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A kind of spice based on ɑ-ionone derivative and preparation method thereof

A technology of ionone and derivatives, which is applied in the field of novel fragrances based on ɑ-ionone derivatives and their preparation, and achieves the effects of environmental friendliness, high regio- and stereoselectivity, and easy industrialization

Active Publication Date: 2021-02-02
ZHENGZHOU TOBACCO RES INST OF CNTC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, limited by the development of organic synthesis methodology, other new flavors derived from α-ionone are rarely reported.

Method used

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  • A kind of spice based on ɑ-ionone derivative and preparation method thereof
  • A kind of spice based on ɑ-ionone derivative and preparation method thereof
  • A kind of spice based on ɑ-ionone derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add ferric acetylacetonate (0.02 mmol) and ligand hexamethylphosphoric triamide (0.05 mmol) into the reaction tube, and add solvent toluene (5 ml) and α-ionone ( 0.5 mmol), placed at 0°C, and under stirring, a solution of ethylmagnesium bromide (1 mmol) in ether was added dropwise to the reaction tube, and the reaction was continued at 0°C. After 3 hours, gas chromatography detected that the reaction was complete, cooled the reaction tube to -20 degrees, slowly added acetyl chloride solution (1 mmol), and continued to maintain the temperature for 1 hour after the dropwise addition, and then added saturated ammonium chloride solution dropwise The reaction was quenched, returned to room temperature and water was added. Extract with ether, wash the organic phase with 1% hydrochloric acid, saturated sodium bicarbonate and saturated brine successively, then dry with anhydrous sodium sulfate, filter, concentrate, flash column chromatography to obtain 3-(1-(2, 6,6-trimethyl-2...

Embodiment 2

[0028] Add ferric chloride (0.02 mmol) and ligand triphenylphosphine (0.2 mmol) into the reaction tube, and add solvent diethyl ether (5 ml) and α-ionone (1 mmol ), placed at a temperature of -10 degrees, and added dropwise a tetrahydrofuran solution of ethylmagnesium chloride (1.5 mmol) to the reaction tube under stirring, and continued the reaction at -10 degrees. After 6 hours, gas chromatography detected that the reaction was complete, cooled the reaction tube to -20 degrees, slowly added acetyl chloride solution (1.5 mmol), and continued to maintain the temperature for 1 hour after the dropwise addition, and then added saturated ammonium chloride solution dropwise The reaction was quenched, returned to room temperature and water was added. Extract with ether, wash the organic phase with 1% hydrochloric acid, saturated sodium bicarbonate and saturated brine successively, then dry with anhydrous sodium sulfate, filter, concentrate, flash column chromatography to obtain 3-(1...

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Abstract

The invention discloses a novel fragrance based on ɑ-ionone derivatives and a preparation method thereof. The chemical name of the novel fragrance is 3-(1-(2,6,6-trimethyl-2-cyclohexene-1- base) propyl-2,4-pentanedione, the structure of which is shown in formula 1. The spice has a more delicate woody aroma. The present invention firstly uses an iron catalyst to catalyze the synthesis of ɑ-Grignard reagent under the action of a ligand. Ionone carries out high regio- and stereoselective 1,4-addition reaction, and then uses acetyl chloride to capture the reaction intermediate, and finally prepares this compound. This method is simple to operate, and the raw materials and reagents are easy to obtain, and has good industrial application prospects .

Description

technical field [0001] The invention belongs to the field of fragrance chemistry, and specifically relates to a novel fragrance based on α-ionone derivatives and a preparation method thereof. Background technique [0002] Compared with natural fragrances, synthetic fragrances have the advantages of definite ingredients, stable supply, and independent of seasons. Therefore, the development of synthetic fragrances has always been an important direction for the development of new fragrances in the flavor and fragrance industry. Starting from natural fragrance compounds, using organic synthesis to modify the structure and retain its main skeleton is a method to develop new fragrance compounds. For example, α-ionone has a powdery-sweet floral aroma characteristic of violet flowers, with a woody undertone, and is a very widely used natural fragrance (Xie Jianping. Tobacco Fragrance Raw Materials. Beijing: Chemical Industry Press, 2009). Some studies have found that starting from ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/00C07C45/42C07C45/45C07C49/21A24B3/12
CPCA24B3/12C07C49/21
Inventor 柴国璧范武张启东席辉孙世豪刘珊张文娟卢斌斌李鹏曾世通刘俊辉毛健
Owner ZHENGZHOU TOBACCO RES INST OF CNTC
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