3, 3-difluoro-1, 5-hexadiene compound as well as preparation method and application thereof
A technology of compound and hexadiene, which is applied in the field of 3,3-difluoro-1,5-hexadiene compounds and its preparation, can solve problems such as the need for precious metals, poor substrate universality, and harsh conditions. Achieve the effect of high selectivity, simple operation and high selectivity
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Embodiment 1
[0034](1) Under a nitrogen atmosphere, add 0.2mmol α-trifluoromethylstyrene, 0.4mmol allyltrimethylsilane compound, and 0.01mmol tetrabutylammonium fluoride to a reaction tube containing 2.0mL solvent , stirring evenly with magnetic force to obtain a mixture; wherein, the α-trifluoromethylstyrene is 4-phenyl-α-trifluoromethylstyrene, and the allyltrimethylsilane compound is allyl Trimethylsilane, the solvent is 1,4-dioxane;
[0035] (2) Under a nitrogen atmosphere, place the bottom of the reaction tube in step (1) in an oil bath, and react the mixture at the bottom of the reaction tube for 12 hours at 130°C under magnetic stirring conditions, and pass the reaction product through a 200-300 mesh silica gel 2-biphenyl-3,3-difluoro-1,5-hexadiene compound 1 was obtained through column separation using an eluent with a volume ratio of ethyl acetate to petroleum ether of 1:100.
[0036] The characterization results of compound 1 are as follows Figure 1~3 As shown, among them, 1 ...
Embodiment 2
[0038] (1) Under a nitrogen atmosphere, add 0.2mmol α-trifluoromethylstyrene, 0.4mmol allyltrimethylsilane compound, and 0.01mmol tetrabutylammonium fluoride to a reaction tube containing 2.0mL solvent , magnetically stirred evenly to obtain a mixture; the α-trifluoromethylstyrene is 3-methoxycarbonyl-α-trifluoromethylstyrene, and the allyltrimethylsilane compound is allyl Trimethylsilane, the solvent is 1,4-dioxane;
[0039] (2) Under a nitrogen atmosphere, place the bottom of the reaction tube in step (1) in an oil bath, and react the mixture at the bottom of the reaction tube for 12 hours at 130°C under magnetic stirring conditions, and pass the reaction product through a 200-300 mesh silica gel column, using ethyl acetate and petroleum ether volume ratio of 1:100 eluent for column separation to obtain pure 2-3-methoxycarbonylphenyl-3,3-difluoro-1,5-hexanedi Alkenes 2.
[0040] The characterization results of compound 2 are as follows Figure 4~6 As shown, among them, 1...
Embodiment 3
[0042] (1) Under nitrogen atmosphere, add 0.2mmol α-trifluoromethylstyrene, 0.4mmol allyltrimethylsilane compound, 0.01mmol tetrabutylammonium fluoride to 2.0mL 1,4-dioxo In the hexacyclic ring, a mixture is obtained; the α-trifluoromethylstyrene is 4-methoxycarbonyl-α-trifluoromethylstyrene, and the allyl trimethylsilane compound is allyl trimethyl styrene Base silane, the solvent is 1,4-dioxane;
[0043] (2) Under a nitrogen atmosphere, react the mixture obtained in step (1) at a reaction temperature of 130°C for 12 hours, and then collect 2-4-methoxycarbonylphenyl-3,3-di Fluoro-1,5-hexadiene compound 3.
[0044] The characterization results of compound 3 are as follows Figure 7-9 As shown, among them, 1 H NMR (400MHz, CDCl 3 )δ8.02(d,J=8.4Hz,2H),7.47(d,J=8.3Hz,2H),5.87–5.60(m,2H),5.55(s,1H),5.20–4.96(m,2H ), 3.92 (s, 3H), 2.66 (td, J = 15.9, 7.1Hz, 2H) ppm; 13 C NMR (101MHz, CDCl 3 )δ166.8, 143.8(t, J=23.3Hz), 141.5, 130.0, 129.7, 128.8(t, J=5.3Hz), 128.3, 121.1(t, ...
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