Category: chiral-catalyst

1121-22-8, trans-Cyclohexane-1,2-diamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a solution containing 1,6-diisocyanatohexane (2.35 grams, 13.95 mmol; obtained from Sigma-Aldrich Fine Chemicals) and anhydrous hexane (100 mL, obtained from Sigma-Aldrich Fine Chemicals) stirring at room temperature was added diethylene glycol butyl ether (2.27 grams, 14.0 mmol, obtained from Sigma-Aldrich Fine Chemicals), which was previously dried over calcium chloride granules, and dibutyltin dilaurate as catalyst (0.095 grams, 0.15 mmol, obtained from Sigma-Aldrich Fine Chemicals). The mixture was stirred and heated to an internal temperature of about 45 C. The progress of the reaction was monitored by 1H-NMR spectroscopy for the consumption of the diethylene glycol butyl ether starting material. The mixture was cooled to about 15 C. internal temperature; thereafter, to this mixture was added dropwise a solution of trans-1,2-diaminocyclohexane (0.80 grams, 7.0 mmol; obtained as a racemic mixture of (1R,2R and (1S,2S) stereoisomers from Sigma-Aldrich Fine Chemicals) dissolved in anhydrous hexane (20 mL). The mixture was stirred for about 30 minutes while warming up to room temperature, and FTIR spectroscopic analysis of a reaction sample indicated no unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). The crystalline product was isolated by vacuum filtration on filter paper, rinsed with hexane, and then dried in air to give 4.82 grams of a white powder (88.8% yield). The product was believed to be of the formulae 1H-NMR spectroscopic analysis of the solid was performed in DMSO-d6 (300 MHz) at 80 C. and indicated the above structure with the following assigned peaks: 0.90 ppm (multiplet, 3 H integration, -OCH2CH2OCH2CH2OCH2CH2CH2CH3); 1.05-1.95 ppm (broad multiplets, 16 H integration, 4 methylene protons from butyl ether terminus, 8 methylene protons from the 1,6-diisocyanatohexane portion, and 4 methylene protons from the cyclohexane ring portion); 3.0 ppm (narrow multiplet, 5 H integration, -NH(CO)NHCH2(CH2)4CH2NH(CO)O and also tertiary methine proton adjacent to urea group on cyclohexane ring); 3.40-3.70 ppm (multiplets, 8 H integration, NH(CO)OCH2CH2OCH2CH2OCH2CH2CH2CH3); 4.10 ppm (singlet, 2 H integration, NH(CO)OCH2CH2OCH2CH2OCH2CH2CH2CH3); 5.60 ppm and 5.70 ppm (each a broad singlet, 1 H integration, urea NH protons); 6.75 ppm (broad singlet, 1 H integration, urethane NH proton). Elemental analysis calculated for C: 58.83%, H: 9.54%, N: 10.83%; found for C: 58.81%, H: 9.58%, N: 12.17%.

1121-22-8, 1121-22-8 trans-Cyclohexane-1,2-diamine 43806, achiral-catalyst compound, is more and more widely used in various fields.

Reference£º
Patent; Xerox Corporation; US2006/122415; (2006); A1;,
Chiral Catalysts
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Name is 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 250285-32-6, its synthesis route is as follows.,250285-32-6

General procedure: conditions 1), NHC.HCl (1.0mmol) was dissolved/suspended in 5mL water. Tollens? reagent was prepared by mixing silver(I) oxide (127mg, 0.548mmol) and concentrated ammonia (0.73mL, 15.3mol/L, 11mmol) until complete dissolution. The reagent was diluted with quantum satis water for a final volume of 5mL. An instantaneous precipitation was observed. After 30minat RT, the white solid was filtered and washed with water. Conditions 2), NHC.HCl (1.0mmol) was dissolved/suspended in 10mL of water or ethanol. Silver(I) oxide (127mg, 0.549mmol) and ammonia (0.65mL, 15.3mol/L, 9.9mmol) were added. After 30-200min at RT, the white solid was isolated by filtration and washed with water (IMes, SIMes) or ethanol (IPr, SIPr).

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride

Reference£º
Article; Gibard, Clementine; Fauche, Kevin; Guillot, Regis; Jouffret, Laurent; Traikia, Mounir; Gautier, Arnaud; Cisnetti, Federico; Journal of Organometallic Chemistry; vol. 840; (2017); p. 70 – 74;,
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.173035-10-4,1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride,as a common compound, the synthetic route is as follows.

