Category: 4488-22-6

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO348,mainly used in chemical industry, its synthesis route is as follows.,4488-22-6

Under nitrogen conditions, add tris (dibenzylidene-base acetone) dipalladium (37 mg, 0.04 mmol, purchased from ANEG) to Schlenk bottles with magnetons, 1,1′-Binaphthyl-2,2′-bisdiphenylphosphine (50 mg, 0.08 mmol, purchased from Anagi), cesium carbonate (3.65 g, 11.2 mmol, purchased from Anagi), 2-trifluoromethanesulfonyl cycloheptatrienone (4.88 g, 19.2 mmol), 1,1′-bi-2-naphthylamine (2.27 g, 8 mmol, purchased from Enagi) and 50 ml of toluene. The resulting mixture was stirred at 100 C for 24 hours. The reaction was completed and the temperature was reduced to room temperature. After the toluene-insoluble solid was filtered off with diatomaceous earth, 100 mesh silica gel was added to the resulting solution to spin dry the sample. The obtained crude product was then passed through a 200-300 mesh silica gel column, using ethyl acetate as an eluent, and the eluent was spin-dried to obtain a brown solid (2.68 g, yield 68%).

With the synthetic route has been constantly updated, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine,belong chiral-catalyst compound

Reference£º
Patent; University of Science and Technology of China; Chen Changle; Zhang Pan; (17 pag.)CN110423246; (2019); A;,
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

The mixture of BINAM (227.2 mg, 0.8 mmol), BoC-D-proline (222.9 mg, 0.73 mmol), EDCI (95.8 mg, 1.45 mmol) and HOBt (196 mg, 1.45 mmol) in DCM (20 mL) was tirred at room temperature for 5 h. The mixture was washed by water (25 mL ¡Á 3), dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel using PE-EtOAc as the eluent, to give tert-butyl2-((2′-amino-[1,1′-binaphthalen]-2-yl)carbamoyl)pyrrolidine-1-carboxylate; yield: 202 mg (54%). Then 1.5 ml TFA and 1.5 ml Et3SiH were added to the prepared tert-butyl2-((2′-amino-[1,1′-binaphthalen]-2-yl)carbamoyl)pyrrolidine-1-carboxylate in DCM (2.0 mL) , after stirred for 2 h the residue was added NaOH to adjust pH>7 AND extracted by DCM, then the residue was concentrated and purified by column chromatography on silica gel using PE-EtOAc as the eluent, to give A-4; yield: 121 mg (73%);

With the complex challenges of chemical substances, we look forward to future research findings about 4488-22-6,belong chiral-catalyst compound

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

It is a common heterocyclic compound, the chiral-catalyst compound, [1,1′-Binaphthalene]-2,2′-diamine, 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

[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 BINAM (100 mg, 0.35 mmol) and pyridine (85 mL, 1.05 mmol) inacetnitrile (3.5 mL) was added p-toluenesulfonylchloride (73 mg, 0.38 mmol), and the mixture was refluxed for 12 h. After cooling to ambient temperature, the reaction was quenched with brine (10 mL) and extracted with EtOAc (15 mL¡Á 3). The combined organic extracts were dried (MgSO4) and concentrated. The residue was purifiedby column chromatography on silica gel using hexane-EtOAc as the eluent, to give A-2; yield: 119 mg (78%).

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; 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

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

Sodium nitrite (1.2g, 18.0mmol) in 3mL of water was added slowly to a stirred solution of BINAM (1.2g, 4.0mmol) and HBF4 (45% in H2O, 10mL) at 0C. Then the reaction was stirred at 0C for 30min and further stirred at room temperature for 30min. The resulting yellow solid was filtered using a Buechner funnel and washed with cold HBF4 (2¡Á5mL), H2O (2¡Á10mL) and EtOH (10mL). The diazonium salt 1 solid (1.8g) was dried under a vacuum desiccator and stored at 0C (yellow solid).

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

Reference£º
Article; Ganapathy, Dhandapani; Sekar, Govindasamy; Catalysis Communications; vol. 39; (2013); p. 50 – 54;,
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 mixture of BINAM (852 mg, 3.0 mmol) and HOAc (1.8 Ml, 30mmol) was added acetic anhydride (312 muL, 3.3 mmol), and the solution was stirred at room temperature overnight. NaOH was added until pH > 7 to quench the reaction, and the solution was extracted with DCM (15 mL¡Á 3). The combined organic extracts were dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel using hexane-EtOAc as the eluent, to give A-1; yield: 880 mg (89%).

