Tag: 4488-22-6

4488-22-6, [1,1′-Binaphthalene]-2,2′-diamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a two-necked round-bottomed flask (50 mL) equipped with a magnetic stir bar, was added biaryldiamine 1 (or 3) (0.1 mmol) under the air. The flask was capped with a rubber septum, evacuated, and refilled with N2 gas for three times. Solvent (10 mL) and 2,6-lutidine (23.5 mg, 0.22 mmol or none) were added to the tube through the septum. To the mixture, was added t-BuOCl (23.8 mg, 0.22 mmol or 43.4 mg, 0.40 mmol) through the septum at the indicated temperature. The resulting solution was stirred for the indicated time (Table 2 in the text) before quenched with aqueous Na2S2O3 solution (1.0 M, 20 mL), and the resulting mixture was extracted with CH2Cl2 (20 mL ¡Á 3). The combined organic extracts were dried over Na2SO4 and concentrated under vacuum to give the crude product. Purification by flash column chromatography on silica gel gave the corresponding 7,8-diaza[5]helicene (for example, compound 2a: 27.2 mg, 97%).

As the paragraph descriping shows that 4488-22-6 is playing an increasingly important role.

Reference£º
Article; Takeda, Youhei; Okazaki, Masato; Maruoka, Yoshiaki; Minakata, Satoshi; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 9 – 15;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4488-22-6,[1,1′-Binaphthalene]-2,2′-diamine,as a common compound, the synthetic route is as follows.

