Method for synthesizing 1,4-naphthoquinone cyclopropane compound
A synthesis method and technology of cyclopropane, which is applied in the field of synthesis of organic compounds, can solve the problems of unfavorable industrial production and large quantities, and achieve the effects of good substrate adaptability, mild reaction conditions and low operation risk
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Embodiment 1
[0036]
[0037] Add 0.3mmol (E)-3-phenyl-1-(2-(phenylethynyl)phenyl)prop-2-en-1-one, 0.06mmol ferric chloride, 0.9mmol diiodine pentoxide to In a 15mL thick-walled pressure-resistant reaction tube, add 3mL of 1,4-dioxane as a solvent. Next, magnetic stirring was performed at 100° C. for 0.5 hours. After being cooled to room temperature, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product (in petroleum ether) was obtained by column chromatography separation as shown in the structural formula / ethyl acetate=20:1 as eluent). The material was a white solid, 68% yield.
[0038] Characterization data: 1 H NMR (500MHz, CDCl 3 ): δ8.21-8.18(m, 1H), 8.15, -8.12(m, 1H), 7.84-7.80(m, 2H), 7.27-7.24(m, 3H), 7.17-7.09(m, 5H), 6.78(d, J=7Hz, 2H), 3.69(d, J=6Hz, 1H), 3.45(d, J=6Hz, 1H)
[0039] 13 C NMR (125MHz, CDCl 3 ):δ192.73,191.06,134.48,1...
Embodiment 2
[0041]
[0042]0.3mmol (E)-1-(2-(phenylethynyl)phenyl)-3-(o-tolyl)prop-2-en-1-one, 0.06mmol iron nitrate, 0.9mmol diiodine pentoxide Add it into a 15mL thick-walled pressure-resistant reaction tube, and then add 3mL of 1,4-dioxane as a solvent. Next, magnetic stirring was performed at 100° C. for 0.5 hours. After being cooled to room temperature, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product (in petroleum ether) was obtained by column chromatography separation as shown in the structural formula / ethyl acetate=20:1 as eluent). The material was a white solid, 51% yield.
[0043] Characterization data: 1 H NMR (500MHz, CDCl 3 ): δ8.25-8.20(m, 1H), 8.17-8.12(m, 1H), 7.84-7.79(m, 2H), 7.22-7.17(m, 3H), 7.15-7.11(m, 3H), 7.06- 7.03(m, 1H), 6.86(t, J=8Hz, 1H), 6.54(d, J=8Hz, 1H), 3.87(d, J=8Hz, 1H), 3.50(d, J=8Hz, 1Hz) ,2.40(s,3H). ...
Embodiment 3
[0046]
[0047] 0.3mmol (E)-3-(2-methoxyphenyl)-1-(2-(phenylethynyl)phenyl)prop-2-en-1-one, 0.03mmol ferric chloride, 0.9 Add mmol diiodine pentoxide to a 15 mL thick-walled pressure-resistant reaction tube, and then add 3 mL of 1,4-dioxane as a solvent. Next, magnetic stirring was performed at 100° C. for 0.5 hours. After being cooled to room temperature, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product (in petroleum ether) was obtained by column chromatography separation as shown in the structural formula / ethyl acetate=20:1 as eluent). The material was a white solid in 78% yield.
[0048] Characterization data: 1 H NMR (500MHz, CDCl 3 ): δ8.23-8.19(m, 1H), 8.14-8.10(m, 1H), 7.81-7.77(m, 2H), 7.22-7.17(m, 5H), 7.13-7.10(m, 1H), 6.80 (d, J=8Hz, 1H), 6.61(t, J=8Hz, 1H), 6.52(dd, J 1 =7.5Hz,J 2 =1Hz, 1H)3.82(s, 3H), 3.77-3.74(m,...
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