Tag: M.W:200-300

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO41,mainly used in chemical industry, its synthesis route is as follows.,602-09-5

7H-Dibenzo[c,g]carbazole (12c): 30 g (0.105 mol) of 1,1′-binaphthalene-2,2′-diol (BINOL), 30 g (0.224 mol) of (NH4)2SO3¡¤H2O and 90 ml of 26 % NH4OH was heated at 200C in a 160 ml autoclave (Parr Instrument) for 5 days (after 48 h the pressure dropped from 45 to 18 bar). Upon cooling down, the crude matter was washed with boiling water, dissolved in a 1:1 mixture of EtOH:HCl (conc.), extracted with hot toluene (3×200 ml) and concentrated under vacuum. Residual starting material was removed by extraction with 2M NaOH solution (3×200 ml). Organic layers were combined, dried over Na2SO4, filtered, concentrated and chromatographed on a SiO2 column (50 % DCM in hexanes). Yield: 7.7 g (27 %) of dark-yellow crystalline solid. M.p. 154-156C. 1H NMR (CDCl3, 300 MHz): delta 9.22 (d, J=8.5, 2H), 8.79 (br, s, 1H), 8.05 (dd, J=8.1, 1.3, 2H), 7.89 (d, J=8.7, 2H), 7.74-7.65 (m, 4H), 7.53 (ddd, J=8.0, 6.9, 1.0, 2H).

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

Reference£º
Article; Kerner, Luka?; Gmucova, Katarina; Ko?i?ek, Jozef; Pet?i?ek, Vaclav; Putala, Martin; Tetrahedron; vol. 72; 44; (2016); p. 7081 – 7092;,
Chiral Catalysts
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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 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%).

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; Zhang, Yu; Mao, Mao; Ji, Yi-Gang; Zhu, Jie; Wu, Lei; Tetrahedron Letters; vol. 57; 3; (2016); p. 329 – 332;,
Chiral Catalysts
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.602-09-5,[1,1′-Binaphthalene]-2,2′-diol,as a common compound, the synthetic route is as follows.

stirrer, condenser, and a glass reactor equipped with a thermometer, (RS)-1,1′-bi-2-naphthol 32.0 g (0.112 mol), ethylene carbonate 22. 5g (0.256mol), was charged with potassium carbonate 1.6g and toluene 32g, after a heated slurry state up to 110 , and reacted for 10 hours at 110 .A result that was confirmed by HPLC, the remaining amount of 1,1′-bi-2-naphthol was 0.1% or less.After dilution with toluene 416g to the reaction mixture, the organic solvent phase containing the reaction mixture was washed with 10% aqueous sodium hydroxide 48 g, then the wash water was washed with water until neutral.After washing with water, was refluxed dehydrated organic solvent phase, then cooled to room temperature, filtered, the white crystals dried to (RS)-2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene compound obtained (83.3% yield, HPLC purity 99.7%, YI value: 2.8)., 602-09-5

602-09-5 [1,1′-Binaphthalene]-2,2′-diol 762831, achiral-catalyst compound, is more and more widely used in various fields.

Reference£º
Patent; TAOKA CHEMICAL COMPANY LIMITED; MATSUURA, TAKASHI; KAWAMURA, MIO; HIRABAYASHI, SHUNICHI; FUJII, KATSUHIRO; (9 pag.)JP6083900; (2017); B2;,
Chiral Catalysts
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Name is 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 7181-87-5, its synthesis route is as follows.,7181-87-5

General procedure: General Method: To a 20 mL solution of 1.1 equivalents of nickelocene (41 mg, 0.22 mmol) in anhydrous THF, the respective imidazolium NHC precursor (0.2 mmol) was added as a solid. The resulting suspension was then refluxed for 4 h. The general method was modified for 4, 5 and 6. The reactions involving the formation of more electron-deficient 4 and 5 required 10 h at reflux with 2 equivalents of nickelocene (75 mg, 0.4 mmol). Synthesis of 6 was achieved after 16 h of reflux in the presence of 2.6 equivalents of nickelocene (98 mg, 0.52 mmol). The compounds were then purified by column chromatography. Details available in the Supporting information.

