Preparation method and application of azobenzene diamido bridged beta-cyclodextrin chiral stationary phase

A technology of azophthalamide-based bridges and chiral stationary phases, which can be used in separation methods, chemical instruments and methods, and other chemical processes, and can solve problems such as port group crowding and inconvenient cavity inclusions , to achieve the effect of good reproducibility, low cost of raw materials and simple process

Active Publication Date: 2021-04-06
NANCHANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the derivatization of the port makes the port group crowded to a certain

Method used

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  • Preparation method and application of azobenzene diamido bridged beta-cyclodextrin chiral stationary phase
  • Preparation method and application of azobenzene diamido bridged beta-cyclodextrin chiral stationary phase
  • Preparation method and application of azobenzene diamido bridged beta-cyclodextrin chiral stationary phase

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0028]Example 1

[0029](1) Azo-4,4'-dimethic acid (mmol): mono-6-amino-beta-cyclodextrin (mmol): N, N'-bicyclic hexyl carbonimide (DCC, mmol : 1-hydroxybenzene triazole (HOBT, Mmol): N, N-dimethylformamide (DMF, mL) is mixed at a ratio of 1.0: 1.5: 1.5: 1.5: 15, at normal temperature for 48h, resulting in even The solution of a nitroenenenenenenenenenenenenenenenenenenenenenenenenenzide-based bridge, acetone, and acetone, acetone, precipitation, filtration, and solid water, separated purification by carboxymethyl glucangel (C-25) column. Elite is added with acetone, dried to give azobenzene-4,4'-dimethamide-based bridge β-cyclodextricular ligand;

[0030](2) Under nitrogen protection, the azobenzothylene terephthalamide-based bridge is dissolved in anhydrous DMF, and then 0.4 ml of γ-isocyanate-propylene triethoxysilane is slowly added to the above. The solution was reacted at 80 ° C for 2 h to give the reaction solution of the azo-4,4'-dimethamide-containing bridge β-cyclodextrial ethox...

Example Embodiment

[0035]Example 2

[0036](1) Azo-4,4'-dimethic acid (mmol): mono-6-amino-β-cyclodextrin (mmol): DCC (mmol): hobt (mmol): DMF (ml) Press 1.0 : 2.0: 2.0: 2.0: 20 is mixed, at room temperature for 48 h, resulting in a solution of azobenzothyldimide-based bridge β-cyclodextride, acetone is added to the above reaction liquid, and precipitate, filtrate, solid water dissolved Purification purification by a carboxymethyl glucangel (C-25) column, eluent, adding acetone, dried to obtain azobenzene-4, 4'-dimetamide bridge 1 β-cyclodextrin Chiral ligand;

[0037](2) Under nitrogen protection, the azobenzothylene terephthalamide-based bridge is dissolved in anhydrous DMF, and then 0.4 ml of γ-isocyanate-propylene triethoxysilane is slowly added to the above The solution was reacted at 80 ° C for 2 h to give the reaction solution of the azo-4,4'-dimethamide-containing bridge β-cyclodextrial ethoxysilane;

[0038](3) Under nitrogen protection, the azobenyldime (mmol) of (2) in (2) is 1: 3.5, the dry SBA- 15...

Example Embodiment

[0042]Example 3

[0043](1) Azo-4,4'-dimethic acid (mmol): mono-6-amino-β-cyclodextrin (mmol): DCC (mmol): hobt (mmol): DMF (ml) Press 1.0 The ratio of 2.5: 2.5: 2.5: 25 was mixed, at normal temperature for 48 h, resulting in a solution of azobenzene terephthalamide bridge β-cyclodextrin, and acetone was added to the above reaction liquid precipitation, filtered, solid water dissolved Purification purification by a carboxymethyl glucangel (C-25) column, eluent, adding acetone, dried to obtain azobenzene-4, 4'-dimetamide bridge 1 β-cyclodextrin Chiral ligand;

[0044](2) Under nitrogen protection, the azobenzothylene terephthalamide-based bridge is dissolved in anhydrous DMF, and then 0.4 ml of γ-isocyanate-propylene triethoxysilane is slowly added to the above The solution was reacted at 80 ° C for 2 h to give the reaction solution of the azo-4,4'-dimethamide-containing bridge β-cyclodextrial ethoxysilane;

[0045](3) Under nitrogen protection, the azobenyldime (mmol) of (2) in (2) is 1: 3.5...

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Abstract

The invention relates to the technical field of chiral stationary phases, in particular to a preparation method and an application of an azobenzene diamido bridged beta cyclodextrin chiral stationary phase. The azobenzene diamido bridged beta cyclodextrin is used as a second-generation supramolecular compound, azobenzene provides pi pi-pi action, amide is a hydrogen bond donor and also a hydrogen bond receptor, azo has a flexible structure, cooperation with a synergistic inclusion effect between two cyclodextrin cavities is facilitated, and the stability of the supramolecular compound is improved. The surface of a stationary phase prepared from the bridged cyclodextrin contains rich action sites, so that the spatial structure difference of levorotatory and dextrorotatory enantiomers can be comprehensively identified, more chiral substances can be split in a short time, the chiral separation efficiency is greatly improved, the method can be applied to normal-phase, reversed-phase and polar organic modes, the splitting range is widened, and good practical values are realized.

Description

technical field [0001] The invention relates to the technical field of chiral stationary phases, in particular to a preparation method and application of an azobenzenedicarboxamido bridged β-cyclodextrin chiral stationary phase. Background technique [0002] Chirality is a common phenomenon in nature, and chiral compounds are widely used in chemistry, medicine, food, pesticides, etc. According to authoritative research, among 1800 kinds of pesticides, 57% of active ingredients are chiral. The chirality problem caused by enantiomers has attracted widespread attention from the international community at the beginning of the 20th century. The blood lessons of the "thalidomide incident" have made people start to be vigilant and gradually realize that although the physical and chemical properties of enantiomers The properties are almost the same, but they may exhibit completely different biological activities, toxicity, toxicology, metabolic pathways and medicinal value when int...

Claims

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Application Information

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IPC IPC(8): B01J20/29B01J20/30B01D15/38
CPCB01J20/29B01D15/3833
Inventor 李来生张天赐钟慧双亚洲李良
Owner NANCHANG UNIV
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