General procedure: In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), triphenylphosphine (13.2 mg, 0.05 mmol), 17-iodo-5alpha-androsta-16-ene 1 (0.5 mmol), 2,2′-diamino-1,1′-binaphthalene 2 (varied from 1.0 mmol to 0.125 mmol) and triethylamine (0.5 mL) were dissolved in DMF (10 mL) under argon in a 100 mL three-necked flask equipped with a gas inlet, reflux condenser with a balloon (filled with argon) at the top. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50 C and analysed by TLC. The mixture was then concentrated and evaporated to dryness. The residue was dissolved in chloroform (20 mL) and washed with water (3 20 mL), 5% hydrochloric acid (20 mL), saturated NaHCO3 (20 mL) and brine (20 mL). The organic phase was dried over Na2SO4, filtered and evaporated to give a solid material. All compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200 mm), EtOAc/CHCl3 or hexane/CHCl3 (the exact ratios are specified in Section 4.4 for each compound). 4.3. Characterisation of the products (Fig. 3) (Sax)-3: Yield: 410 mg (72%). Off-white yellow solid, mp 137-142 C; [Found: C, 84.55; H, 7.65; N, 4.70; C40H44N2O requires C,84.46; H, 7.80; N, 4.93]; Rf (5% EtOAc/CHCl3) 0.68. 1H NMR (CDCl3) delta: 8.94 (1H, d, 9.0 Hz, H-30), 8.03 (1H, d, 9.0 Hz, H-40), 7.94 (1H, d,8.2 Hz, H-50), 7.87 (1H, d, 8.5 Hz, H-300), 7.82 (1H, d, 7.5 Hz, H-400), 7.43 (1H, dt, 6.3 Hz, 1.6 Hz, H-60), 7.35 (1H, s, NH), 7.31 (1H, dt,8.5 Hz, 0.8 Hz, H-70), 7.29-7.26 (2H, m, H-600 , H-600), 7.23 (1H, dt,6.8 Hz, 1.1 Hz, H-700), 7.16 (1H, d, 8.7 Hz, H-80), 6.96 (1H, d, 8.2 Hz,H-800), 6.21 (1H, dd, 2.9 Hz, 1.5 Hz, H-16), 3.69 (2H, s, NH2), 2.05 (1H, ddd, 16.7 Hz, 6.5 Hz, 3.4 Hz, 15-CHaHb), 1.78 (1H, ddd,16.7 Hz, 11.9 Hz, 1.4 Hz, 15-CHaHb), 1.07-0.54 (23H, m, skeleton protons), 0.78 (3H, s, 19-CH3), 0.62 (3H, s, 18-CH3). 13C NMR (CDCl3) delta: 163.6, 150.4, 143.0, 140.0, 135.7, 133.8, 132.5. 131.1, 130.3, 129.3, 128.3, 128.2, 128.1, 127.5, 126.8, 125.3, 124.9, 123.6, 122.8, 120.4, 119.7, 118.1, 110.5, 56.8, 54.7, 47.2, 45.3, 38.4, 36.3, 34.2, 33.7, 31.8, 31.4, 29.0, 28.8, 26.8, 22.2, 20.5, 16.0, 12.1. IR (KBr, m(cm1)): 3440 (amide-NH), 3398 (NH2), 1665 (CON), 1620 (CC). MS m/z (rel int.): 569.4 (100, (M+H)+), 381 (9), MS/MS m/z (relint.): 551.4 (29), 285.2 (100). [alpha]D20 = 37.1 (c 1.34, CHCl3). (Rax)-3: Yield: 114 mg (20%). Off-white solid substance; [Found:C, 84.30; H, 7.66; N, 4.77; C40H44N2O requires C, 84.46; H, 7.80; N,4.93]; Rf (5% EtOAc/CHCl3) 0.72. 1H NMR (CDCl3) delta: 8.95 (1H, d,9.0 Hz, H-30), 8.03 (1H, d, 9.0 Hz, H-40), 7.93 (1H, d, 7.9 Hz, H-50), 7.87 (1H, d, 8.9 Hz, H-300), 7.82 (1H, d, 7.8 Hz, H-400), 7.43 (1H, dt,6.4 Hz, 1.2 Hz, H-60), 7.36 (1H, s, NH), 7.31 (1H, dt, 8.6 Hz, 0.8 Hz,H-70), 7.29-7.26 (2H, m, H-6”, H”), 7.23 (1H, dt, 6.9 Hz, 1.5 Hz,H-7”), 7.16 (1H, d, 8.5 Hz, H-8′), 6.96 (1H, d, 8.4 Hz, H-8”), 6.21 (1H, dd, 3.1 Hz, 1.5 Hz, H-16), 3.69 (2H, s, NH2), 2.05 (1H, ddd, 16.3 Hz, 6.4 Hz, 3.4 Hz, 15-CHaHb), 1.78 (1H, ddd, 16.6 Hz,11.7 Hz, 2.0 Hz, 15-CHaHb), 1.07-0.53 (23H, m, skeleton protons), 0.77 (3H, s, 19-CH3), 0.31 (3H, s, 18-CH3). 13C NMR (CDCl3) delta: 163.5, 150.4, 143.1, 140.2, 135.7, 133.8, 132.4, 131.1, 130.3, 129.3, 128.4, 128.3, 128.2, 127.5, 126.8, 125.3, 124.9, 123.6,122.8, 120.4, 119.7, 118.0, 110.6, 56.8, 54.8, 47.2, 45.2, 38.4, 36.3, 34.2, 33.7, 31.7, 31.4, 29.0, 28.8, 26.8, 22.2, 20.5, 15.5, 12.1. IR(KBr, m (cm1)): 3441 (amide-NH), 3396 (NH2), 1665 (CON), 1620 (CC). MS m/z (rel int.): 569.4 (100, (M+H)+), 381 (9), MS/MS m/z (rel int.): 551.4 (29), 285.2 (100). [alpha]D20 = +191.5 (c 0.914, CHCl3). (Sax)-4: Yield: 102 mg (12%). Beige solid substance; [Found: C,84.31; H, 8.35; N, 3.12; C60H72N2O2 requires C, 84.45; H, 8.51; N,3.28]; Rf (10% hexane/CHCl3) 0.69. 1H NMR (CDCl3) alpha: 8.94 (2H, d,9.2 Hz, H-3′), 8.08 (2H, d, 9.2 Hz, H-4′), 7.95 (2H, d, 8.2 Hz, H-5′),7.46 (2H, dt, 7.2 Hz, 0.9 Hz, H-6′), 7.35 (2H, dt, 7.2 Hz, 0.9 Hz, H-7′), 7.1 (2H, d, 9.3 Hz, H-8′), 7.13 (2H, s, NH), 6.05 (2H, dd, 3.1 Hz, 1.5 Hz, H-16), 2.02 (2H, ddd, 16.8 Hz, 6.4 Hz, 3.1 Hz, 15-CHaHb), 1.88 (2H, dd, 9.9 Hz, 3.1 Hz, 14-CH), 1.75 (2H, ddd, 16.8 Hz,11.7 Hz, 1.5 Hz, 15-CHaHb), 1.69-0.54 (44H, m, skeleton protons), 0.77 (6H, s, 19-CH3), 0.57 (6H, s, 18-CH3). 13C NMR (CDCl3) alpha: 163.6, 150.2, 140.0, 136.0, 135.2, 132.4, 131.3, 130.0, 128.2,127.5, 125.3, 124.9, 120.5, 118.1, 56.6, 54.8, 47.2, 45.4, 38.4, 36.3, 34.2, 33.6, 31.7, 31.4, 29.0, 28.8, 26.8, 22.1, 20.5, 16.1, 12.1. IR (KBr, m (cm1)): 3408 (amide-NH), 1677 (CON), 1621 (CC). MS m/z (rel int.): 853.6 ((M+H)+); 875.6 ((M+Na)+), 891.5 ((M+K)+). [alpha]D20 = +12.0 (c 0.418, CHCl3). (Rax)-4: Yield: 85 mg (10%). Beige solid substance; [Found: C,84.28; H, 8.30; N, 3.06; C60H72N2O2 requires C, 84.45; H, 8.51; N,3.28]; Rf (10% hexane/CHCl3) 0.74. 1H NMR (CDCl3) alpha: 8.95 (2H, d,9.0 Hz, H-3′), 8.08 (2H, d, 9.0 Hz, H-4′), 7.96 (2H, d, 7.8 Hz, H-5′), 7.46 (2H, dt, 7.8 Hz, 0.9 Hz, H-6’…

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Reference£º
Article; Mikle, Gbor; Boros, Borbla; Kollr, Lszl; Tetrahedron Asymmetry; vol. 25; 23; (2014); p. 1527 – 1531;,
Chiral Catalysts
Chiral catalysts – SlideShare