Preparation method and application of metal-organic framework structure compound with chiral pore channel structure

A technology of pore structure and organic framework, applied in the direction of indium organic compounds, platinum group organic compounds, organic compounds/hydrides/coordination complex catalysts, etc. Good recycling, high price and other issues, to achieve the effect of chiral cavity photocatalytic properties, excellent photocatalytic properties, and low price

Inactive Publication Date: 2020-05-08
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The chiral auxiliary ligand synthesis process is complex and expensive
In the photocatalytic asymmetric synthesis system, the participation of chiral auxiliary ligands is not avoided, and all noble metal catalysts cannot be recycled well, which greatly increases the cost of asymmetric catalysis, and causes pollution and waste

Method used

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  • Preparation method and application of metal-organic framework structure compound with chiral pore channel structure
  • Preparation method and application of metal-organic framework structure compound with chiral pore channel structure
  • Preparation method and application of metal-organic framework structure compound with chiral pore channel structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 4-Bromophenylboronic acid (2.4g, 12mmol), potassium carbonate (3.32g, 24mmol) and palladium acetate (36mg, 0.16mmol) were added to 40mL of a mixed solvent of ethanol and water with a volume ratio of 3:1, and then 2 -Bromopyridine (790uL, 8mmol), react at 80°C for 2h. Cooled to room temperature, extracted with ethyl acetate and saturated brine, dried over anhydrous sodium sulfate, filtered and rotary evaporated, and passed through a silica gel column with a mixed solution of petroleum ether and ethyl acetate at a volume ratio of 100:1 to obtain 1.6 g of a white powder. Yield 86%. Add iridium trichloride (762.7mg, 2.54mmol) and white powder (1.5g, 6.44mmol) to 30mL of a mixed solvent of ethylene glycol monomethyl ether and water at a volume ratio of 3:1, and at 120°C Stir under reflux for 24h, after the reaction is completed, suction filter and wash the filter cake obtained by suction filtration with a small amount of water, ethanol and ether, and vacuum dry the filter c...

Embodiment 2

[0044] The right-handed helical chiral metal-based ligand Ir(III) complex L 1 (24mg, 0.025mmol) and tetraacetonitrile copper tetrafluoroborate (15.7mg, 0.05mmol) were added to 10mL of acetonitrile solvent, stirred at room temperature for 4h, after filtration, the filtrate was left at room temperature for 2 weeks, and green Solid, the target compound Cu-L was obtained 1 20 mg, yield 40%.

Embodiment 3

[0046] The right-handed helical chiral metal-based ligand Ir(III) complex L 1 (24mg, 0.025mmol) and tetraacetonitrile copper hexafluorophosphate (18.6mg, 0.05mmol) were added to 10mL of acetonitrile solvent, stirred at room temperature for 4h, after filtration, the filtrate was left at room temperature for 2 weeks, and green Solid, the target compound Cu-L was obtained 1 19 mg, yield 38%.

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Abstract

The invention belongs to the technical field of fine chemical engineering. The invention discloses a preparation method and application of a metal-organic framework structure compound with a chiral pore channel structure. In the preparation method, a right-handed spiral chiral metal-based ligand Ir (III) complex L1 or a left-handed spiral chiral metal-based ligand Ir (III) complex L2 is used as abasic construction module; Cu<+> with tetrahedral coordination configuration in a transition metal salt is used as a metal node, and the metal-organic framework structure compound with the chiral porechannel structure is prepared through reaction. The metal-organic framework structure compound having the chiral pore channel structure and prepared by the method is low in raw material price, high in yield and easy to put into practical application. The metal-organic framework structure compound is used as a compound Cu-L1 or Cu-L2 applied to catalysis of asymmetric oxidative dehydrogenation coupling (CDC) reaction of N-phenyl tetrahydroisoquinoline and phenylacetylene molecules, the highest yield can reach 80%, and the enantioselectivity is greater than 50%.

Description

[0001] The invention relates to a preparation method and application of a metal-organic framework compound with a chiral pore structure, belonging to the technical field of fine chemicals. Background technique [0002] Among the chemical drugs commonly used in the world today, chiral drugs account for more than 60%. The strict chiral matching and molecular recognition between different isomers of chiral drug molecules and macromolecules of living organisms will cause pharmacological activity and metabolic processes. Significant differences in terms of toxicity and so on. In terms of clinical treatment, taking enantiomerically pure chiral drugs can not only eliminate the toxic and side effects caused by invalid / unfavorable enantiomers, but also reduce the dosage and the metabolic burden of the human body on ineffective enantiomers, which has a significant impact on pharmacokinetics. And the dosage has better control, improves the specificity of the drug. Therefore, chiral chem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00B01J31/22C07F19/00C07D217/22
CPCB01J31/1815B01J35/004B01J2231/76B01J2531/827C07D217/22C07F15/0033
Inventor 段春迎肖兵何成李学召
Owner DALIAN UNIV OF TECH
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