Oxazoline ring-containing amino tocopheroxyl zinc/magnesium complexes and preparation method and application thereof
A kind of aminophenoloxyzinc, oxazoline-containing technology, applied in magnesium organic compounds, zinc organic compounds, organic chemistry and other directions, can solve the problems of low selectivity, reduced catalytic activity and the like
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Embodiment 1
[0052] Synthesis of Ligand L1:
[0053] (1) Synthesis of N-[(4R)-2-methylene-4-phenyloxazoline]benzylamine
[0054]
[0055] Add benzylamine (8.21g, 76.6mmol) and potassium carbonate (1.17g, 8.47mmol) in the reaction flask, (4R)-2-chloromethyl-4-phenyl-2-oxazoline (1.50g, 7.66mmol ) and 25mLN,N-dimethylformamide, reacted for 12 hours. The solvent and unreacted benzylamine were distilled off under reduced pressure to obtain an orange-red oil. It is directly used in the next reaction, and the yield is calculated at 80%.
[0056] (2) Synthesis of Ligand L1
[0057]N-[(4R)-2-methylene-4-phenyloxazoline]benzylamine (2.23g, 6.70mmol), potassium carbonate (1.39g, 9.84mmol), 2-bromomethyl -4,6-dichlorophenol (2.55g, 9.96mmol) and 20mL N,N-dimethylformamide were reacted at room temperature for 2 hours. Add water to quench the reaction, extract with ethyl acetate, combine the organic phases, dry over anhydrous magnesium sulfate, filter, evaporate the solvent under reduced pressu...
Embodiment 2
[0061] Synthesis of Ligand L2
[0062] N-[(4R)-2-methylene-4-phenyloxazoline]benzylamine (1.50g, 4.51mmol), potassium carbonate (0.856g, 6.19mmol) and 2-bromomethyl- Except for 4,6-di-tert-butylphenol (1.11g, 3.71mmol), other operating steps were the same as in Example 1. Separation and purification by column chromatography gave light yellow foam L2 (1.01 g, 56%).
[0063]
[0064] 1 HNMR (CDCl 3 ,400MHz,298K):δ10.12(s,1H,OH),7.37–7.25(m,11H,ArH),6.91(d,1H, 4 J=2.4Hz, ArH), 5.23 (pesudot, 1H, 3 J=9.2Hz,CH 2 O),4.63(dd,1H, 3 J=8.4Hz, 2 J=10.4Hz,CH 2 O),4.12(t,1H, 3 J=8.4Hz, CHN), 4.00(s, 2H, ArCH 2 ),3.76(s,2H,PhCH 2 ),3.44(ddd,2H, 4 J=0.8Hz, 2 J=15.6Hz, 2 J=16.0Hz, NCH 2 C=N),1.46(s,9H,C(CH 3 ) 3 ),1.29(s,9H,C(CH 3 ) 3 ). 13 CNMR (CDCl 3 ,100MHz,298K):δ165.4,154.1,142.0,140.8,137.1,136.0,129.7,128.9,128.6,127.7,126.7,124.4,123.4,121.3,74.7,69.7,58.8,57.5,13.4,34.8,35. 29.8. Anal. Calcd. ForC 32 h 40 N 2 o 2 : C, 79.30; H, 8.32; N, 5.78. Found: C, 7...
Embodiment 3
[0066] Synthesis of Ligand L3
[0067] N-[(4R)-2-methylene-4-phenyloxazoline]benzylamine (4.95g, 14.9mmol), potassium carbonate (2.80g, 20.3mmol) and 2-bromomethyl- Except for 4,6-dicumylphenol (12.98g, calculated based on a yield of 50%, the actual raw material content is about 10.38g, 15.3mmol), the other operating steps are the same as in Example 1. Separation and purification by column chromatography gave light yellow foam L3 (2.12g, 23.4%).
[0068]
[0069] 1 HNMR (CDCl 3 ,400MHz,298K):δ9.79(s,1H,OH),7.34–7.11(m,19H,ArH),6.97-6.95(m,2H,ArH),6.79(d,1H, 4 J=2.0Hz, ArH), 5.15 (pesudot, 1H, 3 J=9.2Hz,CH 2 O),4.53(dd,1H, 3 J=8.4Hz, 2 J=10.4Hz,CH 2 O),4.02(t,1H, 3 J=8.4Hz, CHN), 3.84(s, 2H, ArCH 2 ),3.55(d,2H, 4 J=1.6Hz, PhCH 2 ),3.27(s,2H,NCH 2 C=N),1.69(s,12H,PhC(CH 3 ) 2 ). 13 CNMR (CDCl 3 ,100MHz,298K):δ165.0,153.6,151.6,151.5,142.0,140.2,136.8,135.5,130.0,128.8,128.5,128.0,127.8,127.6,127.5,126.9,126.6,126.5,125.5,125.8 121.5, 74.5, 69.5, 58.5, 56.5, ...
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