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Preparation method of metallic organic macrocyclic crystalline-state material for splitting chiral amine

A metal-organic and chiral amine technology, which is applied in the field of preparation of metal-organic macrocyclic crystalline materials, can solve the problems of complex filling, expensive derivative-type chiral gas chromatography columns, cumbersome synthesis, etc., and achieve low reaction temperature, The effect of stable structure and simple synthesis operation

Inactive Publication Date: 2014-10-29
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the filling materials of chiral gas chromatographic columns used for the separation of chiral amines are mainly cyclodextrin derivatives. There are two shortcomings in the chiral gas chromatographic columns of cyclodextrin derivatives: one is the derivatization of cyclodextrin The synthesis of cyclodextrin is cumbersome, and the filling of cyclodextrin derivative chiral gas chromatographic column is more complicated; another disadvantage is that the price of cyclodextrin derivative chiral gas chromatographic column is relatively expensive
However, there are few reports on monochiral MOFs capable of separating chiral amines

Method used

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  • Preparation method of metallic organic macrocyclic crystalline-state material for splitting chiral amine
  • Preparation method of metallic organic macrocyclic crystalline-state material for splitting chiral amine
  • Preparation method of metallic organic macrocyclic crystalline-state material for splitting chiral amine

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Embodiment 1

[0033] A method for preparing a metal organic macrocyclic crystalline material for resolving chiral amines, the method first synthesizes a chiral ligand (1R, 2R)-H 2 L, the chiral ligand (1R, 2R)-H 2 L is R type, specifically (1R, 2R)-N-2-hydroxy-3-tert-butyl-5-(4-pyridine)benzylidene-N'-2-hydroxy-3-tert-butyl- 5-(4-pyridine) benzyl-cyclohexanediamine, and then prepare metal-organic macrocyclic crystalline materials for splitting chiral amines by solvothermal method, comprising the following steps:

[0034] (1) Chiral ligand (1R, 2R)-H 2 Preparation of L:

[0035]① Add 151mg (1R, 2R)-cyclohexanediamine unilateral hydrochloride into 20ml of anhydrous methanol, dissolve, and prepare a solution with a mass concentration of 7.55mg / ml, and then slowly dropwise add a mass concentration of 12.75mg / ml 20ml of 3-tert-butyl-2-hydroxy-5-(4-pyridine)benzaldehyde in anhydrous methanol solution, heated to reflux at 70°C for 6h, spin-dried, washed with anhydrous ether, filtered, and dried...

Embodiment 2

[0076] A method for preparing a metal organic macrocyclic crystalline material for resolving chiral amines, the method first synthesizes a chiral ligand (1R, 2R)-H 2 L, the chiral ligand (1R, 2R)-H 2 L is R type, specifically (1R, 2R)-N-2-hydroxy-3-tert-butyl-5-(4-pyridine)benzylidene-N'-2-hydroxy-3-tert-butyl- 5-(4-pyridine) benzyl-cyclohexanediamine, and then prepare metal-organic macrocyclic crystalline materials for splitting chiral amines by solvothermal method, comprising the following steps:

[0077] (1) Chiral ligand (1R, 2R)-H 2 Preparation of L:

[0078] ① Add (1R, 2R)-cyclohexanediamine unilateral hydrochloride into 20ml of anhydrous methanol, dissolve, and prepare a solution with a mass concentration of 7.2mg / ml, then slowly add 16ml of it with a mass concentration of 12.5mg / ml ml of 3-tert-butyl-2-hydroxy-5-(4-pyridine)benzaldehyde in anhydrous methanol solution, heated to reflux at 75°C for 7h, spin-dried, washed with anhydrous ether, filtered, and dried to ob...

Embodiment 3

[0084] A method for preparing a metal organic macrocyclic crystalline material for resolving chiral amines, the method first synthesizes a chiral ligand (1R, 2R)-H 2 L, the chiral ligand (1R, 2R)-H 2 L is R type, specifically (1R, 2R)-N-2-hydroxy-3-tert-butyl-5-(4-pyridine)benzylidene-N'-2-hydroxy-3-tert-butyl- 5-(4-pyridine) benzyl-cyclohexanediamine, and then prepare metal-organic macrocyclic crystalline materials for splitting chiral amines by solvothermal method, comprising the following steps:

[0085] (1) Chiral ligand (1R, 2R)-H 2 Preparation of L:

[0086] ① Add (1R, 2R)-cyclohexanediamine unilateral hydrochloride into 18ml of anhydrous methanol, dissolve, and prepare a solution with a mass concentration of 8.5mg / ml, and then slowly add 20ml of it with a mass concentration of 13.5mg / ml ml of 3-tert-butyl-2-hydroxy-5-(4-pyridine)benzaldehyde in anhydrous methanol solution, heated to reflux at 80°C for 8 hours, spin-dried, washed with anhydrous ether, filtered, and dr...

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Abstract

The invention relates to a preparation method of a metallic organic macrocyclic crystalline-state material for splitting chiral amine. The method firstly comprises the following steps: firstly synthesizing a chiral ligand (1R,2R)-H2L, wherein the chiral ligand (1R,2R)-H2L is (1R,2R)-N-2-hydroxyl-3-tertbutyl-5-(4-pyridine)benzylene-N'-2-hydroxyl-3-tertbutyl-5-(4-pyridine)benzyl-cyclohexanediamine; then preparing the metallic organic macrocyclic crystalline-state material for splitting chiral amine by adopting a solvothermal method. Compared with the prior art, by adopting the solvothermal method, the preparation method is low in reaction temperature, short in reaction time, low-cost in reaction raw materials, and easy to prepare, as well as simple for synthesis operations, without the need of complicated aftertreatment, the prepared chiral metallic organic macrocyclic crystalline-state material is very stable in structure, strong in selective adsorption capability, and high in splitting efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a method for preparing a metal-organic macrocyclic crystalline material used for splitting chiral amines. Background technique [0002] In recent years, chiral metal-organic materials have shown broad application prospects in the fields of chiral recognition and separation, chiral fluorescence sensing, and heterogeneous asymmetric catalysis due to their variable topological structures. One of the hot research fields such as chiral materials science. It has been shown that framework materials with amphiphilic pores may exhibit strong interactions with those amphiphilic guest molecules, as long as the pore size and morphology of MOFs match those of the guest molecules. Materials can perform chiral recognition and separation of some chiral molecules. At present, the filling materials of chiral gas chromatographic columns used for the separation of chiral amin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/53C07C209/88C07C211/07B01J20/22B01D15/38
CPCB01D15/3833B01J20/22C07C209/88C07D213/53C07C211/07
Inventor 崔勇董金桥周艳芳刘燕
Owner SHANGHAI JIAO TONG UNIV
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