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

[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

General procedure: To a two-neckedround-bottomed flask (50 mL) equipped with a three-way stopcock and a magnetic stir bar, was added diamine 1a (56.8 mg, 0.2 mmol) under the air. The vessel was capped with a rubber septum, evacuated,and refilled with N2 gas for three times, and MeCN (20 mL) was added through the septum. The resulting solution was cooled to -40 C. To the solution, was added DIH (151.9 mg, 0.4 mmol) under a stream of N2 gas at -40 C. The resulting solution was stirred for 7 h 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, which was purified by flash column chromatography (eluent: hexane/EtOAc 5:5) on NH silica gel to give product 2a (38.9 mg, 69%). Further purification was carried out by recrystallization from acetone.

As the rapid development of chemical substances, we look forward to future research findings about 4488-22-6

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Article; Okazaki, Masato; Takahashi, Kosuke; Takeda, Youhei; Minakata, Satoshi; Heterocycles; vol. 93; 2; (2016); p. 770 – 782;,
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

General procedure: To an oven-dried Schlenk flask were added diamine 3 (1.0 equiv),Pd2(dba)3 (5 mol%), rac-BINAP (10 mol%), NaOtBu (3.0 equiv), and toluene under Ar atmosphere.Then 8-haloqunoline 4 (2.2 equiv) was added directly. The flask was sealed, and the reaction wasstirred at 85 C until the complete consumption of the starting material 3. The mixture was cooled toroom temperature, filtered through a silica plug, and the plug was washed with EA. The combinedfiltrates were concentrated under reduced pressure, and the residue was purified by silica gelchromatography to give the desired product Ln.

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

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Article; Liu, Wen-Bo; Usman, Muhammad; Wu, Lin-Yang; Molecules; vol. 25; 4; (2020);,
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

General procedure: In a typical experiment, Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), 2-iodobornene 3 (0.5 or 1mmol), 2,2?-diamino-1,1?-binaphthalene (0.25 or 0.5mmol) and triethylamine (0.5ml) were dissolved in DMF (10mL) under argon in a 100mL 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 carried out for the given reaction time with stirring at 50C and analysed by TLC. The mixture was then concentrated and evaporated to dryness. The residue was dissolved in chloroform (20ml) and washed with water (3x20mL), 5% hydrochloric acid (20mL), saturated NaHCO3 (20mL) and brine (20mL). The organic phase was dried over Na2SO4, filtered and evaporated to a solid material. After doing an NMR analysis, all compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200mm), EtOAc/CHCl3 or EtOAc/hexane/CHCl3 eluent (the exact ratios are specified in Characterisation (Section 4.4) for each compound).

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

Reference£º
Article; Mikle, Gabor; Boros, Borbala; Kollar, Laszlo; Tetrahedron Asymmetry; vol. 27; 9-10; (2016); p. 377 – 383;,
Chiral Catalysts
Chiral catalysts – SlideShare

A common heterocyclic compound, the chiral-catalyst compound, name is [1,1′-Binaphthalene]-2,2′-diamine,cas is 4488-22-6, mainly used in chemical industry, its synthesis route is as follows.,4488-22-6

To a solution of 2 (1.421 g, 5 mmol) in benzene (5 mL) was added allylalcohol (0.850 mL, 12.5 mmol) and dried molsieve (1 g, 4 A) and the mixture was degassed. Subsequently, Ti(i-OPr)4, (710 mg, 740 muL, 2.5 mmol), PPh3 (105 mg, 0.4 mmol), and Pd(OAc)2 (22.5 mg, 0.1 mmol) was added and the reaction was stirred under Ar at 50 C. The conversion was monitored by TLC. After extractive work-up with DCM/water, drying (MgSO4), and evaporation, the crude product was purified by chromatography in EtOAc (5?20%)/heptane to afford 1.55 g (85%) of 6 as a slightly brown crystaline solid; m.p.: 95-99 C. 1H-NMR delta = 7.87 (d, J = 9.0 Hz, 2H); 7.78 (dm, J = 7.7 Hz, 2H); 7.21 (d, J = 9.1 Hz, 2H); 7.14-7.22 (m, 4H); 6.99 (dm, J = 7.9 Hz, 2H); 5.77 (ddm, J = 17.3, 10.3 Hz, 2H); 5.12 (dm, J = 17.3 Hz, 2H); 5.02 (dm, J = 10.3 Hz, 2H); 3.92 (br.s, 2H); 3.77-3.86 (br.m, 4H). 13C-NMR delta = 144.2 (C); 135.7 (CH); 133.9 (C); 129.5 (CH); 128.1 (CH); 127.7 (C); 126.7 (CH); 123.9 (CH); 122.0 (CH); 115.6 (CH2); 114.2 (CH); 112.0 (C); 46.1 (CH2). HRMS calcd for C26H25N2 [M + H]+: 365.2018; found: 365.2011.

As the rapid development of chemical substances, we look forward to future research findings about 4488-22-6

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