Synthetic method of glycol mono-hydrogenated nopyl ether and carboxylic ester thereof and application thereof

A technology of monohydrogenated nopyl ether carboxylate and monohydrogenated nopyl ether, which is applied in the application field of antibacterial, and achieves the effects of mild conditions, high product yield and easy operation

Active Publication Date: 2018-05-29
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, still do not have the synthetic method of described ethylene glycol monohydrogenated nobyl ether and its carboxylic acid ester and the report of these compounds to plant pathogenic fungus antibacterial activity

Method used

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  • Synthetic method of glycol mono-hydrogenated nopyl ether and carboxylic ester thereof and application thereof
  • Synthetic method of glycol mono-hydrogenated nopyl ether and carboxylic ester thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Synthesis of ethylene glycol monohydronopyl ether: add 0.1mol hydronopyl bromide, 20g ethylene glycol, 30g 1,4-dioxane and 5.0g powdered sodium hydroxide in a 150mL conical flask, Put in a magnetic stirring bar, place it on the magnetic stirrer and install a reflux condenser, stir and heat to reflux. After 3 hours of reaction, the reaction solution was sampled for gas chromatographic analysis. If it is found that there is no more hydrogenated nobyl bromide in the reaction solution, stop heating, cool to room temperature, transfer the reaction solution to a separatory funnel, wash twice with saturated brine, dry over anhydrous sodium sulfate, and then recover by distillation Solvent, ethylene glycol monohydrogenated nopyl ether was distilled off under vacuum, b.p. 133~135℃ / 200 Pa, colorless liquid, yield 91%, GC purity 97.3%.

[0020] IR,ν max (cm -1 ): 1121(C-O-C).

[0021] 1 H NMR, δ H / ppm: 3.693(2H,t,J 1 =J 2 =4.6Hz, 13- CH 2 ),3.495(2H,t,J 1 =J 2 =4.6Hz,...

Embodiment 2

[0024] General method for the synthesis of ethylene glycol monohydrogenated nopyl ether carboxylate:

[0025] In a 100mL conical flask, add 0.03mol ethylene glycol monohydronopolyl ether, 0.06mol carboxylic acid, 25g water-carrying agent, 0.3g p-toluenesulfonic acid, magnetic stirring bar, install water separator and condenser, stir, Heating until the steam in the condenser tube is condensed, the reaction continues, and the turbidity no longer appears in the water separator for another 10 minutes, stop heating, cool, transfer the reaction solution to a separatory funnel, and sequentially use saturated sodium bicarbonate solution and saturated brine. Wash, dry with anhydrous sodium sulfate, recover the solvent by distillation, and evaporate the product by vacuum distillation.

Embodiment 3

[0027] The carboxylic acid is formic acid, the water-carrying agent is cyclohexane, and other experimental methods and conditions are the same as in Example 2, and ethylene glycol monohydrogenated nobyl ether formate is synthesized to obtain a colorless liquid, b.p.129~131℃ / 200Pa, obtain The yield was 94%, and the GC purity was 97.1%.

[0028] IR,ν max (cm -1 ): 1727 (C=O), 1125 (C-O-C).

[0029] 1 H NMR, δ H(ppm): 8.061 (1H, s, HCO), 4.273 (2H, t, J 1 =J 2 =4.6Hz, 13- CH 2 ), 3.614(2H,t,J 1 =J 2 =4.6Hz, 12- CH 2 ),3.440(2H,m, 11- CH 2 ),2.282(1H,m, 2- CH), 2.052(1H,m, 7- CH),1.918~1.801(5H,m, 10- CH 2,3- CH, 5- CH, 1- CH),1.663(2H,m, 4- CH 2 ),1.438(1H,m, 3- CH),1.143(3H,s, 9- CH 3 ),0.972(3H,s, 8- CH 3 ),0.853(1H,d, J=9.2Hz, 7- CH);

[0030] 13 C NMR, δ C (ppm): 70.228 (C -12 ), 68.203 (C -11 ), 63.054 (C -13 ), 46.298 (C -2 ), 41.322(C -5 ), 38.628 (C -6 ), 37.671 (C -1 ), 37.285 (C -10 ), 33.520 (C -7 ), 28.105 (C -9 ), 26.367(C -4 ...

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Abstract

The invention discloses a synthetic method of glycol mono-hydrogenated nopyl ether and carboxylic ester thereof and application thereof. The method comprises the following steps of adding hydrogenatednopyl halide and glycol into organic solvents; performing backflow reaction under the effect of hydroxide; after the reaction is completed, performing washing, drying, solvent recovery and vacuum distillation to obtain glycol mono-hydrogenated nopyl ether; then, performing backflow reaction on glycol mono-hydrogenated nopyl ether and carboxylic acid under the participation of catalysts and watercarrying agents; performing synthesis to obtain five kinds of glycol mono-hydrogenated nopyl ether carboxylic ester. The synthesized glycol mono-hydrogenated nopyl ether and the five kinds of glycol mono-hydrogenated nopyl ether carboxylic ester can be used for inhibiting plant pathogenic fungi. The compound has the advantages of safety, nontoxicity, low environment pollution and the like. The chemical reaction conditions are mild; the equipment is simple; the operation is simple and convenient; the product yield is high; the purity is high.

Description

technical field [0001] The invention belongs to the field of chemical synthesis of natural products, in particular to a synthesis method of ethylene glycol monohydronopyl ether and ethylene glycol monohydronopyl ether carboxylate compounds and the application of these compounds in antibacterial aspects. Background technique [0002] my country is a big country with turpentine resources. Turpentine has the advantages of large yield, low price and renewable, and its main components are α-pinene and β-pinene. The β-pinene content in pine turpentine turpentine is even higher than 30%, and its production is increasing year by year. Using β-pinene as the initial raw material for chemical synthesis and deep processing, the obtained products such as nopol and its derivatives, hydrogenated nopol and its derivatives (including ethers, esters, acetals and quaternary ammonium salts) Although too many biological activity tests have not been carried out, the only biological activity ass...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/16C07C69/28C07C69/08C07C41/16C07C43/13A01N37/12A01P3/00
CPCA01N37/12C07C41/16C07C67/08C07C69/16C07C69/28C07C69/08C07C43/13
Inventor 王宗德黄晶肖转泉范国荣陈尚钘王鹏廖圣良司红燕陈金珠
Owner JIANGXI AGRICULTURAL UNIVERSITY
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