Method for preparing polysubstituted alicyclic compound
A compound, cycloaliphatic technology, applied in the field of preparing polysubstituted cycloaliphatic compounds, can solve the problems of harsh reaction conditions, diversity of reaction substrates, limited scope of application, etc.
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Embodiment 1
[0052]
[0053] N 2 To a stirred solution of (2,6-dimethylphenyl) iodide diacetate (70 mg, 0.2 mmol) in DCM (2 mL) at -78 °C was added TMSOTf (72 μL, 0.4 mmol) under protection, The mixture was stirred for 10 minutes. Then, 2-(tributylstannyl)acetonitrile (75 µL, 0.24 mmol) was added to the mixture at -78°C, and the mixture was stirred for 10 minutes. Et was added to the mixture at -78 °C 3 SiH (64 μL, 0.4 mmol), after stirring for 12 h, the mixture was passed through a short silica gel column and concentrated in vacuo. The resulting residue was separated by column chromatography (Rf=0.30, developing solvent: petroleum ether / ethyl acetate=10 / 1, v / v) to obtain a multi-substituted alicyclic compound as a light yellow oily liquid, the yield was 72%.
[0054] The target product is characterized as follows:
[0055] 1H NMR (600MHz, CDCl3): δ5.94–5.76(m,1H),5.62–5.58(m,1H), 2.94–2.76(m,2H),2.74(d,J=16.6Hz,1H),2.42 (d,J=16.6Hz,1H),1.96(s,3H),1.31(s,3H).
[0056] 13 C NMR ...
Embodiment 2
[0060]
[0061] According to the method of Example 1, 2,6-diethylphenyl) iodide diacetate replaces (2,6-dimethylphenyl) iodide diacetate, and finally the residue is obtained by column chromatography (Rf=0.35, developer: petroleum ether / ethyl acetate=10 / 1, v / v) to obtain a multi-substituted alicyclic compound as light yellow oily liquid with a yield of 81%. The target product is characterized as follows:
[0062] 1 H NMR (600MHz, CDCl 3 ):δ5.99–5.95(m,1H),5.43–5.39(m,1H), 2.95–2.77(m,2H),2.74(d,J=16.6Hz,1H),2.35(d,J=16.6 Hz,1H),2.33 –2.26(m,2H),1.80–1.72(m,1H),1.35–1.21(m,1H),1.04(t,J=7.6Hz, 3H),0.74(t,J= 7.3Hz, 3H).
[0063] 13 C NMR (151MHz, CDCl 3 ): δ146.4, 127.0, 126.3, 117.5, 105.9, 47.6, 37.0, 34.6, 32.9, 32.4, 12.0, 8.9.
[0064] IR(neat):2967,2931,2873,2247,1655,1633,1455,1293,835,736.
[0065] EI-MS: calculated for [C 12 h 16 IN]:301.0,found:300.9.
Embodiment 3
[0067]
[0068] According to the method of Example 1, (2,4,6-trimethylphenyl) iodide diacetate was replaced by (2,6-dimethylphenyl) iodide diacetate. The resulting residue was separated by column chromatography (Rf=0.33, developing solvent: petroleum ether / ethyl acetate=10 / 1, v / v) to obtain a multi-substituted alicyclic compound as a light yellow oily liquid, the yield 55%. The target product is characterized as follows:
[0069] 1 H NMR (600MHz, CDCl 3 ):δ5.33–5.29(m,1H),2.84–2.62(m,3H), 2.41(d,J=16.5Hz,1H),1.96(s,3H),1.73(s,3H),1.27( s,3H).
[0070] 13 C NMR (151MHz, CDCl 3 ): δ139.3, 132.3, 122.9, 117.8, 107.9, 44.4, 39.1, 33.3, 31.0, 30.0, 22.1.
[0071] IR(neat):2969,2924,2857,2803,2250,1638,1447,1414,1374,902,862.
[0072] EI-MS: calculated for [C 9 h 12 I(M-CH 2 CN)]: 247.1, found: 247.0.
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