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A kind of (z)-β-selenocyanate acrylate compound and preparation method thereof

A technology of ester-based acrylate and compound, which is applied in the field of -β-selenocyanate-based acrylate compound and its synthesis, can solve the problem of no literature report on the synthesis method of similar compounds, and achieve low price, easy recycling, and compatibility good sex effect

Active Publication Date: 2020-08-04
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no literature report on related similar compounds and their synthetic methods

Method used

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  • A kind of (z)-β-selenocyanate acrylate compound and preparation method thereof
  • A kind of (z)-β-selenocyanate acrylate compound and preparation method thereof
  • A kind of (z)-β-selenocyanate acrylate compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～22

[0049] Following examples 1~22 all react by following reaction equation:

[0050]

[0051] The specific operation steps are: in a 10mL round bottom flask, add alkynoate (0.3mmol), potassium selenocyanate (1.2 equivalent, 0.36mmol, 516mg), water (1 equivalent), biomass deep eutectic solvent ChCl / Glycolic acid (5 equivalents, 1.5 mmol), and the resulting mixture was reacted in a 35W / 40KHz ultrasonic reaction device for 35 minutes. The reactant was extracted with ethyl acetate, and finally, the filtrate was concentrated with a rotary evaporator, and purified by column chromatography using petroleum ether (PE) / ethyl acetate (EA) as eluent and silica gel (200-300 mesh).

Embodiment 1

[0053] raw material: Target product:

[0054] ethyl(Z)-3-selenocyanatoacrylate: Colorless oil. Yield: 93%.

[0055] 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) .

[0056] 13 C NMR (100MHz, CDCl 3 )δ168.7, 140.9, 120.0, 105.6, 62.2, 14.1.

[0057] HRMS Calcd(EI)m / z for C 6 h 7 NO 2 Se:[M] + 204.9642,found: 204.9638.

Embodiment 2

[0059] raw material: Target product:

[0060] methyl(Z)-3-selenocyanatoacrylate: Colorless oil. Yield: 94%.

[0061] H NMR (400MHz, CDCl 3 )δ7.85(d, J=8.4Hz, 1H), 6.64(d, J=8.4Hz, 1H), 3.84(s, 3H).

[0062] 13 C NMR (100MHz, CDCl 3 )δ169.2, 141.3, 119.6, 105.5, 52.9.

[0063] 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 a method for ultrasonic-assisted synthesis of a (Z)-beta-selenocyanate acrylate compound. Under the action of ultrasonic wave, a biomass eutectic solvent catalyzes the additionreaction of propiolate, potassium selenocyanate and water to synthesize the (Z)-beta-selenocyanate acrylate compound. The (Z)-beta-selenocyanate acrylate compound has a selenocyanate functional groupwith important physiologic activity and modifiable ester groups, alkenyl groups and the like, providing an important organic intermediate for the synthesis of drugs and organic compounds; the methodhas the advantages that the raw materials are easy to obtain, reaction conditions are simple, mild, green and energy-saving, the reaction selectivity and the yield are high, and the substrate functional group compatibility is excellent.

Description

technical field [0001] The invention relates to a (Z)-β-selenocyanate-based acrylate compound and a synthesis method thereof, in particular to an ultrasonic-assisted biomass deep eutectic solvent catalyzed propiolate compound, thiocyanate and water in one step The invention relates to a method for synthesizing (Z)-beta-selenocyanate acrylate compound through addition reaction, which belongs to the technical field of organic intermediate synthesis. Background technique [0002] (Z)-β-selenocyanate-based acrylate compounds are a very important class of drugs and organic synthesis intermediate compounds due to their very important physiologically active selenium-containing functional groups and modifiable ester groups and alkenyl groups. However, there are no literature reports on related similar compounds and their synthesis methods. Contents of the invention [0003] Aiming at the relative compound of (Z)-beta-selenocyanate-based acrylate compound not seen in the prior art...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C391/00C07D307/42C07D333/16C07D317/64C07D311/72
CPCC07C391/00C07C2601/14C07C2601/16C07D307/42C07D311/72C07D317/64C07D333/16
Inventor 何卫民吴超包文虎陈平陈嘉靓
Owner HUNAN UNIV OF SCI & ENG