Chiral oxygen ligands

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO455,mainly used in chemical industry, its synthesis route is as follows.,24621-61-2

Example 1 Preparation of (3S)-1-p-Toluenesulfonyloxy-3-triethylsilyloxy-butane (2)To a stirred solution of the (S)-(+)-1,3-butanediol 1 (1 g, 11.1 mmol), DMAP (30 mg, 0.25 mmol) and Et3N (4.6 mL, 3.33 g, 33 mmol) in anhydrous methylene chloride (20 mL) p-toluenesulfonyl chloride (2.54 g, 13.3 mmol) was added at 0 C. The reaction mixture was stirred at 4 C. for 22 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (8:2, then 1:1) to afford the tosylate (2.31 g, 85% yield) as a colorless oil.To a stirred solution of the tosylate (2.31 g, 9.5 mmol) and 2,6-lutidine (1.2 mL, 1.12 g, 10.5 mmol) in anhydrous methylene chloride (15 mL) triethylsilyl trifluoromethanesulfonate (2.1 mL, 2.51 g, 9.5 mmol) was added at -50 C. The reaction mixture was allowed to warm to room temperature (4 h) and stirring was continued for additional 20 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (97:3) to afford the product 2 (2.71 g, 80% yield) as a colorless oil:[alpha]D+18.0 (c 2.38, CHCl3); 1H NMR (400 MHz, CDCl3) delta 7.77 (2H, d, J=8.2 Hz, o-HTs), 7.33 (2H, d, J=8.2 Hz, m-HTs), 4.10 (2H, t, J=6.1 Hz, 1-H2), 3.90 (1H, m, 3-H), 2.43 (3H, s, MeTs), 1.72 (2H, m, 2-H2), 1.10 (3H, d, J=6.2 Hz, 4-H3), 0.88 (9H, t, J=8.0 Hz, 3¡ÁSiCH2CH3), 0.50 (6H, q, J=8.0 Hz, 3¡ÁSiCH2CH3); 13C NMR (100 MHz) delta 144.62 (s, p-CTs), 133.03 (s, i-CTs), 129.72 (d, m-CTs), 127.82 (d, o-CTs), 67.78 (t, C-1), 64.46 (d, C-3), 38.47 (t, C-2), 23.82 (q, C-4), 21.52 (q, MeTs), 6.71 (q, SiCH2CH3), 4.77 (t, SiCH2CH3); MS (EI) m/z 359 (5, MH+), 329 (87, M+-C2H5), 259 (100), 233 (54), 197 (50), 179 (74), 163 (40), 149 (48), 135 (38), 115 (53), 91 (71); exact mass calculated for C15H25O4SSi (M+-C2H5) 329.1243, found 329.1239.

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-Butane-1,3-diol,belong chiral-oxygen-ligands compound

Reference£º
Patent; DeLuca, Hector F.; Clagett-Dame, Margaret; Plum, Lori A.; Chiellini, Grazia; Grzywacz, Pawel; US2009/170821; (2009); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO296,mainly used in chemical industry, its synthesis route is as follows.,24621-61-2

Example 4 : (R)-2-(3-{3-[[2-Chloro-3-(trifluoromethyl) benzyl] (2,2- diphenylethyl) amino]-1-methyl-propoxy}-phenyl) acetic acid methyl ester ; a) Toluene-4-sulfonic acid- (S)-3-hydroxy-butyl ester; To a stirring solution of (S)-1, 3-butanediol (1.0 g, 0.01 mmol) and triethylamine (1.39 g, 0.014 mmol) in dichloromethane (10 mL) at-20C was added dropwise p-toluenesulfonyl chloride and the mixture was stirred for 2 h. The reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was poured into cold H2O (20 mL), and extracted three times with dichloromethane. The organic extracts were then washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give 2.6 g (96% yield) of title compound as an oil. MS (ESI) 244.8 (M+). The crude tosylat was used without further purification.

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-Butane-1,3-diol,belong chiral-oxygen-ligands compound

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2003/82802; (2003); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

1,5-Diphenylpenta-1,4-dien-3-one, cas is 538-58-9, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.

.) Synthesis According to Inorganic Synthesis, 28, 110 (1990)The synthesis is carried out under inert gas. 2.096 g (11.73 mmol) PdCl2 and 0.686 g (11.73 mmol) NaCl are provided under argon, and 59 ml of methanol are added.Next the reaction mixtures is stirred over night for 18 hours in the sealed flask. Then the dark red-brown solution is filtered through a G3 frit under argon. No residue is evident on the frit.The filtrate solution is transferred to a 500 ml three-necked flask using 293 ml of methanol, and heated to 60 C. At this temperature, 8.563 g (36.54 mmol) dibenzylidene acetone are added under argon. Then, the addition of 17.595 g (214.49 mmol) sodium acetate is made.A voluminous, reddish solid precipitates. Subsequently, the reaction mixture is cooled to room temperature. The product is removed by filtration and washed with 300 ml of methanol, 300 ml of water, and 300 ml of acetone. The product is dried in vacuo at room temperature.Appearance: dark-brown solidSolubility Test:1.00 g of the product are dissolved in 150 ml of chloroform and stirred at room temperature for 30 minutes. The solution is then aspirated through a membrane filter. The filter is washed with 30 ml of water and 30 ml of acetone and subsequently dried over night at 45 C. in vacuo. The residue accounts for 1.4%.Result:m(product): 6.4 gYield with respect to Pd: 94CHCl3-insoluble ingredients: 1.4

With the rapid development of chemical substances, we look forward to future research findings about 1,5-Diphenylpenta-1,4-dien-3-one

Reference£º
Patent; W.C. Heraeus GmbH; US7999126; (2011); B2;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

1,5-Diphenylpenta-1,4-dien-3-one, cas is 538-58-9, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.

