crude product of mixed cucurbit rings is dissolved in as little as possible 2mol / L HCl eluent, and is separated by column chromatography (chromatographic column: chromatography silica gel 500g, column length L=30cm, column diameter R=5cm), to obtain Six-membered melon ring (Q[6]) 9.0g and eight-membered melon ring (Q[8]) 1.1g. T...

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Abstract

The invention relates to a cucurbituril and a synthetic method replacing the cucurbituril, which is an organic chemical heterocyclic compound, in particular to a compound named cucurbituril and a synthetic method replacing the cucurbituril. The synthetic method is that the glycolurils dimer is used as raw material and is heated and reacted with the epoxy glycolurils or the epoxy glycolurils derivatives and the formaldehyde in the hydrochloric acid medium under 90 DEG C. to 100 DEG C. for 1h to 2h; the cucurbituril is gained after condensation, filtration, separation and purification. The mixture is calculated based on the quantity of the material, and the glycolurils dimer : epoxy glycolurils or epoxy glycolurils derivatives : formaldehyde equals to 1 : 0 to 4 : 0 to 4, wherein, the epoxy glycolurils or epoxy glycolurils derivatives and the formaldehyde can not be zero at the same time, and the concentration of the hydrochloric acid is 3mol / L to 12mol / L. The invention can overcome the defect that the distribution of the cucurbituril in the product and the quantities and position of the substituent in the cucurbituril in the traditional synthetic method of the cucurbituril are difficult to control.

Description

Technical field: [0001] The invention is an organic chemical heterocyclic compound, specifically a method for synthesizing a compound named cucurbit ring and a substituted cucurbit ring. Background technique: [0002] Melon rings (recorded as Q[n], structural formula shown in Figure 1) are also known as Cucurbit[n]urils (Cucurbit[n]urils), named for their resemblance to pumpkins (Latin: Cucurbit). Denoted as A, the structure shown in Figure 2) is a new type of macrocyclic compound formed by methylene bridging. In 1905, Behrend et al first prepared and synthesized cucurbit rings with a degree of polymerization of 6 (ie, six-membered cucurbit rings, Cucurbit[6] urils) through a simple reaction between urea, glyoxal and formaldehyde. Its structure was not recognized until 1981. Determined by Freeman et al. by crystal structure determination. In order to indicate the number of structural units of the glycoside uridine ring in the cucurbit ring, the naming rule similar to that ...

Claims

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Application Information

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IPC IPC(8): C07D487/22
Inventor 薛赛凤祝黔江陶朱
Owner GUIZHOU UNIV
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