With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29841-69-8,(1S,2S)-(-)-1,2-Diphenylethylenediamine,as a common compound, the synthetic route is as follows.
In a single-necked 50 mL round-bottom flask bis-aldehyde c (0.72 g, 1.5 mmol) was taken in dry MeOH (10 mL) and was stirred at 0 C, and a solution of 1S,2S-(+)-1,2-diaminocyclohexane (0.18 g,1.6 mmol)/1S, 2S-(-)-1,2-diphenylethane-1,2-diamine (0.34 g,1.6 mmol) in dry MeOH (5 mL) was added drop wise to the above solution. After complete addition, the resulting solution was further stirred at room temperature. After an interval of 12 h, solvent was completely removed under reduced pressure, and the bright yellow solid was extracted with dichloromethane (50 mL). The organic layer was washed with water (3 ¡Á 50 mL) and with brine (3 ¡Á 50 mL) and finally dried over anhydrous Na2SO4. After removal of dichloromethane under reduced pressure, the chiral ligands 1′ and 2′ purified by silica gel column chromatography (100-200 mesh) in 20% (EtOAc: Hexane) resulted in yellowish solid monomeric macrocyclic ligands, 1′ and 2′.1′: Yield 85%. m.p. 104 C. 1H NMR (500 MHz, CDCl3): delta 1.44 (18 H, s), 1.73-1.91 (8H, m), 3.23-3.25 (2H, m), 3.31-3.33 (4H, m), 3.51-3.62 (8H, m), 4.19 (2H, d, J = 11), 4.43 (2H, d, J = 11), 6.72 (2H, s), 7.27 (2H, s), 8.07 (2H, s), 11.78 (2H, br) ppm. 13C NMR (125 MHz, CDCl3): 24.3, 29.4, 32.7, 34.8, 68.5, 69.2, 70.7, 72.3, 76.4, 118.3, 127.3, 129.8, 137.4, 160.0, 166.2 ppm. FT-IR (KBr): nu 3432, 2942, 2863, 2359, 1629, 1558, 1442, 1387, 1259, 1212, 1099, 970, 845, 768, 728, 668, 594 cm-1. (c = 0.052, CH2Cl2). Anal. Calcd. for C36H52N2O6: C, 71.02; H, 8.61; N, 4.60. Found C, 71.0; H, 8.58; N, 4.58. TOF-MS (ESI+): m/z Calcd. for [C36H52N2O6] 608.81, Found 610.2 [M+H].2′: Yield 90%. m.p. 98 C. 1H NMR (200 MHz, CDCl3): delta 1.46 (18H, s), 3.30-3.36 (4H, m), 3.57-3.68 (8H, m), 4.19 (2H, d, J = 10), 4.47 (2H, d, J = 10), 4.56 (2H, s), 6.72 (2H, d, J = 1.8), 7.18-7.30 (12H, m), 8.24 (2H, s), 13.86 (2H, br) ppm. 13C NMR (50 MHz, CDCl3): 29.5, 33.9, 69.0, 70.8, 72.5, 78.6, 118.3, 127.5, 128.3, 128.4, 129.2, 137.4, 139.8, 160.1, 166.8 ppm. IR (KBr): nu 3452, 2929, 2865, 1626, 1553, 1440, 1263, 1096, 848, 726, 585, 464 cm-1. (c = 0.206, CHCl3). Anal. Calcd. for C44H54N2O6 C, 74.76; H, 7.70; N, 3.96. Found C, 74.73; H, 7.68; N, 3.93. TOF-MS (ESI+): m/z Calcd. for [C44H54N2O6] 706.91, Found 708.45 [M+H].
As the paragraph descriping shows that 29841-69-8 is playing an increasingly important role.
Reference£º
Article; Kureshy, Rukhsana I.; Roy, Tamal; Khan, Noor-Ul H.; Abdi, Sayed H.R.; Sadhukhan, Arghya; Bajaj, Hari C.; Journal of Catalysis; vol. 286; (2012); p. 41 – 50;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI