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Preparation method of 1, 4 enyne compound

A compound, enyne technology, applied in the field of organic chemical synthesis, can solve problems such as poor economy and unfriendly environment, and achieve the effects of convenient operation, low preparation cost and high atom economy

Active Publication Date: 2021-10-26
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The primary purpose of the present invention is to provide a method for preparing 1,4-enynes, aiming to solve the problems that the existing synthesis methods of 1,4-enynes are unfriendly to the environment and poor in economy

Method used

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  • Preparation method of 1, 4 enyne compound
  • Preparation method of 1, 4 enyne compound
  • Preparation method of 1, 4 enyne compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) In a 10mL Shrek tube, under nitrogen atmosphere, add 0.4mmol 2-(hydroxy(phenyl)meth)acrylate, 0.6mmol phenylpropylic acid, 0.015mmol tetrakis(triphenylphosphine)palladium , 0.04mmol calcium bistrifluoromethanesulfonimide, 0.04mmol cesium fluoride, add 4mL dimethyl sulfoxide, stir and react under nitrogen and 100°C, the reaction equation is:

[0031]

[0032] (2) After TLC monitors that the reaction is complete, remove the solvent with a vacuum rotary evaporator, and separate the product by thin-layer chromatography. The developing agent is petroleum ether / ethyl acetate system, and the product is yellow liquid (Z)-2-benzylidene- 5-Phenylpent-4-acid methyl ester, yield 79%.

Embodiment 2

[0034] (1) In a 10mL Shrek tube, under nitrogen atmosphere, add 0.3mmol 1-(4-methylphenyl)prop-2-en-1-ol, 0.45mmol 3-(3-methoxyphenyl ) propiolic acid, 0.02mmol tetrakis(triphenylphosphine) palladium, 0.03mmol calcium trifluoromethanesulfonate, 0.03mmol cesium fluoride, add 2mL N,N-dimethylacetamide, stir under nitrogen at 80°C reaction, the reaction equation is:

[0035]

[0036] (2) After TLC monitors that the reaction is complete, remove the solvent with a vacuum rotary evaporator, and separate the product by thin-layer chromatography. The developing agent is petroleum ether / ethyl acetate system, and the product is light yellow liquid (E)-4-methylbenzene Base-5-phenyl-1-penten-4-yne, yield 67%.

Embodiment 3

[0038] (1) In a 10mL Shrek tube, under nitrogen atmosphere, add 0.35mmol cinnamyl alcohol, 0.5mmol 3-(3,4-dimethoxyphenyl) propynoic acid, 0.015mmol tetrakis(triphenylphosphine) Palladium, 0.035mmol calcium bistrifluoromethanesulfonimide, 0.035mmol cesium fluoride, add 3mL ethylene glycol dimethyl ether, stir and react under nitrogen at 90°C, the reaction equation is:

[0039]

[0040] (2) After TLC monitors that the reaction is complete, remove the solvent with a vacuum rotary evaporator, and separate the product by thin-layer chromatography. The developer is petroleum ether / ethyl acetate system, and the product is a light yellow liquid (E) 1,5-diphenyl Base-1-penten-4-yne, yield 76%.

[0041] (E) 1,5-diphenyl-1-pentene-4-yne was detected by nuclear magnetic resonance, as attached Figure 1~2 shown, with figure 1 is (E) 1,5-diphenyl-1-pentene-4-yne H NMR spectrum, attached figure 2 It is the carbon nuclear magnetic resonance spectrum of (E) 1,5-diphenyl-1-penten-4-yne....

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Abstract

The invention discloses a preparation method of a 1, 4 enyne compound, which comprises the following steps of in an inert gas atmosphere, adding allyl alcohol, acetylenic acid and a combined catalyst into an organic solvent, and stirring and reacting for 12-24 hours at the temperature of 80-100 DEG C to obtain a reaction solution, wherein the combined catalyst is prepared from organic palladium, villiaumite and cesium fluoride, and the villiaumite is bis (trifluoromethanesulfonimide) salt or bis (trifluoromethanesulfonate), and extracting the reaction solution by using water and ethyl acetate to remove part of the reaction solvent, drying and concentrating an organic phase, and purifying by using a petroleum ether / ethyl acetate developing solvent system through thin layer chromatography to obtain the 1, 4-eneyne compound. The preparation method is simple and convenient to operate, the obtained by-products only comprise water and carbon dioxide, and the method has the advantages of being high in atom economy and environmentally friendly; in addition, the preparation method is low in raw material price and wide in applicable substrate range.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a method for directly synthesizing 1,4-enyne compounds through dehydration and decarboxylation. Background technique [0002] 1,4-Enynes are versatile reagents in organic synthesis and important structural motifs in natural products and bioactive compounds. In particular, 1,5-aryl disubstituted 1,4-enyne compounds show high drug activity. Among them, African potato (Hypoxis rooperi) can treat various diseases in traditional medicine, and its derivative rooperol is in Anti-inflammatory effects have been demonstrated in rodents in pharmacological studies. In addition, pharmacological studies in recent years have found that (E)-1-phenyl-5-methoxyphenyl-1-penten-4-yne has strong anticancer activity on the growth of human esophageal cancer cells. Therefore, the development of synthetic methods for 1,4-enyne compounds has aroused great concern in the synthetic community. ...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/606C07C1/20C07C15/54C07C41/30C07C43/215C07J1/00
CPCC07C67/343C07C1/20C07C41/30C07J1/0066C07C69/606C07C15/54C07C43/215
Inventor 解沛忠邱菊
Owner NANJING UNIV OF TECH
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