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Heavy turpentine longifolene derivative, preparation thereof and application

A kind of technology of alkene derivatives and derivatives, applied in the field of preparation of longleaf alkene derivatives

Inactive Publication Date: 2017-04-26
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no patents and papers on longifolene derivatives (2,2,8,8-tetramethyl-4-azatricyclo[5.4.0.1 1,9 ]Dodecan-6-ene) Description

Method used

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  • Heavy turpentine longifolene derivative, preparation thereof and application
  • Heavy turpentine longifolene derivative, preparation thereof and application
  • Heavy turpentine longifolene derivative, preparation thereof and application

Examples

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Effect test

Embodiment 1

[0024] Using isolongifolenone oxime as raw material, the Beckmann rearrangement reaction is carried out to prepare isolongifolactam, and then using isolongifolactam as raw material, the longifolene derivative can be obtained through reduction reaction, namely 2, 2,8,8-Tetramethyl-4-azatricyclo[5.4.0.1 1,9 ] Dodec-6-ene. Concrete reaction equation is as follows:

[0025]

[0026] Beckmann rearrangement reaction: the present invention uses isolongifolenone oxime as raw material to prepare the isolongifolactam through Beckmann rearrangement and reduction reaction. Further specifically: isolongifolenone oxime is added to the solvent (dichloromethane) for dissolution, and then the acid-binding agent (Et 3 N) and catalyst (POCl 3 ), the mol ratio of isolongifolenone oxime, solvent, acid-binding agent, and catalyst is: 1:10:3:2, and carrying out Beckmann rearrangement reaction can obtain described isolongifolactam under inert conditions . further, which can then be sequential...

Embodiment 2

[0029] Using isolongifolenone oxime as raw material, the Beckmann rearrangement reaction is carried out to prepare isolongifolactam, and then using isolongifolactam as raw material, the longifolene derivative can be obtained through reduction reaction, namely 2, 2,8,8-Tetramethyl-4-azatricyclo[5.4.0.1 1,9 ] Dodec-6-ene. Concrete reaction equation is as follows:

[0030]

[0031] Beckmann rearrangement reaction: the present invention uses isolongifolenone oxime as raw material to prepare the isolongifolactam through Beckmann rearrangement and reduction reaction. Further specifically: isolongifolenone oxime is added to the solvent (dichloromethane) for dissolution, and then the acid-binding agent (Et 3 N) and catalyst (POCl 3 ), the mol ratio of isolongifolenone oxime, solvent, acid-binding agent, and catalyst is: 1:13:4:2.5, and carrying out Beckmann rearrangement reaction can obtain described isolongifolactam under inert conditions . further, which can then be sequenti...

Embodiment 3

[0034] Using isolongifolenone oxime as raw material, the Beckmann rearrangement reaction is carried out to prepare isolongifolactam, and then using isolongifolactam as raw material, the longifolene derivative can be obtained through reduction reaction, namely 2, 2,8,8-Tetramethyl-4-azatricyclo[5.4.0.1 1,9 ] Dodec-6-ene. Concrete reaction equation is as follows:

[0035]

[0036] Beckmann rearrangement reaction: the present invention uses isolongifolenone oxime as raw material to prepare the isolongifolactam through Beckmann rearrangement and reduction reaction. Further specifically: isolongifolenone oxime is added to the solvent (dichloromethane) for dissolution, and then the acid-binding agent (Et 3 N) and catalyst (POCl 3 ), the mol ratio of isolongifolenone oxime, solvent, acid-binding agent, and catalyst is: 1:15:5:3, and carrying out Beckmann rearrangement reaction can obtain described isolongifolactam under inert conditions . further, which can then be sequentially...

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Abstract

The invention discloses a longifolene derivative (2, 2, 8, 8-tetramethyl-4-atrane [5. 4. 0. 11, 9] dodecane-6-alkene obtained by rearrangement and reduction reaction and by taking isolongifolene ketoxime as a raw material. Besides, bacteria such as staphylococcus aureus, Klebsiella pneumonia, Escherichia coli, bacillus proteus vulgaris and pseudomonas aeruginosa can be inhibited by the longifolene derivative, and particularly, the longifolene derivative has a superior insecticidal effect on pests such as aphids and rice planthopper.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis. In particular, it relates to the preparation method and application of longifolene derivatives. Background technique [0002] As people's awareness of environmental protection and social sustainable development continues to increase, it has become an important research topic to find and excavate new natural products from plant resources for use in medicine or agriculture. It is more and more difficult to synthesize fungicides and insecticides with good activity by traditional methods, and the synthesized fungicides often have certain toxicity, drug resistance, and environmental pollution. destructive and gradually withdraw from the market or be eliminated. [0003] Recently, it was found that 1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4α-methylene was modified from natural heavy turpentine longifolene Naphthalene-7-one (isolongifenone) has good activity on inhibiting tyrosinase ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/14A01P1/00A01P7/04
CPCC07D223/14
Inventor 朱华申利群苏健李丹妮戴忠华
Owner GUANGXI UNIV OF CHINESE MEDICINE
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