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Aryl beta-amino ketone compound and preparation method thereof

A compound, the technology of aminoketone, applied in the field of aryl β-aminoketone compound and its preparation, can solve the problems that various affinity reagents cannot be used, and achieve the effect of cheap market price, easy promotion and application, and low raw material cost

Active Publication Date: 2019-07-12
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] A variety of affinity reagents cannot be applied to this method, which makes this method have great limitations

Method used

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  • Aryl beta-amino ketone compound and preparation method thereof
  • Aryl beta-amino ketone compound and preparation method thereof
  • Aryl beta-amino ketone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] A kind of preparation method of aryl β-amino ketone compound comprises the steps:

[0045] S1: Under atmospheric atmosphere, mix 0.2mmol 1-(2,2-dimethylcyclopropyl) 4-methoxybenzene, 0.4mmol pyrazole, 100mg4A molecular sieve, 0.0004mmol [Ir(dF(CF 3 )ppy) 2 (5,5'-bpy)](PF 6 ) was sequentially added to 1.0mL 1,2-dichloroethane to obtain a mixture;

[0046] S2: Substituting oxygen, under an oxygen atmosphere, irradiate the mixture obtained in step S1 under blue light with a wavelength of 450nm and an intensity of 8W LED for 16 hours, and then collect aryl β-amino ketone compound 1 from the reaction product .

Embodiment 2

[0048] A kind of preparation method of aryl β-amino ketone compound comprises the steps:

[0049] S1: Add 0.22mmol 1-dodecene, 0.2mmol (4-methoxyphenyl)(tri-n-butyltin-based) methyl carbonate to 1.0mL 1,2-dichloroethane under argon atmosphere , after cooling to -23°C, add 0.2mmol boron trifluoride diethyl ether dropwise, then stir the reaction solution at -23°C for 2 hours, then warm the reaction solution to room temperature, add 0.4mmol pyrazole, 100mg 4A molecular sieve, 0.0004mmol of [Ir(dF(CF 3 )ppy) 2 (5,5'-bpy)](PF 6 ), to obtain a mixture;

[0050] S2: replace oxygen, under an oxygen atmosphere, irradiate the mixture obtained in step S1 under blue light with a wavelength of 450nm and an intensity of 8W LED for 16 hours, and then collect aryl β-amino ketone compound 2 from the reaction product .

Embodiment 3～58

[0052] The numbering of the aryl cyclopropane, ammonia source and synthetic compound adopted in the embodiments 3~58 is shown in Table 1, and their preparation method is the same as embodiment 1:

[0053] Relevant information of table 1 embodiment 3~58

[0054]

[0055]

[0056]

[0057]

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Abstract

The invention discloses an aryl beta-amino ketone compound and a preparation method thereof, and belongs to the technical field of organic chemical synthesis. The preparation method comprises the steps that aryl cyclopropane, an ammonia source, a drying agent and a photocatalyst are sequentially added in a solvent at an atmospheric atmosphere to obtain a mixture; then the obtained mixture reacts under an illumination condition at an oxygen atmosphere; finally, the aryl beta-amino ketone compound is collected from the reaction product. According to the method, electron-rich aryl cyclopropane serves as a raw material, aryl groups become free radical positive ions through single-electron oxidation, and the nucleophilic attack process of an amino nucleophilic reagent is promoted; the product is obtained by making the free radical positive ions react with oxygen through benzyl radical generation, the raw materials are simple and easy to obtain, and the cost is relatively low; tedious pre-functionalization steps are avoided; the preparation method takes light as an energy source and can achieve the reaction at room temperature; the reaction conditions are mild and environmentally friendly.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to an aryl β-amino ketone compound and a preparation method thereof. Background technique [0002] Cyclopropane compounds are important organic structural monomers, which widely exist in natural products and various pharmaceutically active molecular structures. Due to the inherent characteristics of the cyclopropane structure and its large ring tension, it can realize the ring-opening effect through a variety of ways, which also makes the cyclopropane compound an important unit in modern organic synthesis. Remarkably, by exploiting thermodynamic ring strain release, we can obtain products of selective carbon-carbon bond scission. [0003] Currently, there are four main strategies for cleaving three-membered or four-membered rings via carbon-carbon bond cleavage. [0004] One, such as literature 1 (Chakrabarty, S.; Chatterjee, I.; Wibbeling, B.; Daniliuc, C.G.; S...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/12C07D405/06C07D231/16C07D249/08C07D249/04C07D249/18
CPCC07D231/12C07D405/06C07D231/16C07D249/08C07D249/04C07D249/18Y02P20/584
Inventor 冯超葛亮
Owner NANJING TECH UNIV