17261-28-8, 2-(Diphenylphosphino)benzoic acid is a chiral-phosphine-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
To a solution of (1R,5S)-(?)-cytisine (571mg, 3.00mmol) in CH3OH (10mL) was added platinum (IV) oxide hydrate (80percent Pt) (82mg, 0.30mmol) and the mixture was stirred at room temperature under a hydrogen atmosphere (balloon) for 48h. The solids were removed by filtration through Celite and the filter cake was washed with CH2Cl2/CH3OH (9:1). The filtrate was evaporated under reduced pressure to give the crude product. Purification by flash column chromatography (silica gel, CH2Cl2/CH3OH/Et3N=20:1:0.5) gave lactam 4 (314mg, 54percent) as a white solid [8b]. To a mixture of 2-diphenylphosphinobenzoic acid (76mg, 0.25mmol), N-[3-(dimethylamino)propyl]-N-ethylcarbodiimide (58mg, 0.30mmol) and hydroxybenzotriazole (41mg, 0.30mmol) in dry CH2Cl2 (5mL) under an argon atmosphere lactam 4 (63mg, 0.32mmol) was added at room temperature. The mixture was stirred at room temperature for 24h and then was directly subjected to flash column chromatography (silica gel, CH2Cl2/CH3OH=50:1) to give 116mg (97percent yield) of 5 as a white solid; m.p. 194?196¡ãC. [alpha]D20=?18.2 (c 0.31, CHCl3). 1H NMR (600MHz, CDCl3, 293K): delta=7.42 (t, JH,H=7.4Hz, 1H, Har), 7.35?7.30 (m, 6H, Har), 7.29?7.28 (m, 3H, Har), 7.25 (dt, JH,H=7.7Hz, 1H, Har), 7.23?7.21 (m, 2H, Har), 7.02 (dd, JH,H=7.3, 4.0Hz, 1H, Har), 5.06 (d, JH,H=13.9Hz, 1H, 2-Heq), 4.60 (d, JH,H=13.8Hz, 1H, 4-Heq), 3.50?3.46 (m, 1H, 12-H), 3.44 (d, JH,H=12.5Hz, 1H, 6-H), 2.98 (d, JH,H=12.5Hz, 1H, 6-H), 2.81 (d, JH,H=14.0Hz, 1H, 4-Hax), 2.78 (d, JH,H=14.0Hz, 1H, 2-Hax), 2.52?2.43 (m, 2H, 9-H, 10-H), 2.22 (dq, JH,H=13.0, 3.0Hz, 1H, 11-H), 1.96?1.85 (m, 4H, 9-H, 10-H, 11-H, 13-H), 1.80 (brs, 2H, 1-H, 5-H), 1.70?1.63 (m, 1H, 13-H) ppm. 13C NMR (150.9MHz, CDCl3, 293K): delta=170.32 (Cq, C=O, lactam), 170.12 (Cq, C=O, amide), 142.65 (d, J31P,13C=32.6Hz, Cq, Car), 136.55 (d, J31P,13C=9.9Hz, Cq, Car), 136.14 (d, J31P,13C=10.1Hz, Cq, Car), 133.99 (d J31P,13C=20.3Hz, 2 CH, Car), 133.73 (CH, Car), 133.28 (d, J31P,13C=19.6Hz, 2 CH, Car), 131.67 (Cq, CCO), 129.79 (CH, Car), 128.82 (CH, Car), 128.70 (CH, Car), 128.50 (CH, Car), 128.49 (d, J31P,13C=6.5Hz, 2 CH, Car), 128.32 (d, J31P,13C=6.9Hz, 2 CH, Car), 127.52 (d, J31P,13C=7.1Hz, CH, Car), 59.53 (CH, 12-C), 51.80 (CH2, 6-C), 45.72 (CH2, 4-C), 41.63 (CH2, 2-C), 33.02 (2 CH2, 9-C, 10-C), 32.70 (CH, 1-C), 28.15 (CH, 5-C), 28.10 (CH2, 11-C), 20.16 (CH2, 13-C) ppm. 31P{1H} NMR (242.92MHz, CDCl3, 293K): delta=?12.20ppm. IR(KBr): nu=3058, 2922, 2861, 1624, 1584, 1439, 1422, 1254, 1182, 779, 692cm?1. MS (ESI): m/z=483 (100, [M+1]+), 289 (52). C30H31N2O2P (482.55): calcd. C 74.67, H 6.48, N 5.81, found C 74.58, H 6.71, N 5.89., 17261-28-8
As the paragraph descriping shows that 17261-28-8 is playing an increasingly important role.
Reference£º
Article; Philipova, Irena; Stavrakov, Georgi; Vassilev, Nikolay; Nikolova, Rositsa; Shivachev, Boris; Dimitrov, Vladimir; Journal of Organometallic Chemistry; vol. 778; (2015); p. 10 – 20;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate