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S-phenyl(Z)-3-selenocyanatoprop-2-enethioate compound and synthesis method thereof

A technology of ester-based propylene thioester and propyne thioester, which is applied in the field of organic intermediate synthesis, can solve the problems of no literature report on the synthesis method of similar compounds, and achieves low price, improved reaction yield and selectivity. wide effect

Active Publication Date: 2019-03-08
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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

Method used

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  • S-phenyl(Z)-3-selenocyanatoprop-2-enethioate compound and synthesis method thereof
  • S-phenyl(Z)-3-selenocyanatoprop-2-enethioate compound and synthesis method thereof
  • S-phenyl(Z)-3-selenocyanatoprop-2-enethioate compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～2

[0045] Following examples 1~2 carry out by following reaction:

[0046]

[0047] The specific operation steps are: in a 10mL round bottom flask, add propyne thioester (0.3mmol), potassium selenocyanate (1.2 equivalents, 0.36 mmol, 516mg), water (1 equivalents), biomass eutectic Solvent ChCl / glycolic acid (molar ratio 1:2) (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

[0049] raw material:

[0050] Target product:

[0051] S-phenyl(Z)-3-selenocyanatoprop-2-enethioate:

[0052] White solid, m.p.98-99℃. Yield: 81%.

[0053] 1 H NMR (400MHz, CDCl 3 )δ8.35(d,J=8.0Hz,1H),8.03–8.00(m,2H),7.87(d,J=8.0Hz,1H),7.68–7.64(m,1H),7.56–7.52(m ,2H).

[0054] 13 C NMR (100MHz, CDCl 3 )δ191.5, 146.6, 135.3, 134.4, 129.1, 128.7, 121.4, 107.9.

[0055] HRMS Calcd(EI)m / z for C 10 h 7 NOSe:[M] + 236.9693,found:236.9695.

Embodiment 2

[0057] raw material: Target product:

[0058] S-phenyl(Z)-3-selenocyanatoprop-2-enethioate:

[0059] Light brown solid, m.p.81-83℃, yield: 84%

[0060] 1 H NMR (400MHz, CDCl 3 )δ7.68(d, J=8.0Hz, 1H), 7.31–7.28(m, 5H), 6.91(d, J=8.0Hz, 1H), 4.25(s, 3H).

[0061] 13 C NMR (100MHz, CDCl 3 )δ191.1, 137.4, 135.9, 128.8, 128.7, 127.7, 125.2, 105.7, 33.5.

[0062] HRMS Calcd(EI)m / z for C 11 h 9 NOSSe:[M] + 282.9570,found: 282.9568.

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Abstract

The invention discloses a S-phenyl(Z)-3-selenocyanatoprop-2-enethioate compound and a synthesis method thereof. The S-phenyl(Z)-3-selenocyanatoprop-2-enethioate compound is synthesized by performing athree-component addition reaction on propinyl thioate, potassium selenocyanate and water under the catalytic action of a biomass eutectic solvent with the assistance of ultrasonic waves. The S-phenyl(Z)-3-selenocyanatoprop-2-enethioate compound has a selenocyanate active group and modifiable alkenyl and thioate groups, and provides an important organic intermediate for pharmaceutical synthesis. The method has the advantages of ready availability of raw materials, simple, convenient and mild reaction conditions, environmental friendliness, energy saving, high reaction selectivity and yield, superior substrate functional group compatibility, and higher application value.

Description

technical field [0001] The present invention relates to a kind of (Z)-beta-selenocyanate group propyne thioate compound and its synthesis method, especially a kind of ultrasonic-assisted biomass deep eutectic solvent catalyzed propyne thioate compound, thiocyanate The invention discloses a method for synthesizing (Z)-beta-selenocyanate group propylene thioate compound by one-step addition reaction of acid salt and water, which belongs to the technical field of organic intermediate synthesis. Background technique [0002] (Z)-β-selenocyanate group propylene thioester compound is a very important class of drugs and organic Synthetic intermediate compounds. 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 group propylene thioate compound not seen in the prior art, the first object of the present invention is to provide a kind of sele...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/00
CPCC07C391/00
Inventor 何卫民谢龙勇王峥陈新杰黄玉林
Owner HUNAN UNIV OF SCI & ENG