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Environment-friendly preparation method of Z-3-thiocyanate acrylate compound

A technology of ester-based acrylate and Z-3-, which is applied in the field of environmental protection preparation of Z-3-selenocyanate-based acrylate compounds, can solve the problems of no commercial products, complicated separation process, environmental pollution and the like, and achieves Avoid the complex separation and purification process, high catalytic activity, and the effect of shortening the reaction time

Inactive Publication Date: 2019-06-21
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, there is a deep eutectic solvent to catalyze the three-component reaction of propiolate, selenocyanate and water to obtain Z-3-selenocyanate-based acrylate compounds, such as (ACS Sustainable Chem. Eng.2019 ,7,2169-2175), but the reaction also has the following shortcomings, which limit its practical application:
[0003] 1) The deep eutectic solvent needs to be prepared, and there is no commercial product
[0004] 2) The yield of Z-3-selenocyanate-based acrylate compound is 77-94%, and there are E-form isomers and propiolic acid ester decomposition products propiolic acid and unreacted propiolate in the reaction Raw materials, low purity
[0005] 3) The separation of the product needs to be extracted with a volatile organic solvent, and the purification of the product needs to be separated by silica gel column chromatography. The separation process is not only complicated and costly, but also causes environmental pollution

Method used

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  • Environment-friendly preparation method of Z-3-thiocyanate acrylate compound
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  • Environment-friendly preparation method of Z-3-thiocyanate acrylate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～22

[0053] Following examples 1~22 all react by following reaction equation:

[0054]

[0055] The specific operation steps are: in a 20mL reaction tube, sequentially add propiolate (10mmol), potassium selenocyanate (12mmol, 1.16g), water (10mmol, 0.18g), lactic acid (30mmol, 2.70g), and mix the obtained The solution was reacted in a 30W / 44KHz ultrasonic reaction device for 30 minutes. After the reaction, 13.5ml of water and lactic acid were added to form a lactic acid aqueous solution, and the Z-3-selenocyanate-based acrylate compound was insoluble in the lactic acid aqueous solution, precipitated, separated, and vacuum-dried to calculate the weight.

Embodiment 1

[0057] raw material: Target product:

[0058] ethyl(Z)-3-selenocyanatoacrylate: Colorless oil. Yield: 93%.

[0059] 1 H NMR (400MHz, CDCl 3 )δ7.82(d, J=8.4Hz, 1H), 6.62(t, J=8.4Hz, 1H), 4.28 (q, J=7.2Hz, 2H), 1.33(t, J=7.2Hz, 3H) .

[0060] 13 C NMR (100MHz, CDCl 3 )δ168.7, 140.9, 120.0, 105.6, 62.2, 14.1.

[0061] HRMS Calcd(EI)m / z for C 6 h 7 NO 2 Se:[M] + 204.9642,found: 204.9638.

Embodiment 2

[0063] raw material: Target product:

[0064] methyl(Z)-3-selenocyanatoacrylate: Colorless oil. Yield: 94%.

[0065] H NMR (400MHz, CDCl 3 )δ7.85(d, J=8.4Hz, 1H), 6.64(d, J=8.4Hz, 1H), 3.84 (s, 3H).

[0066] 13 C NMR (100MHz, CDCl 3 )δ169.2, 141.3, 119.6, 105.5, 52.9.

[0067] HRMS Calcd(EI)m / z for C 5 h 5 NO 2 Se:[M] + 190.9486,found:190.9485.

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Abstract

The invention discloses an environment-friendly preparation method of a Z-3-thiocyanate acrylate compound. The green preparation method comprises the following steps: under the action of ultrasonic waves, carrying out three-component addition reaction on a lactic acid catalytic propiolate compound, thiocyanate and water to generate the Z-3-thiocyanate acrylate compound; after the reaction is ended, adding water into a system for diluting, thus separating out a high-purity Z-3-thiocyanate acrylate product. The method has the advantages of good product selectivity, high yield, simple separationprocess, low catalyst cost, environment friendliness and facilitation for industrial production and application.

Description

technical field [0001] The present invention relates to an environment-friendly preparation method of Z-3-selenocyanate-based acrylate compound, in particular to a method for synthesizing Z by one-step addition reaction of propiolate compound, potassium selenocyanate and water catalyzed by ultrasonic wave-assisted lactic acid A method for 3-selenocyanate-based acrylate compounds, which belongs to the technical field of organic intermediate synthesis. Background technique [0002] Z-3-selenocyanate acrylate compounds not only have very important physiological activities, but also contain selenocyanate functional groups, ester groups, and alkenyl groups, which are all important modifiable functional groups, and are a very important class of drugs. And organic synthesis intermediate compounds. In the prior art, there is a deep eutectic solvent to catalyze the three-component reaction of propiolate, selenocyanate and water to obtain Z-3-selenocyanate-based acrylate compounds, s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/00B01J31/04
Inventor 何卫民唐海姗易荣楠陈新杰张波
Owner HUNAN UNIV OF SCI & ENG