A meta-alkenyl or aryl substituted phenol compound and its preparation method and application
A phenol compound and compound technology, which are applied in the field of meta-alkenyl or aryl substituted phenol compounds and their preparation, can solve the problems of low synthesis efficiency, poor atom and step economy, etc., and achieve good compatibility and catalyst. Inexpensive, readily available, mild reaction conditions
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0036] Synthesis of meta-alkenyl-substituted phenol compounds represented by formula I-1:
[0037]
[0038]Under nitrogen protection, p-quinol III-1 (14.9 mg, 0.12 mmol), trans-β-styreneboronic acid II-1 (14.8 mg, 0.10 mmol), and catalyst tartaric acid (3 mg, 0.10 mmol) were successively added to a 10 mL reaction flask. 0.02 mmol) and solvent dichloromethane (1 mL), acetonitrile (0.1 mL). After the reaction solution was stirred in an oil bath at 50°C for 48 hours, TLC detected that the reaction of the raw materials was basically completed, and the reaction was stopped. The reaction solution was spin-dried and then subjected to direct column chromatography with eluent (ethyl acetate / petroleum ether=1 / 9) to obtain 16.3 mg of a white solid of formula I-1 with a yield of 78%.
[0039] Characterization data of meta-alkenyl-substituted phenol compounds represented by formula I-1: 1 H NMR (400MHz, D 6 -Acetone)δ8.17(s,1H),7.62(d,J=7.4Hz,2H),7.40(dd,J=18.0,12.0Hz,3H),7.28(t,J=7....
Embodiment 2
[0041] Synthesis of meta-alkenyl-substituted phenol compounds represented by formula I-2:
[0042]
[0043] Under nitrogen protection, p-quinol III-1 (14.9 mg, 0.12 mmol) and trans-2-(4-bromophenyl) vinylboronic acid II-2 (22.6 mg, 0.10 mmol) were sequentially added to a 10 mL reaction flask. ), catalyst tartaric acid (3 mg, 0.02 mmol) and solvent dichloromethane (1 mL), acetonitrile (0.1 mL). After the reaction solution was stirred in an oil bath at 50°C for 48 hours, TLC detected that the reaction of the raw materials was basically completed, and the reaction was stopped. The reaction solution was spin-dried and then directly column chromatographed with eluent (ethyl acetate / petroleum ether=1 / 9) to obtain 17.9 mg of a white solid of formula I-2 with a yield of 62%.
[0044] Characterization data of meta-alkenyl-substituted phenol compounds represented by formula I-2: 1 H NMR (400MHz, CDCl 3 )δ7.50-7.45(m, 2H), 7.38-7.34(m, 2H), 7.25(d, J=16.1Hz, 1H), 7.06(d, J=2.7Hz, 1...
Embodiment 3
[0046] Synthesis of meta-alkenyl-substituted phenol compounds represented by formula I-3:
[0047]
[0048] Under nitrogen protection, p-quinol III-1 (14.9 mg, 0.12 mmol) and trans-2-(3-methylphenyl)vinylboronic acid II-3 (16.2 mg, 0.10 mmol) were sequentially added to a 10 mL reaction flask. , catalyst tartaric acid (3 mg, 0.02 mmol) and solvent dichloromethane (1 mL), acetonitrile (0.1 mL). After the reaction solution was stirred in an oil bath at 50°C for 48 hours, TLC detected that the reaction of the raw materials was basically completed, and the reaction was stopped. The reaction solution was spin-dried and then subjected to direct column chromatography with eluent (ethyl acetate / petroleum ether=1 / 9) to obtain 15.3 mg of a white solid of formula I-3 with a yield of 68%.
[0049] Characterization data of meta-alkenyl-substituted phenol compounds represented by formula I-3: 1 H NMR (400MHz, CDCl 3 )δ7.32-7.30(m, 2H), 7.25(t, J=8.0Hz, 2H), 7.09(d, J=7.7Hz, 1H), 7.07(d...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More