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A kind of alkynyl heptanediol compound and its preparation method and application

A technology for alkynyl heptanediol and compound, which is applied in the field of alkynyl heptanediol compounds and their preparation, can solve the problem of no literature report on biological activity, and achieves simple and convenient follow-up treatment, good bactericidal activity and high yield Effect

Active Publication Date: 2021-02-02
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, there is no literature report on aralkynyl 1,3-diol compounds with symmetrical structures and their biological activities

Method used

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  • A kind of alkynyl heptanediol compound and its preparation method and application
  • A kind of alkynyl heptanediol compound and its preparation method and application
  • A kind of alkynyl heptanediol compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Synthesis of 3-methyl-1,7-diphenyl-1,6-diynyl-3,5-heptanediol.

[0084] in N 2 Under protective conditions, put newly prepared phenylacetylene magnesium bromide (0.05mol, 80mL THF) into a 250mL three-neck flask, place the flask at -15°C, stir for 5min, and pour the Grignard reagent into the constant pressure dropping funnel A mixture of 4.305 g (0.05 moL) of vinyl acetate and 40 mL of freshly distilled THF was added dropwise. Reaction exothermic, low temperature to reduce the occurrence of side reactions. Keep stirring and react for about 8h. After the reaction is complete, add saturated NH 4 The Cl solution quenches the reaction and hydrolyzes the product. With ethyl acetate (40mL×3), the organic layers were combined, washed with saturated NaCl (100mL×3), and then washed with anhydrous NaCl 2 SO 4 The organic phase was dried, filtered, and precipitated under reduced pressure with eluent petroleum ether: ethyl acetate (15:1) to obtain a white solid through column ...

Embodiment 2

[0094] Synthesis of anti-3-methyl-1,7-bis(4-methylphenyl)-1,6-diynyl-3,5-heptanediol.

[0095]

[0096] in N 2 Under protective conditions, put freshly prepared 4-methylphenylacetylene magnesium bromide (0.05mol, 80mL THF) into a 250mL three-neck flask, place the flask at -15°C, stir for 5min, and place in a constant pressure dropping funnel A mixture of 4.305 g (0.05 moL) of vinyl acetate and 40 mL of freshly distilled THF was added dropwise to the Grignard reagent. Reaction exothermic, low temperature to reduce the occurrence of side reactions. Keep stirring and react for about 8h. After the reaction is complete, add saturated NH 4 The Cl solution quenches the reaction and hydrolyzes the product. With ethyl acetate (40mL×3), the organic layers were combined, washed with saturated NaCl (100mL×3), and then washed with anhydrous NaCl 2 SO 4 The organic phase was dried, filtered, and precipitated under reduced pressure with eluent petroleum ether: ethyl acetate (15:1) t...

Embodiment 3

[0100] Synthesis of 3-methyl-1,7-bis(4-methoxyphenyl)-1,6-diynyl-3,5-heptanediol.

[0101] in N 2 Under protective conditions, put newly prepared 4-methoxyphenylacetylene magnesium bromide (0.05mol, 80mL THF) into a 250mL three-neck flask, place the flask at -15°C, stir for 5min, and drop the liquid under constant pressure A mixture of 4.305 g (0.05 moL) of vinyl acetate and 40 mL of freshly distilled THF was added dropwise to the Grignard reagent through the funnel. Reaction exothermic, low temperature to reduce the occurrence of side reactions. Keep stirring and react for about 8h. After the reaction is complete, add saturated NH 4The Cl solution quenches the reaction and hydrolyzes the product. With ethyl acetate (40mL×3), the organic layers were combined, washed with saturated NaCl (100mL×3), and then washed with anhydrous NaCl 2 SO 4 The organic phase was dried, filtered, and precipitated under reduced pressure with eluent petroleum ether: ethyl acetate (15:1) to ob...

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Abstract

An alkynyl heptanediol compound of the present invention and its preparation method and application. Its chemical name is anti- / syn-1,7-disubstituted aryl-1,6-diynyl-3,5-heptanediol, and its general structural formula is: in general formula (I), X=H 、CH 3 , OCH 3 or F; R=H or CH 3 . The present invention has the following characteristics: 1. The anti- / syn-1,7-disubstituted aryl-1,6-diynyl-3,5-heptanediol compound of the present invention having the general formula (I) is A brand-new compound with the characteristics of low price, easy access to raw materials and high activity. 2. The preparation method of the present invention can simultaneously obtain the cis and trans configurations of the compound. 3. The preparation method of the present invention has the advantages of rapid initial reaction and simple and convenient subsequent treatment. 4. In the preparation method of the present invention, step 1 is an exothermic reaction, and placing the reaction in a low-temperature environment can lower the temperature of the reaction system, make the reaction proceed mildly, and prevent side reactions from occurring. 5. The compounds of the present invention have good fungicidal activity, especially for crop bacteria.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to an alkynyl heptanediol compound and its preparation method and application. Background technique [0002] 1,3-diol compounds have certain biological activities due to their wide application in cosmetics, preservatives, spices, medicines, pesticides, etc., such as chloramphenicol and polyene macrolide antibiotics. Such as: U.S. invention patent (application number: US3667964DA), which provides a kind of "ESTERS OF 1,3DIOLS AND 1,3,5X-POLYOLS AS ADDITIVESFOR BAKED GOODS", which combines a series of aliphatic 1,3-diols The compounds can be used as additive ingredients in cosmetics and personal care products that protect them from fungi, yeasts and moulds, with the advantage of being more potent and having a good relative safety profile compared to other preservatives. [0003] Selling L.S reported 2-methyl-2-n-propyl-1,3-propanediol dicarbamate (Selling LS.J.A.M.A, 1955,1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/28C07C43/23C07C33/48C07C29/36C07C29/64C07C29/76C07C41/26C07C41/36A01N31/04A01N31/14A01P1/00
CPCA01N31/04A01N31/14C07B2200/09C07C33/28C07C33/486C07C43/23
Inventor 焦银春赵文静邓双刘万强马彩霞何林洪唐子龙
Owner HUNAN UNIV OF SCI & TECH