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Chirality covalent organic framework and synthesis method and application thereof

A covalent organic framework and synthesis method technology, applied in the field of chiral covalent organic framework materials and their synthesis, to achieve good catalytic activity and cycle stability, large specific surface area, and extended application effects

Active Publication Date: 2016-06-01
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although great efforts have been made, so far, no chiral molecular sieve has been successfully applied to chiral catalysis

Method used

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  • Chirality covalent organic framework and synthesis method and application thereof
  • Chirality covalent organic framework and synthesis method and application thereof
  • Chirality covalent organic framework and synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (1) The synthesis method of chiral precursor 1 is as follows:

[0035]

[0036] Synthesis of compound 3:

[0037] Take a one-necked bottle, add N-tert-butoxycarbonyl-L-proline (5.17g, 24.0mmol), anhydrous dichloromethane (60mL), stir to dissolve and cool to 0°C. Ethyl chloroformate (2.28mL, 24.0mmol) and anhydrous triethylamine (6.65mL, 48.0mmol) were slowly added dropwise, and then 3,6-dibromo-1,2-phenylenediamine (5.32g, 20.0 mmol). The reaction system was allowed to warm to room temperature, and the reaction was stirred at room temperature for 36h. After the reaction, 100 mL of water was added to the reaction system, extracted with dichloromethane, the organic phase was washed with saturated brine, dried with anhydrous sodium sulfate, and the solvent was evaporated to obtain a brown oil. Glacial acetic acid (25 mL) was added to the brown oil, and the reaction was stirred at 65° C. for 12 h. After the reaction, cool to room temperature, add saturated sodium car...

Embodiment 2

[0061] Add 8.1 mg of trimesaldehyde and 35.2 mg of chiral precursor 1 into the pressure-resistant tube. Then add 0.2mL absolute ethanol and 0.8mL mesitylene, shake well and add 0.10mL 3mol / L acetic acid solution. After sealing the pressure tube with a rubber stopper, replace it with argon three times, then quickly remove the rubber stopper, and seal the pressure tube with a polytetrafluoroethylene stopper. It was placed in an oven and reacted at 100° C. for three days. After the reaction, a solid was produced at the bottom of the pressure-resistant tube, and the solid was transferred to a centrifuge tube, washed with acetone and tetrahydrofuran for 3 times, respectively. Dry the solid at 100°C to obtain CCOF-LZU72-Boc.

[0062] CCOF-LZU72-Boc (15.0 mg) was placed in a pressure-resistant tube, replaced with argon three times, and then sealed with a polytetrafluoroethylene stopper. Place it in an oven preheated to 235°C and heat for 25 minutes to obtain CCOF-LZU72.

Embodiment 3

[0064] Add 16.2 mg of trimesaldehyde and 70.4 mg of chiral precursor 1 into the pressure tube. Then add 0.2mL tetrahydrofuran and 1.8mL mesitylene, shake well and add 0.4mL 3mol / L acetic acid solution. After sealing the pressure tube with a rubber stopper, replace it with argon three times, then quickly remove the rubber stopper, and seal the pressure tube with a polytetrafluoroethylene stopper. It was placed in an oven and reacted at 80° C. for three days. After the reaction, a solid was produced at the bottom of the pressure-resistant tube, and the solid was transferred to a centrifuge tube, washed with acetone and tetrahydrofuran for 3 times, respectively. Dry the solid at 100°C to obtain CCOF-LZU72-Boc.

[0065] CCOF-LZU72-Boc (15.0 mg) was placed in a pressure-resistant tube, replaced with argon three times, and then sealed with a polytetrafluoroethylene stopper. Place it in an oven preheated to 245°C, and heat it for 15 minutes to obtain CCOF-LZU72.

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Abstract

The invention discloses a synthesis method of a chirality covalent organic framework. The method includes the following steps that firstly, a chirality precursor and benzenetricarboxaldehyde are catalyzed by acetic acid under the inert atmosphere to react and generate a solid product, wherein the structural formula of the chirality precursor can be seen in the description, and Boc is t-butyloxycarboryl; secondly, t-butyloxycarboryl is removed from the solid product obtained in the first step to obtain the chirality covalent organic framework material. The chirality covalent organic framework is successfully synthesized, has a large specific area and a regular pore structure, has good catalytic activity and circulation for the asymmetric Aldol reaction of ketone and aldehyde, and is a good multiphase chirality catalyst, and the application range of the molecular sieve material in the field of chirality catalysis is greatly expanded.

Description

technical field [0001] The invention belongs to the field of organic functional materials, in particular to a chiral covalent organic framework material and its synthesis method and application. Background technique [0002] Chirality is a ubiquitous phenomenon in nature and plays a vital role in the origin of life and human life. Molecules with different chiral configurations may have significantly different biological activities, so obtaining optically pure chiral compounds is a very important research field. Asymmetric catalysis via chiral catalysts is the most effective way to obtain optically pure compounds. [0003] Existing studies have shown that L-proline and its derivatives have a good catalytic effect on the asymmetric Aldol reaction of ketones and aldehydes ("Asymmetric Aldol Condensation Reaction Catalyzed by Small Organic Molecules", Jiang Lijuan et al., Organic Chemistry, 2006 26, No. 5, pp. 618-626). However, L-proline and its derivatives are homogeneous c...

Claims

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Application Information

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IPC IPC(8): C07D403/04C07D403/14B01J31/06C07B53/00
CPCB01J31/061B01J2231/4205C07B53/00C07B2200/07C07D403/04C07D403/14
Inventor 王为许海森丁三元
Owner LANZHOU UNIVERSITY
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