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide

Reference£º
Conference Paper; Luca, Oana R.; Thompson, Bennett A.; Takase, Michael K.; Crabtree, Robert H.; Journal of Organometallic Chemistry; vol. 730; (2013); p. 79 – 83;,
Chiral Catalysts
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As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is [1,1′-Binaphthalene]-2,2′-diol, and cas is 602-09-5, its synthesis route is as follows.,602-09-5

Example 26; 1.0 g NaOH, 20 ml water and 2.8 g 2,2′-dihydroxy-1,1′-binaphthyl prepared in the step a) of the Example 19 are added to a round bottom flask with the volume of 100 mL and are then stirred to be dissolved, 4.1 g n-butyl bromine, 0.2 g tetrabutylammonium bromide and 10 ml ethanol are dropwise added to the round bottom flask, the temperature of the water bath is maintained at 70 C., and after the reaction is performed for 4 hours, the reaction product is poured, while hot, into 50 g crushed ice, followed by stirring to further separate crystal out. The crystal is filtered the filter cake is washed with alkali solution and icy water to obtain light yellow granular solid. The solid is recrystallized with ethanol to obtain yellow-white crystal 2,2′-dibutoxy-1,1′-binaphthyl with the yield of 92.3%, the melting point of 85 C. and the content, according to HLPC detection, of 96.6%.

With the complex challenges of chemical substances, we look forward to future research findings about 602-09-5,belong chiral-catalyst compound

Reference£º
Patent; Wang, Licai; Gao, Zhanxian; Li, Wei; Zheng, Guotong; Dong, Qingxin; Liu, Riping; Wang, Xiaohuan; Zhang, Nan; Wang, Jingzhuang; Cai, Shimian; US2011/301385; (2011); A1;,
Chiral Catalysts
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As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is (1R,2S)-2-Amino-1,2-diphenylethanol, and cas is 23190-16-1, its synthesis route is as follows.,23190-16-1

A solution of HBTU in DMF (1 M, 0.048 ML) was added to a mixture of (R)- 3-benzo [b] THIOPHEN-3-YL-2-PHENYLMETHANESULPHONYLAMINO-PROPIONIC acid (Intermediate 1,15 mg. 0.04 MMOL) and (1 R, 2S)-(-)-2-AMINO-1, 2-DIPHENYLETHANOL (10.2 mg, 0.048 MMOL) in DMF (0.1 ML). The mixture was treated briefly in an ultrasonic bath to ensure complete solution of reagents and the solution was stored at room temperature for 3 days. Purification by preparative hplc (see Methods) gave the desired product, 7.3 mg (32%), HPLC/MS Rt 5.89 min, m/z 571.

With the complex challenges of chemical substances, we look forward to future research findings about 23190-16-1,belong chiral-catalyst compound

Reference£º
Patent; DE NOVO PHARMACEUTICALS LIMITED; WO2004/20402; (2004); A1;,
Chiral Catalysts
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(R)-2′-amino-[1,1′-binaphthalen]-2-ol, cas is 137848-28-3, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,137848-28-3

General procedure: Modified method [69]. Salicylaldehyde (1.22 g, 10.0 mmol) was mixed with (R)-2-amino-2′-hydroxy-1,1′-binaphthyl (2.85 g,10.0 mmol) in dry toluene (50 mL). A few 4 A molecular sieves were added, and the solution was warmed up to 70 C and kept for two days at this temperature. The solution was filtered, and the filtrate was concentrated to 10 mL. Yellow microcrystals 1H2 were isolated when this solution was kept at -20 C for two days. Yield: 3.31 g (85%). M.p.: 120-122 C. 1H NMR (C6D6): d 12.45 (s, 1H, OH), 8.23 (s, 1H, CHN), 7.83 (m, 2H, aryl), 7.74 (m, 2H,aryl), 7.57 (d, J = 8.4 Hz, 1H, aryl), 7.36 (m, 1H, aryl), 7.28 (m, 2H, aryl), 7.17 (m, 2H, aryl), 7.11 (m, 2H, aryl), 6.96-6.83 (m,3H, aryl), 6.62 (t, J = 7.2 Hz, 1H, aryl), 4.73 (s, 1H OH). These spectroscopicdata were in agreement with those reported in the literature [69].

With the rapid development of chemical substances, we look forward to future research findings about (R)-2′-amino-[1,1′-binaphthalen]-2-ol

Reference£º
Article; Chen, Liang; Zhao, Ning; Wang, Qiuwen; Hou, Guohua; Song, Haibin; Zi, Guofu; Inorganica Chimica Acta; vol. 402; (2013); p. 140 – 155;,
Chiral Catalysts
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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.

