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Isolongifolenone oxime ether derivative, and preparation method and application thereof

A kind of technology of leaf ketene oxime ether and isolongifole ketone, which is applied in the field of isolong leaf ketene oxime ether derivatives and preparation thereof

Active Publication Date: 2017-04-19
广西鼎弘树脂有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are no patents and papers describing isolongifolene oxime ether

Method used

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  • Isolongifolenone oxime ether derivative, and preparation method and application thereof
  • Isolongifolenone oxime ether derivative, and preparation method and application thereof
  • Isolongifolenone oxime ether derivative, and preparation method and application thereof

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Embodiment 1

[0027] The present invention uses isolongifolenone as a raw material, synthesizes isolongifolenone oxime through addition elimination reaction, and then performs an alkylation reaction on isolongifolenone oxime to prepare the isolongifolenone oxime ether derivative things.

[0028] The specific overall reaction equation is as follows:

[0029]

[0030] R is an alkane group or an arene group.

Embodiment 2

[0032] Compound 1: O-(1,2-Epoxy Propyl)1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H- 2,4a-Methanonaphthalen-7-one oxime-ether): preparation.

[0033] Addition Elimination Reaction: Using isolongifolenone as raw material, isolongifolenone oxime was synthesized by addition elimination reaction. Further specifically: using isolongifolenone and hydroxylamine hydrochloride as reactants, organic alcohol (methanol) and deionized water as solvents, and inorganic base (sodium carbonate) to remove the acid generated in the reaction, wherein isolongifolenone The molar ratio of hydroxylamine hydrochloride and inorganic base is: 1:0.1:0.1, and the isolongifolenone oxime can be obtained by carrying out reflux reaction. Further, extraction with ethyl acetate, washing and drying with saturated brine and deionized water in sequence, and then concentration and drying can obtain isolongifolenone oxime crystals.

[0034] Alkylation reaction: using isolongifolenone oxime and epichlorohydrin as r...

Embodiment 3

[0040] Compound 2: Ethyl isolongifolene oxime ether (O-Ethyl 1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4a-MethanonaPht-halen- 7-one oxime-ether) preparation.

[0041]Addition Elimination Reaction: Using isolongifolenone as raw material, isolongifolenone oxime was synthesized by addition elimination reaction. Further specifically: using isolongifolene and hydroxylamine hydrochloride as reactants, organic alcohol (ethanol) and deionized water as solvent, and inorganic base (sodium hydroxide) to remove the acid produced in the reaction, wherein isolongifolene The molar ratio of ketone, hydroxylamine hydrochloride and inorganic base is: 1:0.3:0.2, and the isolongifolenone oxime can be obtained by carrying out the reflux reaction. Further, extraction with ethyl acetate, washing and drying with saturated brine and deionized water in sequence, and then concentration and drying can obtain isolongifolenone oxime crystals.

[0042] Alkylation reaction: using isolongifolene oxime ...

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Abstract

An isolongifolenone oxime ether derivative is prepared by the following steps of: taking isolongifolenone as the raw material, synthesizing isolongifolenone oxime through addition-elimination reaction, and performing alkylation reaction of the isolongifolenone oxime. Simultaneously, the isolongifolenone oxime ether derivative disclosed by the invention can inhibit bacteria, such as staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, bacillus proteus vulgaris and pseudomonas aeruginosa, and fungus, such as Aspergillus niger, exserohilum turcicum, corn sheath blight, alternaria musae Bovr.et Bat. and colletotrichum musae; and the isolongifolenone oxime ether derivative has the excellent insecticidal action for insect pests, such as aphid and rice planthopper.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. It particularly relates to isolongifolene oxime ether derivatives and their preparation methods and applications. Background technique [0002] As people's awareness of environmental protection and social sustainable development continues to increase, especially in the 21st century, finding and excavating new natural medicines from plant resources for use in medicine or agriculture has become an important research topic around the world. It is more and more difficult to synthesize fungicides with good activity by traditional synthesis methods, and the fungicides synthesized often have certain toxicity, drug resistance and environmental pollution. Environmental damage is strong and gradually withdraw from the market or be eliminated. Therefore, the research and development and creation of new drugs with independent property rights have become a hot spot in the research of medicine and ...

Claims

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Application Information

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IPC IPC(8): C07C249/12C07C251/44C07D301/28C07D303/22A01N43/20A01N35/10A01P1/00A01P3/00A01P7/04
CPCA01N35/10A01N43/20C07C249/08C07C249/12C07D301/28C07D303/22C07C251/44
Inventor 申利群吴爱群张武颜秀阳邱森森雷福厚
Owner 广西鼎弘树脂有限公司
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