A mixtureof 2,4,6-trimethylaniline (11.9 g, 0.088 mol), triethyl orthoformate (7.1 g, 0.048 mol)and acetic acid (0.12 mL) was heated at reflux (?120 ) for 5 h. The mixture wasevaporated until dry under reduced pressure. A mixture of dichloroethane (25 mL)and diisopropylethylamine (8.9 mL, 0.05 mol) was added to the precipitate and afterthat the suspension was stirred at 120 for 5 h in a hermetically sealed Schlenkflask. The formed solution was evaporated to dryness under reduced pressure. Theobtained precipitate was washed with acetone (85 mL) and dried under vacuum at rt.The residue was dissolved in chloroform (300 mL) at 0 C, and then granulatedNaOH (68.0 g, 1.70 mol, with a pellet diameter of ?0.5 mm) was added in one portionto the solution at the same temperature under vigorous stirring. Stirring wascontinued until the temperature reaches 18 C (?40 min), then the reaction wasstirred at this temperature for another 4 h (until the end of the heat release process).The precipitate (NaOH) was filtered off, washed with chloroform (2 ¡Á 40 mL) andhexane (2 ¡Á 40 mL). After the last operation, sodium hydroxide can be used onemore time in the same step. The filtrate was evaporated under reduced pressure.The solid residue was treated with hexane (70 mL) under ultrasonic irradiation for 10min and then held at 4 C for 24 h. The precipitate was filtered off, suspended withmethanol (60 mL), treated by ultrasonic irradiation for 2 min and filtered off. The lastoperation was repeated three more times, after that the white powder was driedunder vacuum at rt to give 14.3 g of the title compound 9 (87% relative to the starting2,4,6-trimethylaniline) with >95% purity (by 1H NMR)., 173035-10-4

173035-10-4 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride 2734917, achiral-catalyst compound, is more and more widely used in various fields.

Reference£º
Article; Polyanskii, Kirill B.; Alekseeva, Kseniia A.; Raspertov, Pavel V.; Kumandin, Pavel A.; Nikitina, Eugeniya V.; Gurbanov, Atash V.; Zubkov, Fedor I.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 769 – 779;,
Chiral Catalysts
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Name is trans-Cyclohexane-1,2-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 1121-22-8, its synthesis route is as follows.,1121-22-8

A 10 mL sample solution containing 1.0 mg/L of trans-cyclohexane-1,2-diamine was placed in a centrifuge tube with narrow neck (~4 mm i.d.), which was specially designed for ease of removing the supernatant phase. A mixture of 1 mL disperser solvent and 300 muL extracting solvent with 2 mmol L-1 of chiral selector was rapidly injected into the sample solution using a 5.0 mL syringe, and mixed by vortex mixer at 500 rpm stirring rate for 20 min, so that a cloudy solution was formed. The cloudy solution was centrifuged for 5 min at 3500 rpm, and the extraction product (supernatant phase) was collected in the neck of the tube. Finally, this supernatant phase was derivatized and injected into the HPLC. All of the experiments were carried out in triplicate and the average of the result was reported.

With the complex challenges of chemical substances, we look forward to future research findings about trans-Cyclohexane-1,2-diamine

Reference£º
Article; Hashemi, Majid; Hadjmohammadi, Mohammad Reza; Tetrahedron Asymmetry; vol. 28; 3; (2017); p. 454 – 459;,
Chiral Catalysts
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As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO192,mainly used in chemical industry, its synthesis route is as follows.,14098-24-9

General procedure: The carbonyl substrate (0.1 g) is dissolved in 1-2 mL of anhydrous CHCl3 and 2.0 equiv of a benzocrown ether is added to the solution. To this mixture, CF3SO3H (8.0 equiv; H2SO4 may be used in some cases) is added dropwise with stirring. The reaction is stirred at room temperature for at least 2 h, after which, the mixture is poured over several grams of ice. The resulting solution is extracted three times with CHCl3. The organic phase is subsequently washed three times with water and dried over MgSO4 solution. Removal of the solvent provides the product.

With the complex challenges of chemical substances, we look forward to future research findings about Benzo-18-crown 6-Ether,belong chiral-catalyst compound

Reference£º
Article; Zielinski, Matthew E.; Tracy, Adam F.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1701 – 1704;,
Chiral Catalysts
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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, Example 43 Synthesis of N2-cyclohexylmethyl-N4-((S)-1-ethyl-pyrrolidin-2-ylmethyl)-N6-(3-fluoro-4-methoxphenyl)-1,3,5-triazine-2,4,6-triamine (141) To a mixture of cyanuric chloride (0.368 g, 2 mmol) in CH3CN at about -20¡ã C. was added 3-fluoro-p-anisidine (0.28 g, 2 mmol) in CH3CN followed by the addition of N,N-diisopropylethylamine (DIEA) (0.35 mL, 2 mmol) and stirred for about 1 hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then, cyclohexylmethyl amine (0.26 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at RT. Then, S-(-)-2-aminomethyl-N-ethyl pyrrolidine (0.29 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated under reduced. The crude material was purified by column chromatography eluding with 96:3:1 methylene chloride:methanol:conc. ammonium hydroxide to yield a white solid 141 (0.400 g, 43.7percent), mp 68-69¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 8.2 min, 97.1percent purity; MS (ESI): m/z 458 (M+H, 100), 362 (2.8), 230 (85.4).

