Day: October 22, 2020

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

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is 1,3-Dimesityl-1H-imidazol-3-ium chloride, and cas is 141556-45-8, its synthesis route is as follows.,141556-45-8

General procedure: A mixture of pyrazine ligand 1 or 2 (1mmol), Li2PdCl4 (1mmol) and NaOAc (1mmol) in 20mL of dry methanol was stirred for 24hat rt. The yellow solids (yield: 92%) were collected by filtration and washed several times with methanol, which can be assigned to be palladacyclic dimers. Then, a Schlenk tube was charged with the above chloride-bridged palladacyclic dimers (0.5mmol), the corresponding imidazolium salt (1.25mmol) and tBuOK (2.5mmol) under nitrogen. Dry THF was added by a cannula and stirred at room temperature for 3h. The product was separated by passing through a short silica gel column with CH2Cl2 as eluent, the third band was collected and afforded the corresponding carbene adducts 3-10 as yellow solids. The characterization data for 3: Yield: 78%.

With the complex challenges of chemical substances, we look forward to future research findings about 141556-45-8,belong chiral-catalyst compound

Reference£º
Short Survey; Xu, Chen; Wang, Zhi-Qiang; Yuan, Xiao-Er; Han, Xin; Xiao, Zhi-Qiang; Fu, Wei-Jun; Ji, Bao-Ming; Hao, Xin-Qi; Song, Mao-Ping; Journal of Organometallic Chemistry; vol. 777; (2015); p. 1 – 5;,
Chiral Catalysts
Chiral catalysts – SlideShare

22795-99-9, (S)-(1-Ethylpyrrolidin-2-yl)methanamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

22795-99-9, First, 4-benzyloxy-3,5-dimethoxybenzoic acid chloride represented by Formula 85 and [(2S)-1-ethylpyrrolidin-2-yl]methanamine represented by Formula 103 were prepared in 0.2 M solution, respectively, using a toluene solvent. An amine solution (1.2 mL, 0.240 mmol) entered 10 mL vial and a sodium carbonate solution (0.4 mL, 0.200 mmol) was added thereto. Thereafter, a benzoic acid chloride solution (1.0 mL, 0.200 mmol) entered the vial, vigorously shaken and agitated at room temperature for 18 hours. After terminating the reaction, an organic layer was moved to a cartridge tube (6 mL, benzenesulfonic acid, 904030-WJ, UCT) using ethyl acetate. Impurities were removed using methanol (15 mL) while separation and purification were conducted using an elute solution (ethyl acetate/methanol/triethylamine, 20:2:1, v/v/v), resulting in a benzamide compound represented by Formula 13 as a desired product (VVZ-014; 66 mg, 83percent yield). Analysis data of the produced benzamide compound is provided as follows. 1H-NMR (MeOD-d4) d 1.22 (t, 3H), 1.73 (m, 1H), 1.80 (m, 2H), 1.98 (m, 1H), 2.30 (m, 1H), 2.41 (m, 1H), 2.76 (m, 1H), 3.02 (m, 1H), 3.28 (m, 2H), 3.65 (dd, 1H), 3.88 (s, 6H), 5.02 (s, 2H), 7.17-7.46 (m, 7H)

The synthetic route of 22795-99-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Lee, Doo Hyun; US2014/336378; (2014); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

It is a common heterocyclic compound, the chiral-catalyst compound, 6,6′-((1E,1’E)-((2,3-Dimethylbutane-2,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2,4-di-tert-butylphenol), cas is 351498-10-7 its synthesis route is as follows.,351498-10-7

Preparation of Cobalt(ll) Complex used in Step 2: A 50 mL flask was charged with lambda/,lambda/-bis(3,5-di-tert-butylsalicylidene)-1 , 1 ,2,2- tetramethylethenediamine (0.4302 g, 0.78 mmol, 1.0 equiv), EtOH (17 mL), and Co(OAc)2 (0.1385 g, 0.78 mmol, 1.0 equiv). The mixture was degassed and then heated to reflux under nitrogen for 3 h, cooled to room temperature. The precipitate was filtered and the purple solid was washed with EtOH (10 mL) and dried under high vacuum to give 0.3533 g (75%) of the cobalt(ll) complex.

With the complex challenges of chemical substances, we look forward to future research findings about 6,6′-((1E,1’E)-((2,3-Dimethylbutane-2,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2,4-di-tert-butylphenol)

Reference£º
Patent; VITAE PHARMACEUTICALS, INC.; WO2009/88997; (2009); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.673-06-3,D-Phenylalanine,as a common compound, the synthetic route is as follows.

General procedure: A 60 ml of aqueous solution of sodium nitrite (20.7 g, 0.3 mol) was added into a stirred and ice-cooled solution of D-amino acids (9A-C, G, 50 mmol) in 1 M H2SO4 (100 ml, 0.1 mol) over 3 h, and the mixture was stirred for 24 h at room temperature until the completion of the reaction (monitored by ninhydrin). The mixture was adjusted to pH 6 with solid NaHCO3 and then to pH 3 with concentrated HCl followed by freeze-drying. The resulting residue was extracted with hot acetone (4¡Á100 ml), and the extracts were concentrated and dried to offer colorless oil, to which ether (200 ml) was added and filtrated to remove insoluble solids, the filtrate was concentrated and re-crystallized in ether/hexanes mixture to afford 10(A-C, G) as white crystalline, yield 82%-92%., 673-06-3

As the paragraph descriping shows that 673-06-3 is playing an increasingly important role.

Reference£º
Article; Jia, Chao; Yang, Ke-Wu; Liu, Cheng-Cheng; Feng, Lei; Xiao, Jian-Min; Zhou, Li-Sheng; Zhang, Yi-Lin; Bioorganic and Medicinal Chemistry Letters; vol. 22; 1; (2012); p. 482 – 484;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO18,mainly used in chemical industry, its synthesis route is as follows.,33100-27-5

EXAMPLE 1 A mixture of 4-hydroxy-4-[3-(naphth-2-ylmethoxy)phenyl]-tetrahydropyran (1.9 g), sodium hydride (0.27 g of a 50percent w/w dispersion in mineral oil), 1,4,7,10,13-pentaoxacyclopentadecane (hereinafter 15-crown-5, 0.2 g) and tetrahydrofuran (10 ml) was stirred at ambient temperature for 15 minutes. Methyl iodide (0.35 ml) was added and the mixture was stirred at ambient temperature for 15 hours. The mixture was evaporated and the residue was partitioned between diethyl ether and water. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 9:1 v/v mixture of methylene chloride and diethyl ether as eluent. There was thus obtained 4-methoxy-4-[3-(naphth-2-ylmethoxy)phenyl]tetrahydropyran (1.8 g, 94percent), m.p. 66.5¡ã-67.5¡ã C. The 4-hydroxy-4-[3-(naphth-2-ylmethoxy)phenyl]tetrahydropyran starting material was obtained as follows:

With the synthetic route has been constantly updated, we look forward to future research findings about 1,4,7,10,13-Pentaoxacyclopentadecane,belong chiral-catalyst compound

Reference£º
Patent; Imperial Chemical Industries PLC; ICI Pharma; US5098930; (1992); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide, cas is 7181-87-5, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,7181-87-5

(1) Weigh 0.2 mmol (54.8 mg) of 1,3-dimethylbenzimidazole oxime iodide, 0.1 mmol (40.6 mg) of 1,4-diiodobiphenyl (both feed ratios of 2:1) as a substrate, 2 mg of Group IB copper salt Cu(OAc)2¡¤H2O (10 mol% equivalent relative to 1,4-diiodobiphenyl) as a catalyst, 0.2 mmol (16.4 mg) of sodium acetate as an additive, put the substrate, catalyst, additive and mixing into the reaction kettle, An aprotic solvent N,N-dimethylformamide (1 ml) was added as a reaction solvent, and the mixture was reacted at 100 C for 10 hours. After completion of the reaction, dichloromethane (5 ml) was added, filtered, and then washed twice with water (5 ml) and ethanol (5 ml). The obtained yellow filter residue is a pure product biphenyl bridged bisbenzimidazole, the yield was 90%. The nuclear magnetic resonance spectrum is shown in Figure 2: (deuterated dimethyl sulfoxide as solvent, Bruker AMX-400 nuclear magnetic resonance instrument). 1H NMR (400 MHz, DMSO-d6): delta = 8.28 (d, J = 8.0 Hz, 4H), 8.18 (d, J = 4.8 Hz, 4H), 8.11(d, J = 7.6 Hz, 4H), 7.80 (d, J = 4.8 Hz, 4H), 3.98 (s, 12H).High resolution mass spectrometry (Waters-Q-TOF Premier detector). HRMS (ESI) : C30H28IN4+ ([M-I-]+) calc.: 571.1353, Found: 571.1398.

7181-87-5 is used more and more widely, we look forward to future research findings about 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide

Reference£º
Patent; Guilin University of Technology; Li Shiqing; Li Yongshu; Liang Xiajing; Liu Yunfeng; Chen Ziyuan; Pan Meiling; (6 pag.)CN109734670; (2019); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO52,mainly used in chemical industry, its synthesis route is as follows.,673-06-3

The reaction of bromobenzene (0.158 g, 1.0mmol), D-phenylalanine (0.247 g, 1.5 mmol), copper powder (0.0064 g, 0.1 mmol),MI (0.036 g, 0.2 mmol), Cs2CO3 (0.977 g, 3.0 mmol), TBAHS (0.068 g, 0.2 mmol)produced 0.200 g (83%) of phenyl-D-phenylalanine as a white solid.

With the synthetic route has been constantly updated, we look forward to future research findings about D-Phenylalanine,belong chiral-catalyst compound

Reference£º
Article; Zhou, Qifan; Du, Fangyu; Chen, Yuanguang; Fu, Yang; Chen, Guoliang; Tetrahedron Letters; vol. 60; 29; (2019); p. 1938 – 1941;,
Chiral Catalysts
Chiral catalysts – SlideShare

D-Phenylalanine, cas is 673-06-3, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,673-06-3

The 10mmolD-phenylalanie dissolved in 50 ml tetrahydrofuran, ice water bath to 0 C left and right, add triethylamine 20mmol. Then the 15mmol (Boc)2O into to the above-mentioned solution. 0 C left and right, reaction 60 min, then room temperature reaction 15h, after the reaction. The reaction solution with ethyl acetate extraction 2-3 time, remove the upper layer, pH is adjusted with acid, then dichloromethane is used for extraction 2-3 time. Merging the lower organic phase, dried with anhydrous sodium sulfate, concentrated solvent, get intermediate 1

With the synthetic route has been constantly updated, we look forward to future research findings about D-Phenylalanine,belong chiral-catalyst compound

Reference£º
Patent; Zunyi Medical College; Yang, Jiaqiang; Yang, Juan; Ceng, Fakui; Li, Peng; (9 pag.)CN105503947; (2016); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is 1,4,7,10,13-Pentaoxacyclopentadecane, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 33100-27-5, its synthesis route is as follows.,33100-27-5

General procedure: Crystals of compounds 1?3 were prepared by isothermal evaporation fromaqueous solutions at room temperature. The crystals of compound 1 weresynthesized by the reaction of 0.051 g (0.1 mmol) of UO2(NO3)2¡¤6H2O,0.040 g (0.22 mmol) of 12-crown-4, 0.280 g (2.0 mmol) of 40percent H2SeO4,and 2.001 g (111.2 mmol) of deionized distilled water. Compound 2:0.050 g (0.1 mmol) of uranyl nitrate, 0.046 g (0.21 mmol) of 15-crown-5,0.282 g (2.0 mmol) of selenic acid, and 2.012 g (111.7 mmol) of deionizeddistilled water. Compound 3: 0.050 g (0.1 mmol) of uranyl nitrate, 0.046 g(0.21 mmol) of 15-crown-5, 0.282 g (2.0 mmol) of selenic acid, and 2.012 g(111.7 mmol) of deionized distilled water (note: the bulk of crystals herebelongs to compound 2). Homogeneous liquid solutions were left in awatch glass. Yellowish-green flattened crystals formed within 2 weeks.

With the complex challenges of chemical substances, we look forward to future research findings about 1,4,7,10,13-Pentaoxacyclopentadecane

Reference£º
Article; Gurzhiy, Vladislav V.; Tyumentseva, Olga S.; Tyshchenko, Darya V.; Krivovichev, Sergey V.; Tananaev, Ivan G.; Mendeleev Communications; vol. 26; 4; (2016); p. 309 – 311;,
Chiral Catalysts
Chiral catalysts – SlideShare