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Preparation method for polyglycol modified amphipathic calixarene

A technology of polyethylene glycol and calixarene, which is used in the preparation of ether, the preparation of ether by ester reaction, and organic chemistry, etc. problem, to achieve the effect of high yield and simple synthesis

Inactive Publication Date: 2009-02-18
SHANGHAI JIAO TONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this article only uses brominated short-chain polyethylene glycol to modify calix[6]arene and calix[8]arene. Due to the low reactivity of bromine-substituted polyethylene glycol, when the number of ethylene glycol units reaches 11 When the calix[6]arene and calix[8]arene polyethylene glycol derivatives are obtained, the yield is only 10%-40%
In this paper, the calixarene modified with polyethylene glycol whose end group is a hydroxyl group is synthesized in two steps. First, the hydroxyl group is protected with THP (tetrahydropyranyl), and then the calixarene is modified with polyethylene glycol and then deprotected. Lower yields obtained after two-step reaction

Method used

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  • Preparation method for polyglycol modified amphipathic calixarene
  • Preparation method for polyglycol modified amphipathic calixarene
  • Preparation method for polyglycol modified amphipathic calixarene

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Step a: In a 250 ml round bottom flask, add 5.2 g of end-methyl polyethylene glycol 550, 780 mg of sodium hydroxide, add 40 ml of water and stir to dissolve. 2.4 g of p-toluenesulfonyl chloride was dissolved in 40 ml of tetrahydrofuran, and the p-toluenesulfonyl chloride solution was added dropwise into the reaction flask with a constant pressure dropping funnel, and the addition was completed within 2 hours. After reacting in the refrigerator for 4 hours, the crude product was extracted with dichloromethane, and washed three times with deionized water to remove excess alkali, unreacted raw materials and by-products. When the molecular weight of polyethylene glycol is greater than 1000, it can be further purified by recrystallization from anhydrous ether. Final yield 85%.

[0025] Step b: In a 250 ml three-neck flask, add 1.29 g of tert-butylcalix[4]arene, 2.65 g of end-methyl polyethylene glycol 550, 559 mg of potassium carbonate, and 70 ml of anhydrous acetonitrile. ...

Embodiment 2

[0027] Step a: Step a: In a 250 ml round bottom flask, add 7.1 g of end-methyl polyethylene glycol 750, 780 mg of sodium hydroxide, add 50 ml of water and stir to dissolve. 2.4 g of p-toluenesulfonyl chloride was dissolved in 40 ml of tetrahydrofuran, and the p-toluenesulfonyl chloride solution was added dropwise into the reaction flask with a constant pressure dropping funnel, and the addition was completed within 2 hours. After reacting in the refrigerator for 4 hours, the crude product was extracted with dichloromethane, and washed three times with deionized water to remove excess alkali, unreacted raw materials and by-products. When the molecular weight of polyethylene glycol is greater than 1000, it can be further purified by recrystallization from anhydrous ether. The final yield was 78%.

[0028]Step b: In a 250 ml three-necked flask, add 1.29 g of tert-butylcalix[4]arene, 3.67 g of terminal methyl polyethylene glycol 750, then add 559 mg of potassium carbonate as a ca...

Embodiment 3

[0030] Step a: same as embodiment 1 step a

[0031] Step b: In a 250 ml three-necked flask, add 0.85 g of de-tert-butylcalix[4]arene, 2.65 g of end-methyl polyethylene glycol 550, 559 mg of potassium carbonate, and 70 ml of anhydrous acetonitrile. Stir to dissolve completely, and reflux for two days under nitrogen protection until the calixarene raw material disappears through thin-layer chromatography analysis. Add 20 ml of 0.1 mol / L sodium hydroxide solution and stir for two hours. Acetonitrile was distilled off under reduced pressure, and then 100 ml of ethyl acetate was added for extraction. After the ethyl acetate was evaporated to dryness, the product became a pale yellow oil, 2.8 g of the crude product, and the yield was 80%. The column was chromatographed on silica gel, eluting with dichloromethane / methanol=35:1 to 5:1 gradient, and after purification, 2.2 g of the product was obtained with a yield of 61%.

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Abstract

The invention discloses a method for preparing amphiphilic calixarene modified by polyethylene glycol, pertaining to the technical field of chemical engineering. Under low temperature and base catalysis, polyethylene glycol reacts with p-methyl benzene sulfonic chloride, one end is caused to reflect the previous p-methyl benzene sulfonic ester which is easy to move off. The achieved polyethylene glycol derivatives continue to react with the calixarene, the two hydroxyl groups at para positions are modified selectively, and finally the amphiphilic calixarene molecules are achieved. The yield of the two-step reaction is very high. Both the polyethylene glycol molecular weight and the end groups can be changed to achieve the selectively substituted amphiphilic calix[4]arene derivates. The amphiphilic features can be used to realize self-assembly in the solution, however, the remained two phenolic hydroxyl groups can be further functionalized. The amphiphilic calixarene derivatives (modified by polyethylene glycol) prepared by the method can be applied to drug transmission, gene transfection and other fields of biological medicine, as well as the fields of analog enzyme, phase catalysis, and the like.

Description

technical field [0001] The invention relates to a preparation method in the technical field of chemical industry, in particular to a preparation method of polyethylene glycol-modified amphiphilic calixarene. Background technique [0002] Calixarene and its derivatives can form complexes with organic molecules or metal ions. Therefore, calixarene is considered to be the third-generation supramolecular host molecule with more development potential after crown ether and cyclodextrin, and has been widely recognized in the field of host-guest chemistry. extensive research. Although some literatures have reported the application potential of calixarene in liquid film transport, complex extraction, molecular probes, molecular devices and sensors, there are not many calixarene and its derivatives with practical application value, among which One of the important reasons is that calixarene and its derivatives are small molecular organic compounds, which have disadvantages such as di...

Claims

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Application Information

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IPC IPC(8): C08G65/48C07C43/21C07C41/16
Inventor 余鑫朱新远屠春来王瑞斌蒋逸
Owner SHANGHAI JIAO TONG UNIV
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