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A kind of chitosan/polyvinyl alcohol composite membrane supported nano-copper catalyst and its application

A polyvinyl alcohol and catalyst technology, which is applied in the field of chitosan/polyvinyl alcohol composite membrane-supported nano-copper catalysts, can solve the problems of difficult recovery of metal catalysts, harm to human health, and large environmental pollution, and achieves low cost and easy method. Line, wide application effect

Active Publication Date: 2022-05-20
HUBEI ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above reaction is carried out in a homogeneous system, the metal catalyst is difficult to recover, and it is easy to cause metal residues in the drug synthesis, which seriously endangers human health, and the use of pure organic solvents causes greater environmental pollution.

Method used

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  • A kind of chitosan/polyvinyl alcohol composite membrane supported nano-copper catalyst and its application
  • A kind of chitosan/polyvinyl alcohol composite membrane supported nano-copper catalyst and its application
  • A kind of chitosan/polyvinyl alcohol composite membrane supported nano-copper catalyst and its application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The preparation method of compound II-1, its steps are:

[0039]

[0040] A. Add starting material I-1 to a 3mL reaction bottle: (0.2mmol), pinacol borate (B 2 (pin 2 )) (0.2mmol), CP@Cu (5mg), 4-methylaniline (3mmol%), magneton, deionized water (3mL), stirred at room temperature (20-25°C, the same below) for 12 hours.

[0041] B. After the reaction, filter the entire reaction system, transfer the filtrate to a separatory funnel and add 15 mL of saturated saline, extract with 15 mL of ethyl acetate, remove excess solvent from the obtained organic phase, and use column chromatography to control the mobile phase Separation in the ratio (ethyl acetate:petroleum ether=1:10), and purification by silica gel column chromatography to obtain 61.9 mg of boride II-1 with a yield of 92%.

[0042] 1 H NMR (400MHz, Chloroform-d); ,7.18–7.11(m,1H),4.85–4.69(m,1H),1.58(dd,J=15.9,9.2Hz,1H),1.34(dd,J=15.9,6.7Hz,1H),1.19(s ,6H),1.12(s,6H).

[0043] 13 C NMR (101MHz, Chloroform...

Embodiment 2

[0046] The preparation method of compound II-2, its steps are:

[0047]

[0048] A. Add starting material I-2 to a 3mL reaction bottle: (0.2mmol), pinacol borate (B 2 (pin 2 )) (0.2mmol), CP@Cu (5mg), 4-methylaniline (3mmol%), magneton, deionized water (3mL), stirred at room temperature (20-25°C, the same below) for 12 hours.

[0049] B. After the reaction, filter the entire reaction system, transfer the filtrate to a separatory funnel and add 15 mL of saturated saline, extract with 15 mL of ethyl acetate, remove excess solvent from the obtained organic phase, and use column chromatography to control the mobile phase Separation (ethyl acetate:petroleum ether=1:10), purified by silica gel column chromatography to obtain boride II-2 66.5mg, yield 95%.

[0050] 1 H NMR (400MHz, Chloroform-d); ,7.05(d,J=7.9Hz,2H),4.81–4.71(m,1H),2.25(s,3H),1.57(dd,J=15.9,9.5Hz,1H),1.30(dd,J=15.9 ,6.5Hz,1H),1.19(s,6H),1.13(s,6H).

[0051] 13 C NMR (101MHz, Chloroform-d);

Embodiment 3

[0053] The preparation method of compound II-3, its steps are:

[0054]

[0055] A. Add starting material I-3 to a 3mL reaction bottle: (0.2mmol), pinacol borate (B 2 (pin 2 )) (0.2mmol), CP@Cu (5mg), 4-methylaniline (3mmol%), magneton, deionized water (3mL), stirred at room temperature (20-25°C, the same below) for 12 hours.

[0056] B. After the reaction, filter the entire reaction system, transfer the filtrate to a separatory funnel and add 15 mL of saturated saline, extract with 15 mL of ethyl acetate, remove excess solvent from the obtained organic phase, and use column chromatography to control the mobile phase Separation (ethyl acetate:petroleum ether=1:10), purified by silica gel column chromatography to obtain boride II-3 75.4mg, yield 91%.

[0057] 1 H NMR (400MHz, Chloroform-d); 7.11(m,1H),7.08–6.98(m,2H),5.25–5.06(m,1H),1.40(dd,J=15.8,10.2Hz,1H),1.29(dd,J=15.8,5.6Hz, 1H), 1.22(s,6H), 1.16(s,6H).

[0058] 13 C NMR (101MHz, Chloroform-d);

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Abstract

The invention discloses a chitosan / polyvinyl alcohol composite film-loaded nano-copper catalyst and its application. The catalyst is applied to the preparation of an organoboron compound containing an α-substituted propionate structure, comprising the following steps: adding Chitosan / polyvinyl alcohol composite film supported nano-copper catalyst CP@Cu, solvent, substrate I, base, pinacol borate B 2 (pin) 2 , stirred and reacted at room temperature, and the reaction time was 6-24 hours. After the reaction, separation and purification were carried out to obtain the organoboron compound II containing the α-substituted propionate structure. The catalyst is low in consumption and recyclable, easy to separate after the reaction, no metal residue, mild reaction conditions, simple post-treatment, and suitable for large-scale production.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a chitosan / polyvinyl alcohol composite membrane-loaded nano-copper catalyst and an application thereof. Background technique [0002] Molecules containing α-substituted propylene ester structures are widely present in drug molecules, and significant progress has been made in reducing blood pressure and anti-virus. However, the synthesis methods of such molecules are cumbersome and costly, which limits their further application in actual production. In recent years, literature (Angew.Chem.Int.Ed.2017,56,13314–13318) reported the synthesis of three-component compounds containing α-substituted propylene esters using Cu-catalyzed alkenes, aryl compounds, and biboronic acid pinacol esters. Structured borides, or participate in the reaction with CO, catalyzed by copper and palladium (Angew. Chem. Int. Ed. 2020, 59, 17055–17061), further realize the conversion of carbon-boron bonds. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/28B01J37/16C07F5/02C07C67/31C07C69/732C08L5/08C08L29/04C08J5/18
CPCB01J31/28B01J37/16C07F5/025C07C67/31C08J5/18B01J2231/323C08J2305/08C08J2429/04B01J35/23B01J35/59C07C69/732Y02P20/584
Inventor 朱磊韩彪文蔚张瑶瑶李博解夏彩芬颜永斌李伟汪连生
Owner HUBEI ENG UNIV