Method for synthesizing ring exo-alkenol compounds
A technology for exocyclic allenols and compounds, which is applied in the field of synthesizing exocyclic allenols, can solve the problems of limited substrates and insufficient range of allene product types, and achieve good substrate applicability, mild conditions, and high reaction efficiency. Simple operation effect
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Embodiment 1
[0021] Synthesis of (3aa):
[0022]
[0023] 1a (0.2 mmol, 40 mg), 2a (0.3 mmol, 54 mg), rhodium acetate (2.6 mg, 2 mol%) and n-hexane (2 mL) were added to the reaction tube under argon protection; the reaction was then allowed to react at room temperature for 12 hours. Then add magnesium oxide 0.8g, dichloromethane (5.0mL) to the reaction flask, continue to react at 40 degrees Celsius for 3 hours, then celite suction filtration, remove the filter residue magnesium oxide, the filtrate is concentrated under reduced pressure to obtain a crude product, the crude product passes through Purification by column chromatography gave (3aa) (49.6 mg, dr>19:1, yield: 79%) as a pale yellow solid. The melting point was 165-168°C, 1 H NMR(400MHz, CDCl3)δ7.47-7.42(m,2H),7.34-7.25(m,3H),7.20-7.17(m,3H),6.94-6.92(m,2H),6.86(s,1H) ), 3.23(s, 1H), 2.58-2.34(m, 2H), 2.17(s, 3H), 1.16(t, J=7.6Hz, 3H). 13 C NMR(100MHz, CDCl3)δ204.0,202.9,162.4,141.3,141.1,132.8,128.7,128.5,128.0,127.9,127.3,125...
Embodiment 2
[0025] Synthesis of (3ab):
[0026]
[0027] 1a (0.2 mmol, 40 mg), 2b (0.3 mmol, 58 mg), rhodium acetate (2.6 mg, 2 mol%) and n-hexane (2 mL) were added to the reaction tube under argon protection; the reaction was then allowed to react at room temperature for 12 hours. Then add magnesium oxide 0.8g, dichloromethane (5mL) to the reaction flask, continue to react at 40 degrees Celsius for 3 hours, then celite suction filtration, remove the filter residue magnesium oxide, the filtrate is concentrated under reduced pressure to obtain a crude product, and the crude product passes through the column Chromatographic purification gave (3ab) (50.6 mg, dr>19:1, yield: 76%) as a pale yellow solid. The melting point was 126-128°C, 1 H NMR (400MHz, CDCl 3 )δ7.31(d,J=8.0Hz,2H),7.19-7.16(m,3H),7.09(d,J=8.0Hz,2H),6.99-6.94(m,2H),6.83(s,1H ), 3.18(s, 1H), 2.52-2.36(m, 2H), 2.30(s, 3H), 2.13(s, 3H), 1.12(t, J=7.6Hz, 3H). 13 C NMR (100MHz, CDCl 3 )δ204.0,202.8,162.1,140.9,138.2,137.8,132...
Embodiment 3
[0029] Synthesis of (3ac):
[0030]
[0031] 1a (0.2 mmol, 40 mg), 2c (0.3 mmol, 64 mg), rhodium acetate (2.6 mg, 2 mol%) and n-hexane (2 mL) were added to the reaction tube under argon protection; the reaction was then allowed to react at room temperature for 12 hours. Then add magnesium oxide 0.8g, dichloromethane (5mL) to the reaction flask, continue to react at 40 degrees Celsius for 3 hours, then celite suction filtration, remove the filter residue magnesium oxide, the filtrate is concentrated under reduced pressure to obtain a crude product, and the crude product passes through the column Chromatographic purification gave (3ac) (42.3 mg, dr>19:1, yield: 76%) as an oily liquid,1 H NMR (400MHz, CDCl 3 )δ8.36(d,J=2.4Hz,1H),7.82(dd,J=8.4,2.4Hz,1H),7.26-7.20(m,4H),7.06-6.96(m,2H),6.90(s ,1H),3.33(s,1H),2.51-2.32(m,2H),2.18(s,3H),1.11(t,J=7.6Hz,3H). 13 C NMR (75MHz, CDCl 3 )δ202.7,202.4,162.9,151.2,146.7,141.0,136.6,136.0,132.0,129.1,128.5,127.2,124.2,117.6,104.0,77.58,1...
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