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

The technology of a compound and alkynyl nonane, applied in the field of alkynyl nonanetriol compounds and preparation thereof, can solve the problems such as the biological activity of the triol compounds is not reported in literature and the like, and achieves simple and convenient subsequent processing, easy to obtain, low price Effect

Active Publication Date: 2021-01-29
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, there is no literature report on triol compounds containing alkyne groups and their biological activities.

Method used

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

Examples

Experimental program
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Effect test

Embodiment 1

[0061] Syn-3-methyl-1,9-bis(4-methylbenzene)-1,8-diynyl-3,5,7-nonanetriol.

[0062]

[0063] in N 2 Under protective conditions, put freshly prepared 4-methylphenylacetylene magnesium bromide (0.05mol, 80mL THF) into a 250mL three-necked 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 (8:1) to obtain a...

Embodiment 2

[0067] Syn-3-phenyl-1,9-bis(4-fluorobenzene)-1,8-diynyl-3,5,7-nonanetriol.

[0068]

[0069] in N 2 Under protective conditions, put newly prepared 4-fluorophenylacetylene magnesium bromide (0.05mol, 80mL THF) into a 250mL three-neck flask, place the flask at -15°C, stir for 5min, and pour it into the constant pressure dropping funnel A mixture of 5.006 g (0.05 moL) of isopropenyl 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 (8:1) to ...

Embodiment 3

[0073] Experiments prove that the alkynyl nonanetriol compound of the invention has good fungicidal activity on crop diseases.

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PUM

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Abstract

An alkynyl nonanetriol compound of the present invention and its preparation method and application. Its chemical name is syn-1,9-disubstituted aryl-1,8-diynyl-3,5,7-nonanetriol, and its general structural formula is: X=CH 3 or F; R=CH 3 or Ph. The present invention has the following characteristics: 1. The syn-1,9-disubstituted aryl-1,8-diynyl-3,5,7-nonanetriol compound of the present invention with general formula (I) is one 2. The preparation method of the present invention has the characteristics of cheap and easy-to-obtain synthetic materials, simple operation, mild reaction conditions and high yield. 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 nonanetriol compound and its preparation method and application. Background technique [0002] Triols are widely found in natural products such as red algae and ginseng, and have attracted widespread attention due to their wide range of applications in pesticides and medicine and certain biological activities. Such as: [0003] U.S. patent application (application number: US13805436) discloses a kind of " 5α-androstane (alkyl)-3β, the purposes of 5,6β-triol in the preparation of neuroprotective medicine ", and this compound is to cerebral ischemia, spinal cord Neuronal damage caused by ischemia or hypoxia has a significant protective effect, and there is no obvious toxic reaction within its effective dose range. It can improve the survival rate of neurons, and provides a new type of drug for the treatment of neuron diseases. [0004] In 2008, W Wang et al....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/48C07C29/36A01N31/04A01P3/00A01P1/00
CPCA01N31/04C07B2200/07C07C29/36C07C33/486
Inventor 焦银春赵文静马彩霞邓双刘万强曹晨忠
Owner HUNAN UNIV OF SCI & TECH