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Myrcenyl amide as well as synthesis method and applications thereof

A technology of alkenyl amide and myrcene, which is applied in the fields of amide active ingredients, carboxylic acid amide preparation, chemical instruments and methods, etc., and can solve problems such as the application research of D-A adducts without myrcene

Inactive Publication Date: 2012-10-10
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, Goldblatt, Yin and Luo Jinyue all studied the Diels-Alder reaction, but they did not study the application of the D-A adduct of myrcene in industry

Method used

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  • Myrcenyl amide as well as synthesis method and applications thereof
  • Myrcenyl amide as well as synthesis method and applications thereof
  • Myrcenyl amide as well as synthesis method and applications thereof

Examples

Experimental program
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Embodiment 1

[0031] The first step, the Diels-Alder reaction

[0032] Equipped with a water bath, a stirring device, a thermometer, a dropping funnel and a reflux condenser (the condenser is connected to a built-in CaCl 2 In the 250mL four-necked flask of drying tube), add dimethyl maleate 72g. Start the stirrer, add equimolar myrcene dropwise from the dropping funnel, and after the dropwise addition, raise the temperature to 150°C for 3 hours of reaction. After the reaction is over, vacuum distillation is used to extract the fraction at 205°C / 1.05kPa (absolute pressure), and the remainder is the compound 4-(4-methyl-3-pentenyl)-4-cyclohexene-1,2- Dimethyl dicarboxylate, weighing 119.7g, yield 88.1%, pale yellow liquid.

[0033] The second step, ammonolysis reaction

[0034] Add 11.8 g of dimethyl 4-(4-methyl-3-pentenyl)-4-cyclohexene-1,2-dicarboxylate into a 150 mL stainless steel reactor, and add 9.3 g of anhydrous CaCl 2 and 60 mL of anhydrous CH 3 OH, put it in an ice-water bath a...

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Abstract

The invention discloses myrcenyl amide as well as a synthesis method and applications thereof. The synthesis method comprises two steps: step one, carrying out Diels-Alder reaction on myrcene and dimethyl maleate under certain conditions to obtain an intermediate product 4-(4-methyl-3-pentenyl)-4-crclohexene-1,2-dicarboxylate; and step two, carrying out ammonolysis reaction on the intermediate product and NH3 under certain conditions to generate needed 4-(4-methyl-3-pentenyl)-4-cyclohexene-1,2-diamide. The synthesis method has the characteristics of economics, short synthesis route and high productivity. Through bacteriostasis test, 4-(4-methyl-3-pentenyl)-4-cyclohexene-1,2-diamide has bacteriostasis property which is specific.

Description

1. Technical field [0001] The invention belongs to amide synthesis technology, in particular to a method for synthesizing myrcenyl amides, which is applicable to the field of synthesis of terminal amides. 2. Background technology [0002] my country is rich in turpentine resources, especially in Guangdong, Guangxi and Yunnan. Among them, Yunnan pine resin in Shuangjiang area contains up to 30.3% β-pinene. Industrially, β-pinene can produce myrcene with a purity of about 80% through thermal isomerization, and the purity can be increased to 99% after rectification. Myrcene is also known as myrcene and its chemical name is 7-methyl-3-methylene-1,6-octadiene. There are three unsaturated carbon-carbon double bonds in the molecule, which are prone to various chemical reactions, such as: Diels-Alder reaction, reduction reaction and oxidation reaction, etc. Among them, Goldblatt, Yin and Luo Jinyue all studied the Diels-Alder reaction, but they did not study the application of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/10C07C231/10C07C231/02A61K31/16A61P31/04
Inventor 夏建陵连建伟汪梅唐晓东
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY