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Synthetic method and antibacterial application of dialkylhydrogenated noppylbenzyl quaternary ammonium salt

A technology of dialkylhydrogenated noppylbenzyl and alkylhydrogenated noppylbenzyl, which is applied in the field of chemical synthesis of natural products, and achieves the effects of simple reaction operation, good inhibition effect and mild reaction conditions

Active Publication Date: 2018-03-20
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0006] At present, there are no reports on the synthesis methods of the seven dialkylhydrogenated noppylbenzyl quaternary ammonium salts and the antibacterial activity of their compounds against citrus pathogenic bacteria. Therefore, this patent explores the seven dialkylhydrogenated Synthetic method and antibacterial activity of nobyl benzyl quaternary ammonium salt, and a general synthetic method has been determined

Method used

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  • Synthetic method and antibacterial application of dialkylhydrogenated noppylbenzyl quaternary ammonium salt
  • Synthetic method and antibacterial application of dialkylhydrogenated noppylbenzyl quaternary ammonium salt
  • Synthetic method and antibacterial application of dialkylhydrogenated noppylbenzyl quaternary ammonium salt

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Experimental program
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Effect test

Embodiment 1

[0021] General Synthesis of Dialkyl Hydrogenated Noppylbenzyl Bromide (Chlorine)

[0022] Add about 0.02mol of dialkylhydrogenated nopylamine, 0.025mol of benzyl halide (bromine, chlorine) and appropriate amount of toluene into a 100mL Erlenmeyer flask equipped with a stirring bar and a condensing reflux device, and heat at 100-150°C 1-3d, take out the product, cool and crystallize, wash the obtained crystal with cold petroleum ether (60-90°C), filter with suction, wash with petroleum ether several times and then pump to dryness, then depressurize to remove possible residual solvent and dried to obtain the product.

Embodiment 2

[0024] The benzyl halide is benzyl chloride, the tertiary amine is N,N-dimethylhydrogenated noppylamine, and other experimental methods and conditions are the same as in Example 1 to obtain N,N-dimethyl-N-hydrogenated noppylamine Benzyl ammonium chloride.

[0025] MS (C 20 h 32 NCl): 356.4 (M + +Cl), 286.4 (M + -Cl), 677.3 (2M + +Cl), 607.4 (2M + -Cl),35(Cl);

[0026] 1 H NMR,δ H / ppm:7.686(2H,d,J=6.8Hz, 14- CH, 14’- CH),7.442(3H,t,J 1 =J 2 =6.8Hz, 15- CH, 15’- CH, 16- CH),5.084(2H,s, 12- CH),3.536(2H,m, 11- CH 2 ),2.311(1H,m, 2- CH),2.017~1.829(8H,m, 7- CH, 10- CH 2,3- CH, 5- CH, 1- CH, 4- CH 2 ),1.456(1H,m, 3- CH),1.196(3H,s, 9- CH 3 ),1.034(3H,s, 8- CH 3 ),0.825(1H,d,J=9.2Hz, 7- CH);

[0027] 13 C NMR,δ C / ppm:38.537(C -1 ), 46.113 (C -2 ), 22.089 (C -3 ),26.060(C -4 ), 41.040 (C -5 ), 38.537 (C -6 ), 30.182 (C -7 ), 23.313 (C -8 ), 27.923 (C -9 ), 33.360 (C -10 ), 67.242 (C -11 ), 62.797 (C -12 ), 127.497 (C -13 ), 133.211 (C ...

Embodiment 3

[0030] The benzyl halide is benzyl bromide, the tertiary amine is N,N-dimethylhydrogenated noppylamine, and other experimental methods and conditions are the same as in Example 1 to obtain N,N-dimethyl-N-hydrogenated noppylamine Benzyl ammonium bromide.

[0031] MS (C 20 h 32 NBr):446.2(M + +Br),286.4(M + -Br), 811.2 (2M + +Br),653.3(2M + -Br), 80.2(Br);

[0032] 1 H NMR,δ H / ppm:7.702(2H,d,J=6.8Hz, 14- CH, 14’- CH),7.441(3H,s, 15- CH, 15’- CH, 16- CH),5.098(2H,s, 12- CH 2 ),3.601(2H,m, 11- CH 2 ),3.296(6H,s,2 α- CH 3 ),2.305(1H,m, 2- CH),2.017~1.714(8H,m, 7- CH, 10 -CH 2,3- CH, 5- CH, 1- CH, 4- CH 2 ),1.470(1H,m, 3- CH),1.193(3H,s, 9- CH 3 ),1.034(3H,s, 8- CH 3 ),0.815(1H,d,J=9.2Hz, 7- CH);

[0033] 13 C NMR,δ C / ppm:38.501(C -1 ), 46.068 (C -2 ),22.100(C -3 ), 26.066 (C -4 ), 41.026 (C -5 ), 38.501 (C -6 ),30.166(C -7 ), 23.338 (C -8 ), 27.913 (C -9 ), 33.332 (C -10 ), 67.165 (C -11 ), 62.952 (C -12 ), 127.358 (C -13 ), 133.211 (...

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Abstract

The invention discloses a method for synthesizing dialkylhydrogenated noppylbenzyl quaternary ammonium salt compounds and the antibacterial application of such compounds. The invention is obtained by directly synthesizing dialkylhydrogenated noppylamine and benzyl halides in one step Dialkylhydrogenated noppyl benzyl quaternary ammonium salt, in an organic solvent, dialkylhydrogenated noppylamine and benzyl halide (chlorine, bromine, iodine) are fed into a stirring bar and equipped with a certain material ratio respectively Condensate in the Erlenmeyer flask of the reflux device, heat to react, the reaction temperature is controlled at 100-150°C, and the reaction time is controlled at 1-3d. After the reaction, the product is filtered, washed, recrystallized and vacuum-dried to obtain 7 kinds of dialkylhydrogenated notylbenzyl quaternary ammonium compounds respectively, and 7 kinds of dialkylhydrogenated notylbenzyl quaternary ammonium Both Phoma citri and Anthracnose citrus had good inhibitory effect. The invention has rich raw materials, simple operation, mild reaction conditions and simple post-purification treatment. Compared with traditional antibacterial agents, this type of antibacterial compound has the advantages of simple structure, safety and non-toxicity, less environmental pollution, etc., and has a good application prospect.

Description

technical field [0001] The invention belongs to the field of chemical synthesis of natural products, and in particular relates to a synthesis method of dialkylhydrogenated noppylbenzyl quaternary ammonium salt and the application of this type of compound in antibacterial aspects. technical background [0002] Quaternary ammonium salt is a kind of cationic surfactant, which has good antibacterial properties and good killing effect on microorganisms such as bacteria, fungi, algae and viruses. Widely concerned, the research on its biocidal mechanism and performance has always been a hot spot of research at home and abroad, and has made a lot of new progress. [0003] Antibacterial agent refers to a chemical preparation that kills or inhibits the biological activity of bacteria, fungi and other microorganisms within a certain period of time. Antimicrobial agents are widely used in agriculture, industry, and animal and plant protection. Quaternary ammonium salt antibacterial ag...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/12C07C211/63A01N33/12A01P3/00
CPCA01N33/12C07C209/12C07C211/63
Inventor 范国荣金霖霖肖转泉陈金珠王鹏陈尚钘王宗德廖圣良司红燕
Owner JIANGXI AGRICULTURAL UNIVERSITY
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