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Synthesis method and antibacterial application of endo-isocamyl formaldehyde oxime and its alkyl ether

A technology of isobornyl and formaldehyde oxime is applied in the field of chemical synthesis of natural products, and can solve the problems such as reports on the synthesis and application of endo-isobornyl formaldehyde that have not yet been seen, and achieves high product yield, simple equipment and easy operation. Effect

Active Publication Date: 2020-10-02
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are no reports on the synthesis of endo-isobornyl formaldehyde oxime and its alkyl ethers and their application in antibacterial aspects

Method used

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  • Synthesis method and antibacterial application of endo-isocamyl formaldehyde oxime and its alkyl ether
  • Synthesis method and antibacterial application of endo-isocamyl formaldehyde oxime and its alkyl ether
  • Synthesis method and antibacterial application of endo-isocamyl formaldehyde oxime and its alkyl ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of endo-isocamyl formaldehyde oxime, add 0.2 mol endo-isobornyl formaldehyde and 0.12 mol sodium bicarbonate / sodium carbonate / sodium acetate / sodium hydroxide / potassium hydroxide / triethyl ether in a 250mL Erlenmeyer flask Amine / pyridine, then add 40mL of 75% ethanol aqueous solution; dissolve 0.22mol or 0.24~0.26mol of hydroxylamine hydrochloride in 40mL of water, and slowly add it dropwise to the stirring endo-isocamyl formaldehyde solution through the dropping funnel, about 30 After the dropwise addition in 1 minute, heat the water bath to 50-60°C, take a sample after 8 hours, take the upper layer after standing, dilute it with petroleum ether, shake it up, remove the water in the lower layer, dry it with anhydrous sodium sulfate, and carry out gas chromatography analysis, if Endo-isocamyl formaldehyde can end the reaction. Ethanol and part of the water were evaporated under reduced pressure on a rotary evaporator, and extracted twice with petroleum ether (50...

Embodiment 2

[0025] Endo-isocamphoryl formaldehyde oxime ethyl ether (3a, R=C 2 h 5 ) synthesis, in a 150mL ground-mouth Erlenmeyer flask equipped with a reflux spherical condenser, add 0.02mol internal isobornyl formaldehyde oxime, 0.04mol bromoethane / chloroethane / iodoethane, 40mL benzene, 2.1 g40%Na0H aqueous solution and 0.0006mol tetra-n-butylammonium bromide were put into a magnetic stirrer, stirred and heated on a magnetic heating stirrer, and the heating temperature was 80-110°C until a small amount of reflux occurred, and a sample was taken after 4 hours. Gas chromatographic analysis followed the progress of the reaction. When there was no endo-isobornyl formaldehyde oxime in the reaction solution, stop heating, cool to room temperature under stirring, transfer the reaction solution into a separatory funnel, wash with saturated saline, Water and sodium sulfate are dried, the solvent is recovered by distillation, and the product is evaporated by vacuum distillation. Endo-isocampho...

Embodiment 3

[0028] Endo-isocamphoryl formaldehyde oxime n-propyl ether (3b, R=n-C 3 h 7 ) synthesis, in a 150mL ground-mouth Erlenmeyer flask equipped with a reflux spherical condenser, add 0.02mol internal isobornyl formaldehyde oxime, 0.04mol bromo-n-propane / chloro-n-propane / iodo-n-propane, 40mL Benzene, 2.1g of 40% NaOH aqueous solution and 0.0004mol of tetra-n-butylammonium iodide were put into a magnetic stirrer, stirred and heated on a magnetic heating stirrer, the heating temperature was 80-110°C, until a small amount of reflux occurred, 4 hours Then take a sample for gas chromatography analysis to track the progress of the reaction. When there is no endo-isocamyl formaldehyde oxime in the reaction solution, stop heating, cool to room temperature under stirring, transfer the reaction solution into a separatory funnel, and wash with saturated saline. , dried over anhydrous sodium sulfate, the solvent was recovered by distillation, and the product was evaporated by vacuum distillati...

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Abstract

The invention discloses a synthesis method and antibacterial application of endo-isobornyl formaldehyde oxime and its alkyl ether. The oximation reaction of endo-isobornyl formaldehyde and hydroxylamine hydrochloride is carried out under the action of a basic compound, and hydroxylamine hydrochloride The amount ratio of the salt and the basic compound is equivalent, and after the reaction is completed, the endo-type isobornyl formaldehyde oxime is obtained by removing the solvent, extracting, washing, drying, reclaiming the solvent, and vacuum distillation; the endo-type isobornyl formaldehyde oxime and The alkyl halide undergoes an etherification reaction under the action of a base and a phase transfer catalyst. After the reaction is completed, extraction, washing, drying, and distillation to remove the solvent are followed by vacuum distillation to obtain the alkyl ether of the endo-isocamyl formaldehyde oxime. The synthesis process is easy to operate, the product yield is high, and the purity is high; the endo-isobornyl formaldehyde oxime has a good inhibitory effect on the growth of 12 kinds of plant pathogenic fungi, and some of them exceed or even far exceed the antibacterial effect of chlorothalonil , the endo-isocamyl formaldehyde oxime alkyl ether also had a certain inhibitory effect on the growth of 6 kinds of phytopathogenic fungi.

Description

technical field [0001] The invention belongs to the field of chemical synthesis of natural products, in particular to a synthesis method and antibacterial application of endo-isocamyl formaldehyde oxime and its alkyl ether. Background technique [0002] Camphene exists in a variety of natural essential oils. It is mainly produced industrially from α-pinene, the main component of turpentine oil, through catalytic isomerization. It is an important fine chemical intermediate. Camphene can be produced through formylation reaction to produce ω-formyl camphene (containing E, Z two isomers), and then hydrogenated at high pressure under the action of palladium carbon catalyst to obtain isocamphoryl formaldehyde, in which the endo isomerism The content of isomers is more than 95%, and less than 5% is external isomers. [0003] Oxime compounds are products formed by the condensation reaction of carbonyl (C=0) and hydroxylamine (H2N-OH) in aldehydes and ketones. This is a class of com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/08C07C249/12C07C251/38A01N35/10A01P3/00
CPCA01N35/10C07C249/08C07C249/12C07C2602/42C07C251/38
Inventor 王宗德冯雪贞肖转泉陈金珠范国荣陈尚钘廖圣良罗海贺璐王鹏司红燕黎炳华
Owner JIANGXI AGRICULTURAL UNIVERSITY
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