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(R)-CuTAPBP-COF polymer as well as preparation method and application thereof

A polymer, -BIONLPA-DA technology, applied in the direction of organic chemical methods, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problem that homogeneous catalysts are difficult to separate, difficult to recycle, etc. problem, to achieve high yield and stereoselectivity, easy recovery, and cost reduction

Active Publication Date: 2021-08-03
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, homogeneous catalysis is the mainstream of asymmetric catalytic synthesis of (R)-2-methyl-3-(pyridin-4-yl)propanal, but homogeneous catalysts have problems such as difficult separation and difficult recycling. Under the circumstances, the heterogeneous chiral catalyst has the advantages of reusability, meets the requirements of sustainable development, and shows broad development prospects. Therefore, it provides an effective catalytic synthesis of (R)-2-methyl-3-(pyridine Heterogeneous chiral catalysts of -4-yl)propionaldehyde are of great significance

Method used

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  • (R)-CuTAPBP-COF polymer as well as preparation method and application thereof
  • (R)-CuTAPBP-COF polymer as well as preparation method and application thereof
  • (R)-CuTAPBP-COF polymer as well as preparation method and application thereof

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Experimental program
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preparation example Construction

[0051]Further, the preparation method includes reacting Cu-TAPP and (R) -BionLPa-DA to the mixed solution of ethanol, average toluene and dilute acetic acid, i.e., the polymer (r) -CutApbp-COF.

[0052] Preferably, the reaction temperature is 110-120 ° C.

[0053] Preferably, the reaction time is 3-3.5d.

[0054] Preferably, the molar ratio of Cu-TAPP and (R) -BionLPa-Da is 1: 2.

[0055] Preferably, the volume ratio of the ethanol, average toluene and dilute acetic acid is 17: 3: 2.

[0056] Further preferred, the preparation method also includes: After the reaction, the solid portion is collected by ethanol, which is obtained by ethanol, i.e., the polymer (R) -CutApBP-COF.

[0057] In one or more embodiments of the invention, the synthesis method of the (R) -bionlpa-DA is:

[0058] Under nitrogen, weigh the amount of (R) -BionLDH-DA, add anhydrous pyridine, and then dropped to the reaction system plus POCl. 3 , Mixed, resulting in (r) -bionlpa-da.

[0059] Further, (R) -BionLDH-...

Embodiment 1

[0092] Example 1: (r) Synthesis of -BionLPa-DA

[0093] (R) -1, 1'-joint-2-naphthol (10.0 mmol, 2.86 g) was placed in a 100 ml of three flasks, dichloromethane (20 mL), cooled to 0 ° C, slowly dropped under stirring. Liquid bride (25.2 mmol, 4.00 g), reacted at 0 ° C for 24 h, add NA 2 S 2 O 3 (7.4 mmol, 1.20 g) of aqueous solution was quenched, and stirring was continued for 2 h. After the reaction is completed, the reaction liquid becomes pale yellow by orange. The reaction solution was filtered to the liquid filter into the separatory funnel, and the organic phase was washed three times with a saturated NaCl solution, and the organic phase was stirred and evaporated in vacuo to give a light yellow solid (R) -db.

[0094] Weigh (R) -DB (10.0 mmol, 4.44g), no water K 2 CO 3 (40.0 mmol, 5.50 g), bromoethane (60.0 mmol, 7.00 g) was placed in a 100 mL of two flasks, and acetone (40 ml) was added, and the heat was refluxed for 48 h. After the reaction was completed, cooled to room te...

Embodiment 2

[0100] Example 2: (r) Synthesis of -Cutapbp-Cof

[0101] Cu-TAPP (0.05 mmol, 36.60 mg), (r) -bionlPa-DA (0.1 mmol, 61.60 mg) was placed in a 10 ml pressure resistant tube, adding acetic acid (9M, 0.2 mL), ethanol / average toluene ( 5: 1, 2 mL) Mixed solvent, ultrasonic 10min makes mixing uniform. The liquid nitrogen was frozen three times, and then heated at 120 ° C for 72 h. After the reaction was completed, then cooled to room temperature, and left 48 h. The solid was centrifuged, washed with ethanol, and the purple black product (R) -CutApbp-Cof was obtained with ethanol.

[0102] This embodiment is passed by scanning electron microscopy, thermal weight, PXRD, solid nuclear magnetic, N 2 Adsorption characterized the compound, the results were respectively figure 1 , 2 , 3, 4 and 5, by figure 1 and Figure 5 The polymer can be confirmed that the polymer has a pore structure, the heat weight of the catalyst (R) -CutApbp-COF ( figure 2 ), PXRD ( image 3 ), Solid nuclear magnetic (...

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Abstract

The invention belongs to the technical field of COF catalysts, and particularly relates to a (R)-CuTAPBP-COF polymer as well as a preparation method and application thereof. The polymer (R)-CuTAPBP-COF provided by the invention has a good photothermal conversion property; and as the (R)-CuTAPBP-COF is used as a catalyst, the reaction of propionaldehyde with 4-(bromomethyl)pyridine can be effectively catalyzed through photothermal conversion to obtain an angiogenesis inhibitor intermediate, namely (R)-2-methyl-3-(pyridin-4-yl)propionaldehyde, the yield and stereoselectivity of the catalytic reaction are very high, heterogeneous catalysis is realized, the catalyst can be repeatedly utilized five times or more, the catalyst is easy to recycle, the utilization rate of the catalyst is improved, and cost is reduced.

Description

Technical field [0001] The present invention belongs to the technical field of COF catalysts, and more particularly to a (r) -CutApbp-COF polymer and method thereof and its preparation method thereof. Background technique [0002] The information disclosed in the background is only intended to increase the understanding of the overall background of the present invention, and is not necessarily considered to recognize or imply that the information is intended to be a prior art known to those of ordinary skill in the art. [0003] The chiral is the basic characteristics of nature. Most of the important biomolecules that participate in life activities such as nucleic acids, proteins and sugars are all chiral. In recent years, people's demand for sexual compounds such as chiral medicine and chiral pesticides have grown, which greatly promotes the development of asymmetric synthesis. At present, the unsociabled catalytic synthesis has achieved huge progress, thousands of chiral ligand...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G12/26B01J31/22C07D213/48
CPCC08G12/26B01J31/183C07D213/48C07B2200/07B01J2231/4205Y02P20/584
Inventor 董育斌马慧超陈功军
Owner SHANDONG NORMAL UNIV
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