A kind of preparation method of 1,4 enyne compounds

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

Active Publication Date: 2022-07-26
NANJING TECH UNIV
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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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  • A kind of preparation method of 1,4 enyne compounds
  • A kind of preparation method of 1,4 enyne compounds
  • A kind of preparation method of 1,4 enyne compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0031]

[0032] (2) After the TLC monitoring reaction was complete, the solvent was removed with a vacuum rotary evaporator, and the product was separated by thin-layer chromatography. The developing solvent was petroleum ether / ethyl acetate system, and the product was a yellow liquid (Z)-2-benzylidene- 5-Phenylpentan-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) ) propynoic acid, 0.02 mmol tetrakis(triphenylphosphine) palladium, 0.03 mmol calcium trifluoromethanesulfonate, 0.03 mmol cesium fluoride, add 2 mL N,N-dimethylacetamide, stir under nitrogen and 80°C The reaction equation is:

[0035]

[0036] (2) After the TLC monitoring reaction is complete, the solvent is removed with a vacuum rotary evaporator, and the product is separated by thin layer chromatography. The developing solvent is petroleum ether / ethyl acetate system, and the product is a pale yellow liquid (E)-4-methylbenzene yl-5-phenyl-1-penten-4-yne in 67% yield.

Embodiment 3

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

[0039]

[0040] (2) After the TLC monitoring reaction is complete, the solvent is removed with a vacuum rotary evaporator, the product is separated by thin layer chromatography, the developing solvent is petroleum ether / ethyl acetate system, and the product is a pale yellow liquid (E) 1,5-diphenyl yl-1-penten-4-yne, 76% yield.

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

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Abstract

The invention discloses a method for preparing 1,4 enyne compounds. In an inert gas atmosphere, allyl alcohol, alkynoic acid and a combined catalyst are added into an organic solvent, and the reaction is stirred at a temperature of 80-100° C. for 12-12 24h, a reaction solution was obtained; the combined catalyst was composed of organic palladium, fluoride salt and cesium fluoride, and the fluoride salt was bis-trifluoromethanesulfonimide salt or bis-trifluoromethanesulfonate; then the reaction solution was passed through water Extraction with ethyl acetate to remove part of the reaction solvent, drying and concentrating the organic phase, and purification by thin layer chromatography with petroleum ether / ethyl acetate developing solvent system to obtain 1,4-enyne compounds. The preparation method of the present invention is simple, the operation is convenient, the obtained by-products are only water and carbon dioxide, and has the characteristics of high atom economy and environmental protection; in addition, the preparation method of the present invention has low price of raw materials and a wide range of applicable substrates.

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 by dehydration and decarboxylation. Background technique [0002] 1,4-enynes are widely used reagents in organic synthesis and important structural motifs in natural products and biologically active compounds. In particular, the 1,5-aryl disubstituted 1,4-enyne compounds show highly effective pharmaceutical activity. Among them, African potato (Hypoxis rooperi) can treat various diseases in traditional medicine, and its derivative rooperol is used in traditional medicine. Anti-inflammatory effects have been demonstrated in rodents in pharmacological studies. In addition, in recent pharmacological studies, it was found that (E)-1-phenyl-5-methoxyphenyl-1-penten-4-yne had strong anticancer activity on the growth of human esophageal cancer cells. Therefore, the development of synthetic methods for 1,4-enyne compounds ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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 TECH UNIV
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