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Beta-nitroketone as well as preparation method and application method thereof

A technology for nitroketones and nitrohydrocarbons, applied in the field of organic chemical synthesis, which can solve the problems of difficult separation and purification and low yield of nitrohydrocarbons

Active Publication Date: 2022-03-22
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since nitrite is a zwitterion, nitrite ester products will be competitively formed in the substitution reaction, resulting in a low yield of nitrohydrocarbons, and separation and purification are very difficult

Method used

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  • Beta-nitroketone as well as preparation method and application method thereof
  • Beta-nitroketone as well as preparation method and application method thereof
  • Beta-nitroketone as well as preparation method and application method thereof

Examples

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preparation example Construction

[0022] This embodiment provides a method of preparation of β-nitrosyl ketone, including the following preparation step: as an enol silicone ether and a lazal nitro-hydrocarbon, under anhydrous solvent, a photoxidation reduction catalyst, at room temperature, The stirring reaction was stirred under visible light, and the reaction liquid was purified by purification of β-nitrone, and its reaction formula is as follows:

[0023]

[0024] In one example, in the above enol silica ether, R 1 R 2 The same or different groups can be selected independently. For example, R 1 From one of the following: C1 to C10 alkyl, C2 to C10 unsaturated hydrocarbon group, C3 to C10 of cycloalkyl, aryl; R 2 From one of the following: alkyl group of hydrogen, C1 to C8. Example floor, when R 2 When the alkyl group from C1 to C8, the alkyl group of C1 to C8 may include methyl, ethyl, n-propyl, isopropyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and the like. Rim 3 R 4 R 5 The alkyl group or phenyl groups ...

Embodiment 1

[0073] This example provides a method for preparing 3-methyl-3-nitro-1-phenyl-1-butanone, and the reaction formula is as follows:

[0074]

[0075] The preparation method includes the steps of: Take a completely dry Schlenk tube, vacuum nitrogen gas three times. 460 mg of 1-phenyl-1-trimethylsiloxyethylene (2.38 mmol), 200 mg of 2-bromo-2-nitropoxane (1.19 mmol) and 6.0 ml of anhydrous acetonitrile were added under nitrogen protection. 4mg FAC-IR (PPY) 3 (0.5 mol%). The reaction mixture was degassed by "frozen-vacuum-thaw" method, and then stirred under a 460 nm of 460 nm, 15W from the reaction tube, and the reaction temperature was controlled at 25 ° C, and the reaction was monitored by thin layer chromatography. After 2 hours, the reaction was completed. The concentrated reaction solution was rotationally evaporated to give a crude product. The crude product was purged with petroleum ether / ethyl acetate (volume ratio of 10: 1) rapid silica gel column chromatography to give a...

Embodiment 2

[0079] The reaction form is in the same embodiment. Visible photocatalyst FAC-IR (PPY) 3 The amount of amount was 8 mg (1.0 mol%), and the amount of other reagents was used as shown in Example 1.3-methyl-3-nitro-1-phenyl-1-butanone yield was 100%.

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PUM

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Abstract

The invention provides beta-nitroketone as well as a preparation method and an application method thereof. The preparation method comprises the following steps: by taking silyl enol ether and gem-halogenated nitrohydrocarbon as raw materials, in the presence of an anhydrous solvent, a photooxidation-reduction catalyst and illumination, carrying out a coupling reaction at room temperature under neutral conditions, and purifying and separating a reaction solution to obtain the beta-nitroketone. According to the preparation method disclosed by the invention, the adopted raw materials are cheap and easy to obtain, and the yield of more than 95% can be obtained. In addition, the prepared ketone with nitro located on beta-quaternary carbon can be easily converted into beta-aminoketone with important value.

Description

Technical field [0001] The present invention belongs to the field of organic chemical synthesis, and more particularly to β-nitricketate and its preparation method, application method. Background technique [0002] The β-amino ketone and 1,3-amino alcohol are a natural product and a structural unit that is generally present in the pharmaceutical compound. The carbonyl compound can be effectively bonded to the amine compound by Mannich reaction to form a β-amine group. The ketone is then converted to a very valuable 1,3-amino alcohol or β-amino acid. [0003] In the prior art, it is usually obtained by the mannich reaction to a ketone of N-modified amino groups, ie β-amine ketone. Β-nitrosyl ketone containing a primary amine or α-tertiary alkyl amine structure is difficult to prepare by the ManNich reaction. In practical applications, β-amine-based ketones prepared by the Mannich reaction often require all or part of the substituent on the N atom to introduce the required group. T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/45C07C201/12C07D309/08C07C205/54C07C315/04C07C317/24C07D307/46C07D333/22C07D213/50C07C225/16C07C221/00C07C213/00C07C215/30C07C253/30C07C255/56
CPCC07C205/45C07C201/12C07D309/08C07C205/54C07C315/04C07C317/24C07D307/46C07D333/22C07D213/50C07C221/00C07C213/00C07C253/30C07C255/56C07C2601/04C07C2601/08C07C2601/14C07C2601/18C07C2603/74C07C2601/02C07C2601/16C07C2602/10C07C225/16C07C215/30Y02P20/584
Inventor 焦鹏曹浩颖
Owner BEIJING NORMAL UNIVERSITY
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