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Method for preparing anthracycline dimer through photocatalysis

An anthracycline dimer, photocatalytic technology, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc. The effect of widening reaction conditions and good application prospects

Active Publication Date: 2020-08-25
SHANDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] On the other hand, there are other side reactions during the photodimerization reaction of anthracycline molecules. The substrate molecules or free radicals in the excited state can react with oxygen in the system to obtain unwanted by-products, which greatly reduces the conversion rate of the reaction

Method used

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  • Method for preparing anthracycline dimer through photocatalysis
  • Method for preparing anthracycline dimer through photocatalysis
  • Method for preparing anthracycline dimer through photocatalysis

Examples

Experimental program
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Embodiment 1

[0028] Add 9-anthracene formaldehyde (0.010 g, 0.05 mmol), cage compound Ni-L1 (1mol%) and tetrabutylammonium bromide TBABr (5 mol%) in a 25 mL test tube reactor, add mixed deuterium reagent CDCl 3 and DMSO- d 6 , the volume ratio is 1:6, under the atmosphere of air, after irradiating with 500 W xenon lamp for 8 hours, directly absorb the solution to detect the yield of its dimerization product by NMR, and analyze and detect the by-product by GC-MS, the final yield is 94 %, the selectivity is 92%.

Embodiment 2

[0030] Add 9-anthracenecarboxylic acid (0.011 g, 0.05 mmol), cage compound Ni-L1 (1mol%) and tetrabutylammonium bromide TBABr (5 mol%) in a 25 mL test tube reactor, add mixed deuterated reagent CDCl 3 and DMSO- d 6 , the volume ratio is 1:6, under the atmosphere of air, after irradiating with 500 W xenon lamp for 4 hours, directly absorb the solution to detect the yield of dimerization products by NMR, and use GC-MS to analyze and detect the by-products, the final yield is 96 %, the selectivity is 95%.

Embodiment 3

[0032] Add methyl 9-anthracenecarboxylate (0.012 g, 0.05 mmol), cage compound Ni-L1 (1 mol%) and tetrabutylammonium bromide TBABr (5 mol%) in a 25 mL test tube reactor, add mixed deuterium Reagent CDCl 3 and DMSO- d 6 , the volume ratio is 1:6, in the atmosphere of air, after irradiating with a 500 W xenon lamp for 8 hours, directly draw the solution for nuclear magnetic detection to detect the yield of dimerization products, and use GC-MS to analyze and detect by-products, the final yield is 100 %, the selectivity is 100%.

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Abstract

The invention relates to the technical field of supramolecular catalysis. The invention discloses a method for preparing an anthracycline dimer through photocatalysis. An anthracycline derivative is used as a reaction substrate, a metal-organic cage compound is used as a catalyst, a reaction cavity is provided, the anthracycline derivative can be converted into a corresponding anthracycline dimerwith high selectivity in an air atmosphere through irradiation of a light source under the participation of a cocatalyst, generation of reaction byproducts is avoided, reaction conditions can be widened, and mild synthesis in the air atmosphere is realized. In addition, by selecting a metal center, active Ni<2+> is introduced into the system, and the efficiency of the photodimerization reaction can be actively promoted. Compared with the prior art, the method provided by the invention has the characteristics of mild reaction conditions, convenient detection, high specific selectivity, no generation of by-products and the like, and has very good application prospects in the fields of photocatalytic dimerization reaction systems and the like.

Description

technical field [0001] The invention relates to a method for preparing anthracycline dimer by photocatalysis, belonging to the field of supramolecular catalysis. Background technique [0002] Photodimerization is an important reaction in photoreaction chemistry. Under the action of light, two identical or different organic molecules polymerize to form their corresponding dimers, which mostly occur between photoactive olefin molecules or aromatic molecules to form a ring. Polymerization reaction can be used as a kind of method to directly form C-C bonds effectively, and it can show the advantages of being greener, simpler and energy-saving than other types of organic reactions. According to the number of ring atoms, the photodimerization reaction can be divided into [2+2], [4+4], [4+2] and other types. From the perspective of the reaction process, the reaction substrate molecule needs to be photoactivated to its excited state, or generate free radicals under photoexcitation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/53C07F9/50
CPCC07D213/53C07F9/5022Y02P20/584
Inventor 杨璐秦兰周振潘玉张家乐徐梦真
Owner SHANDONG UNIV OF TECH
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