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

Reference£º
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
Chiral Catalysts
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As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO297,mainly used in chemical industry, its synthesis route is as follows.,33100-27-5

General procedure: A solution of (2 mmol, 0.4 ml) of 15-crown-5 in (10 ml) of absolute ethanol was added to a solution of (1 mmol, 0.933 gm Pr-picrate), (0.936 gm Nd-picrate) and (0.900 gm Dy-picrate) in (10 ml) of absolute ethanol and refluxed at (50 ? 60 oC) for (1 hr.). The solution was concentrated at (40 ? 50 oC) to a very small volume (till the formation of a precipitate), usually a gummy precipitate forms which was treated with (40 ? 60 oC) petroleum ether until all the gummy precipitate was converted to a fine yellow ? orange powder. The precipitate was collected and stored in a desicator for complete dryness. These complexes were also prepared by another method, by stirring a solution of 15-crown-5 with a solution of lanthanide picrate for (24 ? 48 hrs.). The gummy precipitates were treated with petroleum ether. The yields were (92 ? 96percent)24.

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
Article; Al-Amery, Mohammed H. A.; Al-Abdaly, B. Ibrahim; Albayaty, M. Kahtan; Oriental Journal of Chemistry; vol. 32; 2; (2016); p. 1025 – 1048;,
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.1121-22-8,trans-Cyclohexane-1,2-diamine,as a common compound, the synthetic route is as follows.

12.65 g of anhydrous magnesium sulphate (105.1 mmoles) and 4.2 ml of a racemic trans-1,2-diaminocyclohexane mixture (35.0 mmoles) were successively added to a solution of 6.66 ml of 2-pyridylaldehyde (70.0 mmoles) in 50 ml of absolute ethanol. The reaction mixture was stirred for 20 hours at ambient temperature (the solution turned yellow after stirring for three hours), heated for 2.5 hours under reflux, then filtered through a frit. The isolated solid was washed with dichloromethane. The total filtrate was concentrated completely under reduced pressure to isolate an ochre solid, which was re-crystallised from ethanol. 8.2 g of pale yellow crystals were obtained, which corresponded to a 80.1% yield. The characteristics were as follows: M.Pt: 140-141 C. (EtOH) (racemic mixture) (Lit: 127-129 C.: obtained by Belokon, Y N; North, M: Churkina, T D; Ikonnikov, N S; Maleev, V I; Tetrahedron 2001, 57, 2491-2498 for the stereoisomer 1S,2S, hexane-MeOH); 1H NMR/CDCl3: delta 8.51 (m, 2H, H1,2), 8.28 (s, 2H, H7,14), 7.84 (m, 2H, H4,17), 6.55-7.64 (m, 2H, H5,16), 7.14-7.21 (m, 2H, H3,18), 3.50 (m, 2H, H8,13), 1,81 (m, 6H, H10,11 and H carried by carbons 9 and 12 located in the position cis (or trans) with respect to the adjacent nitrogen atoms), 1.40-1.53 (m, 2H, H carried by carbons 9 and 12 located in the trans (or cis) position with respect to the adjacent nitrogen atoms). 13C NMR/CDCl3: delta 161.42 (C7 and C14), 154.61 (C6 to C15), 149.21 (C1 and C2), 136.39 (C4 and C17), 124.43 (C3 and C18), 121.29 (C5 and C16), 73.53 (C8 and C13), 32.70 (C9 and C12), 24.33 (C10 and C11). FAB+ (NBA matrix): 293 (100%, M+1), 107 (52%, 2-pyridylaldimine+H+), 92 (38%, C5H4N-CH2+), 119 (25%, C5H4N-CHN-CH2+), 294 (23%, M+2), 204 (22%, [M-(2-pyridylidene)]+), 79 (21%, pyridine+), 187 (20%, M-[2-pyridylineamino]+), 585 (1%, 2M+1).

1121-22-8, 1121-22-8 trans-Cyclohexane-1,2-diamine 43806, achiral-catalyst compound, is more and more widely used in various fields.

Reference£º
Patent; Taillefer, Marc; Cristau, Henri-Jean; Cellier, Pascal-Philippe; US2005/234239; (2005); A1;,
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.673-06-3,D-Phenylalanine,as a common compound, the synthetic route is as follows.

673-06-3, In 50ml dried single necked flask, 0.5g(R) -2-amino-3-phenylpropanoic acid dissolved in 4ml THF and 1ml of water, At RT., add 0.127g (1.05eq) of sodium hydroxide to make alkaline, stirred for 30min,cooled to about 0 deg.C. Slowly dropped 0.727g (1.1eq) (Boc)2O in THF solution. Naturally warm to RT and react for 3h. The reaction was stopped, the low temperature regulator 3 to PH = 4 and extracted 5 times with EA and extracted,washed with water and saturated brine, dried and concentrated to give a light brown oil 412mg.

673-06-3 D-Phenylalanine 71567, achiral-catalyst compound, is more and more widely used in various fields.

Reference£º
Patent; Shandong Kaisen Pharmaceutical Co., Ltd.; Wu, Junjun; Li, Rui; Jiang, Xiangsheng; Song, Jiaqi; Yang, Shuangbing; Zhang, Jingyu; Zhang, Erli; (37 pag.)CN105294669; (2016); A;,
Chiral Catalysts
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[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

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