56-54-2, (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
56-54-2, General procedure: To a flame-dried flask equipped with a magnetic stirring bar and a condenser was added with cinchona alkaloids (1 mmol), toluene (5 mL), and benzyl bromide derivatives (1.2 mmol, 1.2 equiv.). The mixture was heated at 80 8C until a TLC analysis showing that the starting material was completely consumed. Cooled to room temperature and poured onto Et2O (30 mL) with stirring, the resulting suspension was stirred for another 1 h. Then the precipitate was purified by flash chromatography (MeOH/EtOAc = 1/10, V/V). 4.24.4 N-(2-F-4-Br-benzyl)quinidinium bromide (1d) Yield: 79%; white solid; m.p. 174-176 C (decomp.); [alpha]D28 +143.3 (c 0.14, CH3OH); IR (KBr): 3387, 3198, 3006, 1621, 1520, 1473, 1460, 1431, 1338, 1259, 1241, 1205, 1113, 1026, 851, 828, 719 cm-1; 1H NMR (400 MHz, DMSO-d6): delta = 8.81 (d, J = 4.4 Hz, 1H), 8.02 (d, J = 9.2 Hz, 1H), 7.87-7.76 (m, 3H), 7.67 (dd, J = 8.4, 1.6 Hz, 1H), 7.50 (dd, J = 9.2, 2.0 Hz, 1H), 7.41 (d, J = 2.4 Hz, 1H), 6.86 (d, J = 2.8 Hz, 1H), 6.51 (s, 1H), 6.03 (ddd, J = 17.2, 10.4, 6.8 Hz, 1H), 5.25-5.23 (m, 2H), 5.06 (d, J = 12.4 Hz, 1H), 4.77 (d, J = 12.4 Hz, 1H), 4.19 (t, J = 9.6 Hz, 1H), 4.06 (s, 3H), 3.97-3.85 (m, 2H), 3.44 (t, J = 11.2 Hz, 1H), 3.12 (q, J = 10.0 Hz, 1H), 2.68-2.62 (m,1H), 2.36 (t, J = 11.2 Hz, 1H), 2.00 (s, 1H), 1.82-1.75 (m, 2H), 1.10-1.03 (m, 1H); 13C NMR (100 MHz, DMSO-d6): delta = 162.1 (d, J = 252.2 Hz), 157.9, 147.9, 144.2, 143.8, 137.6, 131.9, 129.0, 125.8, 125.5 (d, J = 10.1 Hz), 121.9, 120.7, 120.3 (d, J = 25.7 Hz), 117.5, 115.4 (d, J = 13.7 Hz), 102.8, 67.9, 65.3, 56.8, 56.1, 54.7, 37.4, 26.6, 23.7, 21.0; HRMS calcd for [C33H35F6N2O2]+: 511.1391, found 511.1398.
The synthetic route of 56-54-2 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Wu, Shaoxiang; Guo, Jiyi; Sohail, Muhammad; Cao, Chengyao; Chen, Fu-Xue; Journal of Fluorine Chemistry; vol. 148; (2013); p. 19 – 29;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI