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3-p-menthene-1-amine and its preparation method and biological activity application

A bioactive, p-menthene technology, applied in the preparation of carboxylic acid amides, botany equipment and methods, applications, etc., can solve the problems of inapplicability, and achieve the effect of easy operation, mild reaction conditions, and strong herbicidal activity

Active Publication Date: 2017-09-12
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But, do not find the existence of the substance 3-p-mentene-1-amine of the present invention in these products of synthesizing p-menthanediamine, that is to say, the existing method of synthesizing p-menthanediamine is not suitable for the synthesis of the substance of the present invention 3-p-menthen-1-amine

Method used

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  • 3-p-menthene-1-amine and its preparation method and biological activity application
  • 3-p-menthene-1-amine and its preparation method and biological activity application
  • 3-p-menthene-1-amine and its preparation method and biological activity application

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Embodiment 1

[0049] Add 451.4mL of 7.5% HCl aqueous solution, 101.6g of N,N'-diacetyl-1,8-p-menthanediamine (400mmol ), start stirring, and heat to reflux for 8h. After the reaction, the reaction solution was cooled and allowed to stand, and the reaction solution was separated into layers. The yellow oily liquid in the upper layer was evaporated in vacuo to obtain 43 g (220.5 mmol) of a viscous yellow oily intermediate product, with a yield of 55.1%.

Embodiment 2

[0051] Add 398mL of 10% HCl aqueous solution and 101.6g (400mmol) of N,N'-diacetyl-1,8-p-menthanediamine into a 1L four-neck flask equipped with a thermometer, condenser and mechanical stirrer , started stirring, and heated to reflux for 8h. After the reaction, the reaction solution was cooled and allowed to stand, and the reaction solution was separated into layers. The yellow oily liquid in the upper layer was evaporated in vacuo to obtain 43.9 g (225.2 mmol) of a viscous yellow oily intermediate product, with a yield of 56.3%.

Embodiment 3

[0053] Add concentration of 20% H 2 SO 4 460 mL of aqueous solution, 101.6 g (400 mmol) of N,N'-diacetyl-1,8-p-mentanediamine, started stirring, and heated to reflux for 10 h. After the reaction, the reaction solution was cooled and allowed to stand, and the reaction solution was separated into layers. The yellow oily liquid in the upper layer was evaporated in vacuo to obtain 41.4 g (212.3 mmol) of a viscous yellow oily intermediate product, with a yield of 53.1%.

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Abstract

The invention discloses 3-p-menthene-1-amine as well as a preparation method and a bioactive application thereof. The preparation method comprises steps as follows: N,N'-diacyl-1,8-diamino-p-menthane is dissolved in a strongly acidic aqueous solution, stirred, subjected to a heating reflux reaction and then allowed to stand for layering; a yellow oily liquid on the upper layer is transferred into another reaction flask, an appropriate amount of ethylene glycol and strong alkali is added, a mixture starts to be stirred, part of substances with a low boiling point are removed through heating, then the temperature is increased, a condenser pipe is mounted, and the heating reflux reaction is performed; after the reaction, extraction is performed with ethyl acetate; water is added to an organic layer obtained through extraction, and pH is regulated to be acidic; an aqueous phase is taken, pH is regulated to be 9-11 with alkali, and the aqueous phase is subjected to layering; a yellow transparent liquid on the upper layer is 3-p-menthene-1-amine and is subjected to reduced-pressure distillation and purification. The reaction conditions are relatively mild and non-toxic, the operation is easy, and the raw materials are easy to synthesize. Prepared 3-p-menthene-1-amine has certain bacteriostatic activity and herbicidal activity.

Description

Technical field: [0001] The invention relates to biologically active 3-p-menthene-1-amine and a preparation method thereof, in particular to using N,N'-di(ethyl)acyl-1,8-p-menthanediamine as a raw material through N-( B) A method for preparing 3-p-menten-1-amine from an acyl-3-p-menten-1-amine intermediate compound, and its application as a herbicidal active substance and a bacteriostatic active substance. Background technique [0002] 3-p-menthene-1-amine is a monoterpene amine derivative, which is a colorless and transparent liquid at room temperature. It consists of two parts, p-menthene and amine groups, and contains two active groups: carbon Carbon double bond and amine group, wherein the amine group on the ring is easy to react with aldehyde, acid anhydride or acid chloride to generate the corresponding Schiff base, amic acid or amide derivatives. According to literature reports, compounds containing p-menthene skeletons often have strong biological activity, and some...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/62C07C209/86C07C211/40C07C231/12C07C233/06A01N33/04A01P13/00A01P1/00A01P3/00
CPCA01N33/04C07C209/62C07C209/86C07C211/40C07C231/12C07C233/06
Inventor 赵振东朱守记徐士超陈玉湘李冬梅毕良武王婧古研卢言菊
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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