Category: 4488-22-6

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’…

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

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

4488-22-6, The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

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

Name is [1,1′-Binaphthalene]-2,2′-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 4488-22-6, its synthesis route is as follows.,4488-22-6

To a solution of 1,1?binaphthyl-2,2?-diamine 2 (569 mg, 2 mmol) in THF (30 mL) was added solid Na2CO3 (212 mg, 2 mmol) followed by dropwise addition of TFAA (1.27 mL, 9 mmol) in THF (30 mL). After 2 h the reaction was quenched with sat. NaHCO3 solution an

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine

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.

To a solution of 1,1?binaphthyl-2,2?-diamine 2 (569 mg, 2 mmol) in THF (30 mL) was added solid Na2CO3 (212 mg, 2 mmol) followed by dropwise addition of TFAA (1.27 mL, 9 mmol) in THF (30 mL). After 2 h the reaction was quenched with sat. NaHCO3 solution and extracted with EtOAc, washed with H2O and brine, dried (Na2SO4), and evaporated to give 826 mg (87%) of 3c; colorless crystals; m.p.: 195-196 C. The product was pure enough for the next step. 1H-NMR: delta = 8.19 (d, J = 8.9 Hz, 2H); 8.14 (d, J = 8.9 Hz, 2H); 8.01 (d, J = 8.2 Hz, 2H); 7.72 (s, 2H); 7.56 (ddd, J = 8.2, 6.8, 1.2 Hz, 2H); 7.38 (ddd, J = 8.4, 6.8, 1.3 Hz, 2H); 7.13 (dm, J = 8.6 Hz, 2H). 13C-NMR delta = 132.3 (C); 131.8 (C); 131.7 (C); 130.9 (CH); 128.7 (CH); 128.2 (CH); 127.0 (CH); 124.7 (CH); 124.0 (C); 121.8 (CH); 115.3 (CF3, JCF ~280 Hz). HRMS: calcd for C24H15F6N2O2 [M + H]+: 477.1038; found 477.1041., 4488-22-6

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

Reference£º
Article; Lemmerer, Miran; Abraham, Michael; Brutiu, Bogdan R.; Roller, Alexander; Widhalm, Michael; Molecules; vol. 24; 17; (2019);,
Chiral Catalysts
Chiral catalysts – SlideShare

[1,1′-Binaphthalene]-2,2′-diamine, cas is 4488-22-6, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,4488-22-6

To a solution of 2 (142 mg, 0.5 mmol) in pyridine (1 mL)/DCM (4 mL) was added mesylchloride (126 mg, 1.1 mmol) and the orange mixture was stirred at r.t. After 24 h, a second portion of mesylchloride was added (126 mg, 1.1 mmol) and stirring was continued. After complete conversion (TLC), the reaction was acidified (HCl, 1 M) and sufficiently extracted with DCM. The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. The crude mixture was purified by MPLC (EtOAc (30?50%)/heptane) to yield 223 mg (quant.) of 3a as a mixture of tautomers; m.p.: 221-222 C. 1H-NMR (C2-symmetric tautomer) delta = 8.10 (d, J = 8.9 Hz, 2H); 8.02 (d, J = 8.9 Hz, 2H); 7.95 (br.d, J = 8.2 Hz, 2H); 7.47 (ddd, J =8.0, 6.8, 1.1 Hz, 2H); 7.31 (ddd, J = 8.4, 6.9, 1.3 Hz, 2H); 6.99 (br.d, J = 8.3 Hz, 2H); 6.02 (br.s, 2H); 2.97 (s, 6H). 13C-NMR delta = 134.4 (C); 132.5 (C); 131.5 (CH); 131.2 (C); 128.7 (CH); 128.2 (CH); 126.1 (CH); 124.5 (CH); 118.5 (C); 118.2 (CH); 41.0 (CH3). HRMS: calcd for C22H20NaN2O4S2 [M + Na]+: 463.0762; found 463.0762.

