Terphenyl macrocyclic compound based on biphenyl aromatic hydrocarbon and preparation method of terphenyl macrocyclic compound

A technology of macrocyclic compounds and biphenyl aromatic hydrocarbons, applied in the field of supramolecular macrocycles and their synthesis and preparation, can solve the problems of low yield of macrocyclic compounds, insufficient number of alkoxy groups, complex reactions, etc., and achieve low cost, The effect of high reaction efficiency and simple synthesis method

Pending Publication Date: 2021-05-14
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing general cyclization reaction to prepare macrocyclic compounds still has shortcomings such as low yield, insufficient number of alkoxy groups, complicated reaction and high cost, which have become technical problems to be solved urgently.

Method used

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  • Terphenyl macrocyclic compound based on biphenyl aromatic hydrocarbon and preparation method of terphenyl macrocyclic compound
  • Terphenyl macrocyclic compound based on biphenyl aromatic hydrocarbon and preparation method of terphenyl macrocyclic compound
  • Terphenyl macrocyclic compound based on biphenyl aromatic hydrocarbon and preparation method of terphenyl macrocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] In this embodiment, a synthetic method of 2,2',4,4',6,6'--hexamethoxyterphenyl, the steps are as follows:

[0053] (1-1) In a 100ml round bottom flask, 1g of 1,4-dibromobenzene (CAS: 106-37-6) was completely dissolved in 30mL of 1,4-dioxane aqueous solution to obtain 1, 4-dibromobenzene mixed solution; the mass ratio of 1,4-dioxane and water in the 1,4-dioxane aqueous solution is 5:1;

[0054] (1-2) Then add 1.4g of 2,4,6-trimethoxyphenylboronic acid (CAS: 135159-25-0) and 0.4g of tetrakistriphenylphosphine palladium to the 1,4-dibromobenzene mixture , 4.2g sodium carbonate, obtain mixed liquid system;

[0055] (1-3) Then, the mixed liquid system was heated to 100° C. and refluxed overnight for reaction;

[0056] (1-4) When the reaction is over, cool the reaction solution to room temperature, spin the solvent to dry, dissolve in dichloromethane, extract with water three times, and wash the organic layer with anhydrous Na 2 SO 4 Dried, and spin-dried again to mix the...

Embodiment 2

[0060] This embodiment is basically the same as Embodiment 1, especially in that:

[0061] In this example, a synthetic method of 2,2',3,3'-tetramethoxyterphenyl, the steps are as follows:

[0062] (1-1) In a 100ml round bottom flask, 1g of 1,4-dibromobenzene (CAS: 106-37-6) was completely dissolved in 30mL of 1,4-dioxane aqueous solution to obtain 1, 4-dibromobenzene mixed solution; the mass ratio of 1,4-dioxane and water in the 1,4-dioxane aqueous solution is 5:1;

[0063] (1-2) Then add 1.2 g of 2,3-dimethoxyphenylboronic acid (CAS: 40972-86-9), 0.4 g of tetrakistriphenylphosphine palladium to the 1,4-dibromobenzene mixture, 4.2g sodium carbonate, obtain mixed liquid system;

[0064] (1-3) Then, the mixed liquid system was heated to 100° C. and refluxed overnight for reaction;

[0065] (1-4) When the reaction is over, cool the reaction solution to room temperature, spin the solvent to dry, dissolve in dichloromethane, extract with water three times, and wash the organic ...

Embodiment 3

[0069] This embodiment is basically the same as the previous embodiment, and the special features are:

[0070] In this example, a method for preparing a 2,2',4,4',6,6'-hexamethoxyterphenyl aromatic hydrocarbon macrocyclic compound, the steps are as follows:

[0071] (2-1) Add 0.1g monomer 2,2',4,4',6,6'-hexamethoxyterphenyl and 0.05g paraformaldehyde into a 100mL round bottom flask to obtain a mixed solution;

[0072] (2-2) Pour 60 mL of 1,2-dichloroethane into the mixed solution as a solvent, add 0.1 mL of boron trifluoride etherate complex while stirring, and monitor the reaction point;

[0073] (2-3) After 30 minutes of reaction, add 30 mL of saturated sodium bicarbonate solution to quench the reaction; then pour the reaction solution into a separatory funnel, wash with 50 mL of saturated sodium chloride solution, and dry over anhydrous sodium sulfate. The resulting mixture was separated with a silica gel column to obtain 60 mg of a white solid 2,2',4,4',6,6'-hexamethoxyt...

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Abstract

The invention discloses a terphenyl macrocyclic compound based on biphenyl aromatic hydrocarbon and a preparation method of the terphenyl macrocyclic compound. The preparation method comprises the steps: firstly, preparing 2,2', 4,4',6,6'-hexamethoxy terphenyl or 2,2',3,3'-tetramethoxy terphenyl as a monomer through suzuki coupling reaction, then adding paraformaldehyde and 1,2-dichloroethane into the monomer, and under the catalysis of lewis acid boron trifluoride diethyl etherate, obtaining 2,2',4,4',6,6'-hexamethoxy terphenyl arene macrocycles and 2,2',3,3'-tetramethoxy terphenyl arene macrocycles with high yield by a one-pot method. The raw materials are easy to obtain, the reaction is efficient, the one-pot synthesis is simple and convenient, the yield is high, and more methoxy side chains are provided for further modification. The similar macrocycles show great scientific research value in the field of adsorption separation materials, so that there are reasons to believe that the method has a wide application prospect in the fields of materials, environment, biology and the like.

Description

technical field [0001] The invention relates to a supramolecular macrocycle and its synthesis and preparation method, in particular to a synthesis and preparation method of a terphenyl macrocycle compound, which is applied to the technical field of macrocycle compounds and their preparation technology. Background technique [0002] Since the discovery of the first generation of macrocyclic hosts, it has been proven that macrocycles are essential for molecular recognition and assembly and thus have enormous applications in chemistry, materials and biology. Their widespread use makes the creation of new macrocycles an attractive target. Much effort has been devoted to the synthesis of macrocycles such as "Texas-sized" boxes, ExBox, pillararene, bambus[6]uril, columnar complexes, cycloparaphenylene, caliximidazole, calixyrrole, etc. Furthermore, for most macrocycles, tedious synthesis and rather low yields have been a great obstacle for their further development. 2,2-diethoxy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/21C07C41/30
CPCC07C43/21C07C2603/92
Inventor 徐凯迪李春举崔雷
Owner SHANGHAI UNIV
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