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Citral diborneol-based acetal derivative and preparation method and application thereof

A technology of citral dimethyl acetal and citral, which is applied in the field of citral dibornyl acetal derivatives and their preparation, can solve the problems of strong volatility, low efficacy, poor solubility and the like, and achieves mild reaction conditions , low difficulty, stable derivatives

Active Publication Date: 2018-09-21
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Borneol is divided into natural borneol and synthetic borneol. Borneol has pharmacological activities such as anti-inflammatory, bactericidal, analgesic, and anti-oxidant. However, when borneol is used as a single herb, it has disadvantages such as low efficacy, strong volatility, and poor solubility.

Method used

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  • Citral diborneol-based acetal derivative and preparation method and application thereof
  • Citral diborneol-based acetal derivative and preparation method and application thereof
  • Citral diborneol-based acetal derivative and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0058] A kind of preparation of citral dibornyl acetal derivatives, such as figure 1 shown, including the following steps:

[0059] (1) At room temperature, take by weighing citral 7.6120g (0.05mol, molecular weight 152.23), trimethyl orthoformate 21.2240g (0.20mol, molecular weight 106.12) in a dry clean round bottom flask, dissolve in 50mL of methanol, Add 28.56mg of p-toluenesulfonic acid, and the reaction system is refluxed at 80°C and 800r / min for 6 hours;

[0060] (2) Add saturated sodium bicarbonate aqueous solution to the reaction system in batches to pH=7-8, remove p-toluenesulfonic acid, concentrate under reduced pressure, extract 3 times with 30mL dichloromethane, collect the organic layer, add 9.4522g anhydrous sulfuric acid Sodium dehydration for 6 hours;

[0061] (3) Remove anhydrous sodium sulfate by filtration, remove the solvent under reduced pressure, and use a silica gel column with an average particle size of 48 μm for analysis: first, dissolve the silica g...

Embodiment 2

[0071] (1) At room temperature, weigh 3.8221g (0.025mol) of citral and 10.3421g (0.097mol) of trimethyl orthoformate in a dry and clean round bottom flask, dissolve them in 40mL of methanol, and add 15.21mg of p-toluenesulfonate acid, the reaction system was refluxed at 75°C and 800r / min for 4 hours.

[0072] (2) Add saturated aqueous sodium bicarbonate solution to pH = 7-8 in batches to the reaction system, remove p-toluenesulfonic acid, concentrate under reduced pressure, extract 3 times with 30 mL of dichloromethane, collect the organic layer, add 5.3214 g of anhydrous sulfuric acid Sodium dehydration for 4 hours.

[0073] (3) Remove anhydrous sodium sulfate by filtration, remove the solvent under reduced pressure, and use a silica gel column with an average particle diameter of 37 μm for analysis. : 1) flushing with eluent, wash out the impurities with low polarity first, and then elute with the solution obtained by mixing sherwood oil and ethyl acetate at a volume ratio ...

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PUM

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Abstract

The invention discloses a citral diborneol-based acetal derivative and a preparation method and application thereof. The structural formula of the citral diborneol-based acetal derivative is shown asthe formula I. According to the citral diborneol-based acetal derivative, citral dimethylacetal and borneol are subjected to distilling reacting under the action of a catalyst, and the citral diborneol-based acetal derivative is obtained. The citral diborneol-based acetal derivative is stable, and the mold resistance of the citral diborneol-based acetal derivative is far superior to that of borneol and citral. The citral diborneol-based acetal derivative further has an acid-sensitive character, and therefore the citral diborneol-based acetal derivative has a certain officinal function of controlling releasing at the same time, and can be applied to preparing acid-sensitive micromolecular medicine monomers. The raw materials and reagents adopted in the citral diborneol-based acetal derivative are all simple and easy to obtain, the reaction conditions are mild, the operation method is not high in difficulty, and the product has wide application prospects in the fields of organic chemistry and medicine. The formula is shown in the description.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a citral dibornyl acetal derivative and its preparation method and application. Background technique [0002] Borneol, also known as plum slices and borneol, is a dicyclic monoterpene alcohol. Borneol is divided into natural borneol and synthetic borneol. Borneol has pharmacological activities such as anti-inflammatory and bactericidal, analgesic, and anti-oxidant. However, when borneol is used as a single herb, it has disadvantages such as low efficacy, strong volatility, and poor solubility. [0003] How to further transform the borneol, overcome its shortcomings, give play to its advantages, and make it have a wider range of uses, this is a problem to be solved. Contents of the invention [0004] The primary purpose of the present invention is to overcome the shortcomings and deficiencies of the prior art and provide a citral dibornyl acetal derivative. [0005] Another ob...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/303C07C41/56C07C29/10C07C35/30C07C45/42C07C47/21A61P31/04
CPCA61P31/04C07C29/10C07C43/303C07C45/42C07C2602/42C07C35/30C07C47/21
Inventor 苏健裕喻阿坤覃业霞徐振波李冰张霞李琳王丽
Owner SOUTH CHINA UNIV OF TECH
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