Chiral ligand with acetylacetone derivative as well as preparation method and application of chiral ligand
A technology of acetylacetone and chiral ligands, which is applied in the field of divalent nitrogen-oxygen chiral ligands and its preparation, can solve the problems of polluting the ecological environment, rapid development constraints, slow degradation, etc., and achieve high catalytic activity, good performance, The effect of high stereoselectivity
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Embodiment 1
[0049] The structural formula of the synthesized ligand is the above formula (A), where R 1 is methyl; R 2 is methyl, the reaction process is: add 0.25 g of unilaterally protected chiral cyclohexanediamine (a) and equimolar amount of acetylacetone into 20 mL of methanol, heat and reflux for 10 hours, cool and filter after the reaction, and use cold washed with methanol, filtered, collected, dried and weighed to obtain 0.29 g of solid, with a yield of 87.9%.
[0050] The NMR information of the obtained product is as follows, as can be seen from the NMR information, R 1 is methyl; R 2 The ligand for the methyl group was successfully synthesized.
[0051] 1 H NMR (400 MHz, CDCl 3 ) δ 11.10 (s, 1H, O H ), 8.13 (d, J = 7.0Hz, 2H,Ar– H ), 7.62 (d, J = 7.0 Hz, 2H, Ar– H ), 5.26 (s, 1H, C H ), 4.32 (m, 1H, NC H ),3.45 (m, 1H, =NC H ), 2.54 (m, 1H, C H 2 ), 2.10 (s, 6H, C H 3 ), 2.00 (m, 5H, C H 2 ),1.52 (m, 2H, C H 2 ). HRESI-MS: m / z ccld. C 19 h 22 N 2 o ...
Embodiment 2
[0053] The structural formula of the synthesized ligand is the above formula (A), where R 1 is methyl; R 2 is trifluoromethyl, the reaction process is: add 0.30 g of unilaterally protected chiral cyclohexanediamine (a) and an equimolar amount of trifluoroacetylacetone into 20 mL of methanol, heat and reflux for 12 hours, after the reaction Cool and filter and wash with cold methanol, filter, collect, dry and weigh to obtain 0.38 g of solid, with a yield of 80.9%.
[0054] The NMR information of the obtained product is as follows, as can be seen from the NMR information, R 1 is methyl; R 2 The ligand for trifluoromethyl was synthesized successfully.
[0055] 1 H NMR (400 MHz, CDCl 3 ) δ 11.03 (s, 1H, O H ), 8.17 (d, J = 7.2 Hz, 2H,Ar– H ), 7.52 (d, J = 7.2 Hz, 2H, Ar– H ), 5.70 (s, 1H, C H ), 4.33 (m, 1H, NC H ),3.45 (m, 1H, =NC H ), 2.58 (m, 1H, C H 2 ), 2.12 (s, 3H, C H 3 ), 2.04 (m, 5H, C H 2 ),1.61 (m, 2H, C H 2 ). HRESI-MS: m / z cacld.C 19 h 19 f...
Embodiment 3
[0057] The structural formula of the synthesized ligand is the above formula (A), where R 1 is trifluoromethyl; R 2 is a phenyl group, the reaction process is: add 0.20 g of unilaterally protected chiral cyclohexanediamine (a) and an equimolar amount of benzoyltrifluoroacetone to 10 mL of methanol, heat and reflux for 8 hours, and after the reaction Cool and filter and wash with cold methanol, filter, collect, dry and weigh to obtain 0.29 g of solid, with a yield of 80.6%.
[0058] The NMR information of the obtained product is as follows, as can be seen from the NMR information, R 1 is trifluoromethyl; R 2 The ligand for phenyl was synthesized successfully.
[0059] 1 H NMR (400 MHz, CDCl 3 ) δ 12.74 (s, 1H, O H ), 8.08 (d, J = 7.0 Hz, 2H,Ar– H ), 7.53 (d, J = 7.0 Hz, 2H, Ar– H), 7.42(m, 3H, Ar– H), 7.17 (d, J = 6.2Hz, 2H, Ar– H ), 6.52 (s, 1H, C H ), 4.48 (m, 1H, NC H ), 3.92 (m, 1H, =NC H 2 ), 2.57(m, 1H, C H 2 ), 2.10 (m, 5H, C H 2 ), 1.54 (m, 2H...
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