Racemic 1,1?-binaphthalenyl-2,2?-diamine (2.84 g, 10 mmol) was dissolved in freshly distilled No.7 acetonitrile (60 mL), then No.8 potassium carbonate (13.82 g, 100 mmol) and No.9 potassium iodide (1.33 g, 8.0 mmol) were added. The reaction mixture was heated to reflux under nitrogen atmosphere. Then No.10 ethyl bromoacetate (8.35 g, 50 mmol) was added dropwise and the reaction mixture was refluxed for 72 h. The mixture was then cooled, diluted with water (200 mL) and extracted with ethyl acetate (3 ¡Á 60 mL). The combined organic layer was washed with water (60 mL), dried with MgSO4, and then filtered and evaporated under reduced pressure to remove the solvent. The residue was purified by flash chromatography on silica using No.11 ethyl acetate-petroleum ether (v/v 1:6) as eluent to give light yellow No.12 solid. (yield 54%): 1H NMR (500 MHz, DMSO-d6): 7.86-7.90 (m, 4H), 6.90-7.34 (m, 8H), 3.68-3.85 (m, 16H), 1.02 (t, 12H, J = 7.1 Hz). (0006) A mixture of above resulted solid product (3.15 g, 5 mmol), ethanol (50 mL) and 2 M aqueous solution of NaOH (8 mL) was refluxed under nitrogen atmosphere for 24 h. The solution was then evaporated to remove most solvent, and then cooled in ice-water, 3 M hydrochloric acid was added until pH 3-4. The crude product was extracted with ethyl acetate (2 ¡Á 60 mL). The organic layers were combined and washed with brine (80 mL), dried with Na2SO4, and filtered. The solvent was then removed under reduced pressure. The residue was purified by flash chromatography on silica using ethyl acetate as eluent, from which a yellowish solid of H4L ligand was collected in 76% yield. Mp: 172-173 C; 1H NMR (500 MHz, DMSO-d6) 7.91 (d, 2H, J = 9.0 Hz), 7.86 (d, 2H, J = 8.0 Hz), 7.42 (d, 2H, J = 8.0 Hz), 7.31 (t, 2H, J = 8.0 Hz); 7.19 (t, 2H, J = 8.0 Hz); 6.88 (d, 2H, J = 8.6 Hz); 3.66 (s, 8H); 13C NMR (125.77 MHz, DMSO-d6):172.67, 147.89, 134.27, 130.18, 128.89, 128.38, 126.85, 125.10, 124.47, 124.16, 123.24, 53.13; IR (KBr, cm-1), 3418 (w), 3056 (w), 2929 (m), 1719 (s), 1619 (m), 1594 (m), 1507 (s), 1407 (w), 1375 (w), 1211 (s), 969 (s), 816 (s), 750 (s); Anal. Calc. for C28H24N2O8: C, 65.11; H, 4.68; N, 5.42. Found: C, 65.29; H, 4.53; N, 5.36%., 4488-22-6

Big data shows that 4488-22-6 is playing an increasingly important role.

Reference£º
Article; Huang, Wan-Yun; Chen, Zi-Lu; Zou, Hua-Hong; Liu, Dong-Cheng; Liang, Fu-Pei; Polyhedron; vol. 50; 1; (2013); p. 1 – 9;,
Chiral Catalysts
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.602-09-5,[1,1′-Binaphthalene]-2,2′-diol,as a common compound, the synthetic route is as follows.

602-09-5, 150.0 g (523.88 mmol) of 1 ,1 ‘-bi-2-naphthol (compound II), 138.37 g (1571 .3 mmol) of ethylene carbonate (3 equiv.) and 21 .75 g (157.13 mmol) of potassium carbonate (30 mol-%) in 1 L toluene were heated under reflux for at least 5 to 6 hours, by maintaining argon atmosphere. During the reaction gas evolves. The reaction is monitored by TLC using TBME as solvent. When TLC indicates complete reaction the slightly yellow reaction mixture is cooled to 70C and mixed with 100 g of water (Caution: CO2 gas evolution) The reaction mixture is then stirred for further 10-15 min at 70C to dissolve potassium carbonate. The stirrer is stopped and phases are separated at about 70C. The organic phase is washed with 100 g of 5% w/w aqueous solution of NaOH at 80- 90C for at least 1 h (Caution: CO2 gas evolution), followed by washing with water (each 100 mL) at 70C, until the pH of the washing water is neutral (pH 7). 15 g of charcoal is optionally added to the organic phase and the mixture is stirred at 70C for 30 min. Then the warm solution is filtered through Celite. The clear and slightly yellowish filtrate is cooled to RT and product crystallizes in the form of thin platelets. The solid is filtered off, washed with toluene and dried. 142-170 g (72.4-86.7 %) of the title compound are obtained as a white, dry solid.

The synthetic route of 602-09-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; REUTER CHEMISCHE APPARATEBAU KG; REUTER, Karl; ANDRUSHKO, Vasyl; KANTOR, Mark; STOLZ, Florian; KATO, Noriyuki; KONDO, Mitsuteru; SHIRATAKE, Munenori; ISHIHARA, Kentarou; IKEDA, Shinnya; SUZUKI, Shouko; HIROSE, Kouji; OSHIMA, Kensuke; NAGAYAMA, Shyouya; (45 pag.)WO2019/43060; (2019); A1;,
Chiral Catalysts
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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

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%);, 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; 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