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Alkenyl nitrile compound, derivatives thereof, and synthesizing method thereof
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A synthesis method and compound technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of unavailable raw materials and low utilization rate of atoms, and achieve easy industrial production, maintain atom economy, and react The effect of mild conditions
Inactive Publication Date: 2014-04-02
PEKING UNIV
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The existing alkenyl cyanide synthesis methods all have the important defect that raw materials are not easy to obtain to varying degrees, and the utilization rate of atoms is also low, which needs to be improved
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Embodiment 1
[0032] The synthesis of embodiment 1 3-phenylacrylonitrile
[0033] Take a reaction tube, add 6.4mg ferrouschloride, 341mg 2,3-dichloro-5,6-dicyanoquinone, 0.132ml trimethylsilylazide, 59mg allylbenzene, 2ml 1,2 -Ethylene dichloride is the solvent, slowly rise from room temperature to 60°C, and the reaction is completed within 12 hours. Silica gel column separation obtained 61.1 mg of pure product with a yield of 95%.
[0034] 1 H NMR (CDCl 3 , 400MHz): δ=7.48-7.30(m, 6H), 5.87(d, J=16.8Hz, 1H); 13 C NMR (CDCl 3 , 100MHz): δ = 150.5, 133.4, 131.1, 129.0, 127.3, 118.1, 96.2; IR (neat): v = 2217, 1619, 968, 749, 690cm -1 ; MS (70eV): m / z (%) 129.0 (M + , 100).
Embodiment 2
[0035] The synthesis of embodiment 2 3-phenylacrylonitrile
[0036] Take a reaction tube, add 9mg copper acetate, 341mg 2,3-dichloro-5,6-dicyanobenzoquinone, 0.132ml trimethylsilyl azide, 59mg allylbenzene, 2ml 1,2-dichloroquinone Ethane is used as a solvent, and the temperature is slowly raised from room temperature to 60°C, and the reaction is completed within 12 hours. Silica gel column separation obtained 50.3 mg of pure product with a yield of 78%.
[0037] 1 H NMR (CDCl 3 , 400MHz): δ=7.48-7.30(m, 6H), 5.87(d, J=16.8Hz, 1H); 13 C NMR (CDCl 3 , 100MHz): δ = 150.5, 133.4, 131.1, 129.0, 127.3, 118.1, 96.2; IR (neat): v = 2217, 1619, 968, 749, 690cm -1 ; MS (70eV): m / z (%) 129.0 (M + , 100).
Embodiment 3
[0038] The synthesis of embodiment 3 3-phenylacrylonitrile
[0039] Take a reaction tube, 227mg 2,3-dichloro-5,6-dicyanobenzoquinone, 79.5mg 3-azido-1-phenylpropene, 2ml 1,2-dichloroethane as solvent, at 25°C The reaction was completed in 12 hours. Silica gel column separation obtained 63.2 mg of pure product with a yield of 98%.
[0040] 1 H NMR (CDCl 3 , 400MHz): δ=7.48-7.30(m, 6H), 5.87(d, J=16.8Hz, 1H); 13 C NMR (CDCl 3 , 100MHz): δ = 150.5, 133.4, 131.1, 129.0, 127.3, 118.1, 96.2; IR (neat): v = 2217, 1619, 968, 749, 690cm -1 ; MS (70eV): m / z (%) 129.0 (M + , 100).
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Abstract
The invention discloses an alkenyl nitrile compound, derivatives thereof, and a synthesizing method thereof. The alkenyl nitrile compound and the derivatives thereof have a structural formula represented by a general formula I. The synthesizing method comprises steps that: under the effect of an antioxidant, various iron salts and copper salts are adopted as catalysts; an allyl compound, an azidereagent and an organic solvent are mixed; and an allyl group cyanation reaction is carried out, such that the compound or a derivative is obtained. Or, under the effect of an antioxidant, an allyl azide compound is mixed with an organic solvent; and an allyl group cyanation reaction is carried out, such that the compound or a derivative is obtained. With the synthesizing method provided by the invention, atomic economy is maintained to a large extent. The method is advantaged in high yield, mild reaction condition, simple reaction equipment, suitability for industrialized productions, and the like.
Description
technical field [0001] The invention relates to an alkenyl nitrile compound and a synthesis method thereof, in particular to an alkenyl nitrile compound and a derivative thereof. The invention also relates to a synthesis method of these compounds, belonging to the field of alkenyl nitrile compounds. Background technique [0002] Alkenyl cyanide is a class of biologically active important molecular fragments that widely exist in drugs and organisms. The construction of alkenyl cyanide has always been a research direction that researchers are more interested in, and a large number of literatures have reported various construction methods of alkenyl cyanide. The synthetic method of existing alkenyl cyanide mainly contains following several: the first kind is to generate this type of compound (Likhar, Pravin R.; Roy, Moumita; Roy, Sarabindu; Subhas, M.S.; Kantam, M.Lakshmi; Sreedhar, B.Advanced Synthesis & Catalysis, 2008, 350 (13), 1968-1974); Another kind is through the react...
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