4488-22-6 is used more and more widely, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine

Reference£º
Article; Lemmerer, Miran; Abraham, Michael; Brutiu, Bogdan R.; Roller, Alexander; Widhalm, Michael; Molecules; vol. 24; 17; (2019);,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is [1,1′-Binaphthalene]-2,2′-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 4488-22-6, its synthesis route is as follows.,4488-22-6

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’…

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine

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

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: 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’…, 4488-22-6

The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

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

Name is [1,1′-Binaphthalene]-2,2′-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 4488-22-6, its synthesis route is as follows.,4488-22-6

To a solution of BINAM (148 mg, 0. 5 mmol) in THF (anhydrous, 10 mL) was added dropwise 2.5 M n-BuLi in cyclohexane (0.56 mL, 1.4 mmol) at -40oC over 40 min and the reaction mixture was stirred for 1 h. The chlorodiphenylphosphine (440 mg, 1.8 mmol) was added and the reaction was stirred for a further 10 h at -40oC to room temperature. Then, the reaction was quenched with saturated sodium bicarbonate and the mixture was dissolved in little water and extracted with EtOAc (15 mL ¡Á 3). The combined organic extracts were dried (MgSO4)and concentrated. The residue was purified by column chromatography on silica gel using PE-EtOAc as the eluent, to give A-3; yield: 255 mg (67%);

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine

Reference£º
Article; Zhang, Yu; Mao, Mao; Ji, Yi-Gang; Zhu, Jie; Wu, Lei; Tetrahedron Letters; vol. 57; 3; (2016); p. 329 – 332;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is [1,1′-Binaphthalene]-2,2′-diamine, and cas is 4488-22-6, its synthesis route is as follows.,4488-22-6

EXAMPLE 1 Preparation of (R)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl-2,2′-diamine (R-1): 200 mg (R)-1,1′-binaphthyl-2,2′-diamine (purchased from Aldrich Chemical Company), 20 mg PtO2 and 20 mL glacial acetic acid were charged into a 50 mL autoclave equipped with a magnetic stirring bar. The autoclave was closed and 1,000 KPa hydrogen gas was charged. The solution was stirred with a magnetic stirrer for 120 hours at room temperature. After releasing the hydrogen gas and removing the solid catalyst by filtration, the mixture was neutralized with aqueous NaHCO3 solution followed by extraction with 50 mL ethyl acetate three times. The combined extracts were dried with sodium sulfate and the solvent was removed with a rotary evaporator to give 210 mg of crude product (R-1). The crude product was purified by crystallization with 5 mL ethyl acetate and 15 mL hexane to give 180 mg crystals of R-1 (87.5% of theoretical yield).

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine,belong chiral-catalyst compound

Reference£º
Patent; The Hong Kong Polytechnic University; US5919981; (1999); A;,
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.

Preparation of ligands.; Synthesis of imines.; 3 mmol of bisnaphthyldiamine and 6 mmol of ketone were dissolved in 30 mL of anhydrous toluene. A few mg of para toluene sulfonic acid were added. After addition of 30 g of activated 4 angstroem molecular sieves by 10 g portions, the reaction mixture was stirred at a temperature of 110C for a period of time of 3 days. Molecular sieves were filtered off and the solvent was removed under vacuum. The resulting solid was crystallised from methanol to give the product. Two compounds were obtained and characterised. Bis-naphthyldi(phenylmethyleneimine) was obtained as a yellow solid with a yield of 79 %. [Show Image] The NMR results were as follows. 1H-RMN (300 MHz, CD2Cl2) [Show Image] (ppm) : 6.64 (d, 2H), 6.7-4-78 (m, 8H), 6.93-6.97 (m, 4H), 7.05 (t, 2H), 7.19-7.48 (m, 6H), 7.50 (t, 2H), 7.68 (d, 6H), 7.77 (d, 2H) 13C-RMN (75 MHz, CD2Cl2) [Show Image] (ppm) : 122.2, 124.1, 124.2, 126.1, 126.5, 127.8, 127.9, 128.0, 128.2, 128.3, 128.9, 130.0, 130.2, 130.6, 130.7, 133.9, 136.6, 140.8, 147.6, 167.2

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

Reference£º
Patent; TOTAL PETROCHEMICALS RESEARCH FELUY; EP1982975; (2008); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare