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: 4.24.12 N-(3,5-Ditrifluoromethyl)benzyl-6′-hydroxyquinidi-nium bromide (4c) Ethanethiol (2.30 mL, 30.8 mmol) was added under argon atmosphere to a stirred suspension of sodium hydride (370.0 mg, 15.4 mmol) in dry DMF (15 mL). Quinidine (500 mg, 1.5 mmol) in dry DMF (7.5 mL) was added dropwise and the reaction mixture was stirred at 110 C for 13 h. The solvent and excess ethanethiol were removed under reduced pressure. Then the 3,5-ditrifluoromethylbenzyl bromide (675.4 mg, 2.2 mmol) was added in THF (9 mL). The reaction mixture was refluxed and monitored by TLC analysis. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (MeOH/EtOAc = 1/20, V/V). Yield 52%; white solid; mp 258 C (decomp.); [alpha]D28 +182.3 (c 0.16, CH3OH); IR (KBr): 3369, 3234, 1622, 1531, 1469, 1217, 1181, 1135, 1003, 927, 905, 864, 842, 736, 709, 683 cm-1; 1H NMR (400 MHz, DMSO-d6): delta = 10.06 (s, 1H), 8.75 (d, J = 4.4 Hz, 1H), 8.63 (s, 2H), 8.37 (s, 1H), 7.95 (d, J = 8.8 Hz, 1H), 7.70 (d, J = 4.4 Hz, 1H), 7.67 (d, J = 2.4 Hz, 1H), 7.38 (dd, J = 9.0, 2.2 Hz, 1H), 6.68 (d, J = 3.6 Hz, 1H), 6.32 (s, 1H), 6.02 (ddd, J = 17.4, 10.5, 6.9 Hz, 1H), 5.38 (d, J = 12.4 Hz, 1H), 5.26-5.19 (m, 3H), 4.32 (t, J = 9.6 Hz, 1H), 4.13 (t, J = 9.6 Hz, 1H), 3.92 (t, J = 9.6 Hz, 1H), 3.49 (t, J = 11.2 Hz, 1H), 3.12-3.05 (m, 1H), 2.65-2.59 (m, 1H), 2.33 (t, J = 11.6 Hz, 1H), 1.89 (s, 1H), 1.83-1.78 (m, 2H), 1.17-1.09 (m, 1H); 13C NMR (100 MHz, DMSO-d6): delta = 156.5, 147.2, 143.4, 143.1, 137.7, 135.2, 131.9, 131.7, 131.2 (q, J = 33.0 Hz), 126.1, 124.6 (q, J = 3.2 Hz), 123.7 (q, J = 271.8 Hz), 122.2, 120.4, 117.6, 105.1, 68.2, 65.3, 60.9, 56.3, 54.7, 37.3, 26.9, 23.6, 21.0; HRMS calcd for [C28H27F6N2O2]+: 537.1971, found 537.1959.
56-54-2 (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol 637552, acatalyst-ligand compound, is more and more widely used in various.
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