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A kind of (r)-tapp-binol-cof polymer, its preparation method and application

A -TAPP-BINOL-COF, -BINOL-CHO technology, applied in the field of COF catalysts, can solve the problems of increased production cost of clopidogrel, three wastes, low yield, poor chiral selection, etc. Highly selective, inexpensive, and easy to separate effects

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

AI Technical Summary

Problems solved by technology

There are many synthetic routes about clopidogrel reported at present, but the existing clopidogrel preparation technology generally has poor chiral selection, needs repeated chiral resolution, and problems such as low yield, which make the production of clopidogrel Increase in cost and waste

Method used

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  • A kind of (r)-tapp-binol-cof polymer, its preparation method and application
  • A kind of (r)-tapp-binol-cof polymer, its preparation method and application
  • A kind of (r)-tapp-binol-cof polymer, its preparation method and application

Examples

Experimental program
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Effect test

preparation example Construction

[0051] Preferably, the preparation method includes: adding Cu-TAPP and (R)-BINOL-CHO to a mixed solution of dilute acetic acid, mesitylene and 1,4-dioxane for reaction.

[0052] Preferably, the reaction temperature is 110-130°C.

[0053] Preferably, the reaction time is 2.5-3.5d.

[0054] Preferably, the molar mass ratio of Cu-TAPP to (R)-BINOL-CHO is 0.8-1.2:1.8-2.2.

[0055] Preferably, the volume ratio of the dilute acetic acid, mesitylene and 1,4-dioxane is 2-4:4-6:14-17.

[0056] Preferably, the preparation method further includes: after the reaction is completed, collecting the solid part and washing with ethanol to obtain a purple-black powder, that is, the polymer (R)-TAPP-BINOL-COF.

[0057] The third aspect of the present disclosure provides the use of the polymer described in the first aspect as a catalyst.

[0058] Preferably, the catalyst is a clopidogrel intermediate catalyst; further, as (S)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c ]pyridin-5 (4H)-yl) a...

Embodiment 1

[0067] Embodiment 1: the synthesis of (R)-BINOL-CHO

[0068] Put R-1,1'-bi-2-naphthol (10.0mmol, 2.86g) in a 100ml three-necked flask, add dichloromethane (20ml), cool to 0°C, and slowly add liquid bromine ( 25.2mmol, 4.00g), after the dropwise addition was completed, the reaction solution was light orange. After continuing the reaction at 0°C for 24 h, add Na 2 S 2 o 3 (7.4mmol, 1.20g) aqueous solution, continue to stir for 2h. After the reaction was completed, the color of the reaction solution changed from orange to light yellow. Filter the reaction solution, transfer the filtrate to a separatory funnel, wash the organic phase three times with saturated NaCl solution, combine the organic phases, and add an appropriate amount of NaCl 2 SO 4 After drying, the solvent was removed by rotary evaporation to obtain (R)-6,6'-dibromo-1,1'-bi-2-naphthol as a light yellow solid product.

[0069] Weigh (R)-6,6'-dibromo-1,1'-bi-2-naphthol (10.0mmol, 4.44g) into a 100ml flask, add...

Embodiment 2

[0073] Example 2: Synthesis of (R)-TAPP-BINOL-COF

[0074] Cu-TAPP (0.05mmol, 36.60mg), (R)-BINOL-CHO (0.10mmol, 61.60mg), dilute acetic acid (6M, 0.30ml) and 1,4-dioxane / mesitylene (2ml , volume ratio = 3:1) solution into the pressure tube. Freeze with liquid nitrogen, vacuumize, and then thaw. The above operation is repeated three times, and then placed in a constant temperature oven at 120°C for 3 days. After cooling to room temperature, it was collected by centrifugation, washed repeatedly with ethanol, and vacuum-dried to obtain a purple-black Cu-COF powder with a yield of 82%.

[0075] In this embodiment, solid NMR, PXRD, N 2 The compound was characterized by adsorption and TGA, and the results are shown in figure 1 , 5 , 6 and 7. It can be seen that the polymer has a hollow structure. The ultraviolet absorption of (R)-TAPP-BINOL-COF prepared by the above method in acetonitrile solution ( image 3 ) shows that it has the maximum absorption at 420nm, and find the t...

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Abstract

The disclosure belongs to the technical field of COF catalysts, and specifically relates to a (R)-TAPP-BINOL-COF polymer, its preparation method and application. The present disclosure provides a preparation method and application of a covalent organic framework (R)-TAPP-BINOL-COF, wherein the (R)-TAPP-BINOL-COF is crystallized in the C2 space group. The catalyst can effectively catalyze the synthesis reaction of a clopidogrel intermediate through photothermal conversion under light conditions, the reaction conditions are mild, the reaction time is short, the amount of catalyst is small, it can be reused more than five times, and it is used in industrial production makes good economic sense.

Description

technical field [0001] The disclosure belongs to the technical field of COF catalysts, and in particular relates to a two-dimensional chiral (R)-TAPP-BINOL-COF polymer, its preparation method, and its application as a chiral drug clopidogrel precursor catalyst. Background technique [0002] The information disclosed in this Background section is only intended to increase the understanding of the general background of the disclosure, and is not necessarily to be taken as an acknowledgment or any form of suggestion that the information constitutes prior art that is already known to those skilled in the art. [0003] Covalent organic frameworks (COFs) are a class of crystalline porous materials, which consist of organic building units connected by covalent bonds into an ordered structure, forming a periodic porous COFs framework. COFs have the advantages of large specific surface area, light weight, and stable structure, and have good development prospects in the fields of cata...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/00B01J31/22C07D495/04
CPCC08G73/00B01J31/1691B01J31/183C07D495/04B01J2531/025B01J2531/16C07B2200/07
Inventor 董育斌马慧超陈功军
Owner SHANDONG NORMAL UNIV
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