6-site monosubstituted-beta-cyclodextrin functional monomer and preparation method thereof

A technology of functional monomers and cyclodextrins, applied in mono-))-)-6-deoxy)-β-cyclodextrin functional monomers and its preparation, 6-position monosubstituted-β-cyclodextrin functional In the field of monomer and its preparation, it has achieved a wide range of research effects

Inactive Publication Date: 2014-09-10
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no commercial β-cyclodextrin functional monomer, and the development of cyclodextrin functional monomer that is easy to obtain and has excellent solubility can make up for the shortage of existing functional monomers

Method used

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  • 6-site monosubstituted-beta-cyclodextrin functional monomer and preparation method thereof
  • 6-site monosubstituted-beta-cyclodextrin functional monomer and preparation method thereof
  • 6-site monosubstituted-beta-cyclodextrin functional monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: This single-(6-ethylenediamine-( N -(2-bis(3-allyloxy-2-hydroxy-propyl)))-( N -(3-allyloxy-2-hydroxy-propyl))-6-deoxy)-β-cyclodextrin (IV), its structural formula is as follows:

[0036] ;

[0037] Its specific preparation process is as follows:

[0038] (1) Synthesis of mono-(6-p-methylbenzenesulfonyl-6-deoxy)-β-cyclodextrin (Ⅱ)

[0039]

[0040] Take 17.22 g (0.0150 mol) of β-cyclodextrin (I) in a 250 mL round bottom flask, add 200 mL of 0.30 mol / L sodium hydroxide solution, stir to dissolve, add dropwise 1.45 g (0.00750 mol) of p-toluenesulfonyl chloride Acetonitrile solution 5.5 mL, dropwise time is 5 min, reaction temperature is 10 °C, after reaction for 2 h, filter after completion of the reaction, adjust pH = 1 with hydrochloric acid, store in refrigerator at 4 °C overnight, a large amount of precipitate precipitates, filter, re- Crystallized to obtain a white solid, which was dried under vacuum at 40°C for 5 h to obtain mono-(6-p-toluenesu...

Embodiment 2

[0047] Embodiment 2: This single-(6-ethylenediamine-( N -(2-bis(3-allyloxy-2-hydroxy-propyl)))-( N -(3-allyloxy-2-hydroxy-propyl))-6-deoxy)-β-cyclodextrin (IV), its structural formula is as follows:

[0048] ;

[0049] Its specific preparation process is as follows:

[0050] (1) Synthesis of mono-(6-p-methylbenzenesulfonyl-6-deoxy)-β-cyclodextrin (Ⅱ)

[0051] Take 17.22 g (0.0150 mol) of β-cyclodextrin (I) in a 250 mL round bottom flask, add 200 mL of 0.25 mol / L sodium hydroxide solution, stir to dissolve, add dropwise 2.90 g (0.0150 mol) of p-toluenesulfonyl chloride The acetonitrile solution was 11 mL, and the dropping time was 10 min. After reacting for 3 h, the reaction temperature was 20°C. After the reaction was completed, it was filtered, adjusted to pH = 2 with hydrochloric acid, and stored in the refrigerator at 4°C overnight. A large amount of precipitate was precipitated, filtered, Recrystallized to obtain a white solid, which was dried in vacuum at 40°C for 5...

Embodiment 3

[0068] Embodiment 3: This single-(6-ethylenediamine-( N -(2-bis(3-allyloxy-2-hydroxy-propyl)))-( N -(3-allyloxy-2-hydroxy-propyl))-6-deoxy)-β-cyclodextrin (IV), its structural formula is as follows:

[0069] ;

[0070] Its specific preparation process is as follows:

[0071] (1) Synthesis of mono-(6-p-methylbenzenesulfonyl-6-deoxy)-β-cyclodextrin (Ⅱ)

[0072] Take 17.22 g (0.0150 mol) of β-cyclodextrin (I) in a 250 mL round bottom flask, add 200 mL of 0.20 mol / L sodium hydroxide solution, stir to dissolve, add dropwise 5.80 g (0.0300 mol) of p-toluenesulfonyl chloride Acetonitrile solution was 20 mL, and the dropwise addition time was 15 min. After reacting for 4 h, the reaction temperature was 30°C. After the reaction was completed, filter, adjust the pH to 3 with hydrochloric acid, and store in the refrigerator at 4°C overnight. Crystallized to obtain a white solid, which was dried in vacuum at 40°C for 5 h to obtain mono-(6-p-toluenesulfonyl-6-deoxy)-β-cyclodextrin (I...

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Abstract

The invention discloses a 6-site monosubstituted-beta-cyclodextrin functional monomer and a preparation method thereof, and belongs to the supramolecular chemistry and functional high-molecular polymer intermediate synthesis technical fields. The preparation method comprises the steps: with beta-cyclodextrin as raw material, firstly, deriving p-toluenesulfonyl chloride, synthesizing mono-(6-p-toluenesulfonyl-6-deoxy)-beta-cyclodextrin, then adopting ethylenediamine as a reaction reagent, synthesizing mono-(6-ethylenediamine-6-deoxy)-beta-cyclodextrin, finally adopting allyl glycidyl ether as a derivatization reagent, and synthesizing mono-(6-ethylenediamine-N-(2-(bis(3-allyloxy-2-hydroxy-propyl)))-(N-(3-allyloxy-2-hydroxy-propyl))-6-deoxy)-beta-cyclodextrin. The structure of mono-(6-ethylenediamine-N-(2-(bis(3-allyloxy-2-hydroxy-propyl)))-(N-(3-allyloxy-2-hydroxy-propyl))-6-deoxy)-beta-cyclodextrin synthesized by the method contains terminal vinyl, can be used as an extremely valuable functional monomer in high-molecular polymer preparation, and is used for selective molecular recognition of guest molecules.

Description

technical field [0001] The invention belongs to the technical field of supramolecular chemistry and functional polymer intermediate synthesis, and relates to a 6-position monosubstituted-β-cyclodextrin functional monomer and a preparation method thereof, in particular to a mono-(6-ethylene di amine-( N -(2-bis(3-allyloxy-2-hydroxy-propyl)))-( N -(3-allyloxy-2-hydroxy-propyl))-6-deoxy)-β-cyclodextrin functional monomer and its preparation method. Background technique [0002] β-cyclodextrin is a cyclic oligosaccharide composed of D-glucopyranose units connected by a-(1-4)-glycosidic bonds, with a degree of polymerization of 7, and its molecular structure is in the shape of a circular platform. The structural formula is as follows : [0003] [0004] β-cyclodextrin is hydrophilic outside the ring and hydrophobic inside the ring. Its ring cavity not only has many chiral recognition sites, but also can include different compounds, such as organic molecules, rare gases, ino...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16
Inventor 许志刚冯锋汤令刘智敏
Owner KUNMING UNIV OF SCI & TECH
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