General procedure: General procedure (GP): Dienones 2a-m (0.25 mmol) and diamide 1a or 1b (74 mg, 0.25 mmol)were dissolved in 10 mL of dry CH2Cl2 in a 25 mL round bottom flask. DBU (3 eq, 114 mg, 0.75 mmol)was added to the reaction, which was subsequently stirred for 2-3 h. After the reaction was completedas determined by TLC, the crude material was subjected to column chromatography using ethylacetate/n-hexane (2:3) to give the desired compounds 3a-m.

With the rapid development of chemical substances, we look forward to future research findings about 1,5-Diphenylpenta-1,4-dien-3-one

Reference£º
Article; Al-Majid, Abdullah Mohammed; Islam, Mohammad Shahidul; Atef, Saleh; El-Senduny, Fardous F.; Badria, Farid A.; Elshaier, Yaseen A. M. M.; Ali; Barakat, Assem; Motiur Rahman; Molecules; vol. 24; 7; (2019);,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

(S)-Butane-1,3-diol, cas is 24621-61-2, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.

Step E (2-TOLUENE-4-SULFONIC acid 3-hydroxy-butyl ester; A solution of (S)- (+)-1, 3-butanediol (9.5 g, 0.105 mol) and Et3N (12.8 g, 0.126 mol) in CH2C12 (200 mL) is treated with dibutyltin oxide (0.52 g, 2.08 mmol) and THENP-TOLUENESULFONYL chloride (20.09 g, 0.105 mol) is added as a solid in portions over 30 minutes at rt. The resultant mixture is stirred at rt for 17 hours under N2. The reaction is quenched with 1 N HC1 (50 mL), diluted with water and extracted with EtOAc. The organic layer is dried (NA2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 98/2 CH2C12/ACN (to elute the unreactedp-toluenesulfonyl chloride) and then 2/1 hexanes/acetone to afford 18. 67 g (73%) the title compound. Rf== 0.23, Rf bis-tosylate = 0.53 (98/2 CH2C12/ACN).

With the rapid development of chemical substances, we look forward to future research findings about (S)-Butane-1,3-diol

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/19151; (2005); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

1,5-Diphenylpenta-1,4-dien-3-one, cas is 538-58-9, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.

General procedure: In a general procedure, dibenzylidene acetone (1 mmol), N,N-dimethylbarbituric acid/barbituric acid/thiobarbituric acid(1 mmol) and 4 mL of ethanol:water (1:1) were taken in a 50 mL round-bottomed flask. 10 mol% of tetrabutyl ammonium bromide (TBAB) was added to the mixture, and the contents were stirred. The reaction mixture was refluxed and the progress of the reaction was monitored by TLC using ethyl acetate:petroleum ether (30:70) as eluent for disappearance of active methylene compounds. After completion of the reaction, the reaction mixture was allowed to cool to room temperature and diluted with water (5 mL). The solid obtained was filtered at pump and washed with water:ethanol (2:1). The product was recrystallized with ethanol. The products were characterized by their spectral data.

With the rapid development of chemical substances, we look forward to future research findings about 1,5-Diphenylpenta-1,4-dien-3-one

Reference£º
Article; Aggarwal, Komal; Khurana, Jitender M.; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 143; (2015); p. 288 – 297;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

1,5-Diphenylpenta-1,4-dien-3-one, cas is 538-58-9, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.

General procedure: A mixture of malononitrile (2a) (66 mg, 1 mmol), dibenzylideneacetone (6a) (234 mg, 1 mmol), tributylphosphine (25 mL, 0.1 mmol), and anhydrous CH2Cl2 (5.0 mL) was magnetically stirred in a flask under nitrogen atmosphere at room temperature. The reaction progress was monitored by thin layer chromatography (TLC) until the starting materials were completely consumed. Then, the reaction mixture was diluted with H2O (10 mL) and extracted with Et2O (3×10 mL), the organic phase was washed with brine (10 mL), dried over anhydrous Na2SO4. After the removal of the solvent under reduced pressure, the residue was subjected to chromatography on a silica gel (200-300 mesh) column using petroleum ether/ethyl acetate (4:1) as eluent to afford 7a (286 mg, 95% yield) as a light yellow solid (mp 170-171 C).

With the rapid development of chemical substances, we look forward to future research findings about 1,5-Diphenylpenta-1,4-dien-3-one

Reference£º
Article; Xu, Da-Zhen; Zhan, Ming-Zhe; Huang, You; Tetrahedron; vol. 70; 2; (2014); p. 176 – 180;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

1,5-Diphenylpenta-1,4-dien-3-one, cas is 538-58-9, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.

General procedure: A mixture of malononitrile (2a) (66 mg, 1 mmol), dibenzylideneacetone (6a) (234 mg, 1 mmol), tributylphosphine (25 mL, 0.1 mmol), and anhydrous CH2Cl2 (5.0 mL) was magnetically stirred in a flask under nitrogen atmosphere at room temperature. The reaction progress was monitored by thin layer chromatography (TLC) until the starting materials were completely consumed. Then, the reaction mixture was diluted with H2O (10 mL) and extracted with Et2O (3×10 mL), the organic phase was washed with brine (10 mL), dried over anhydrous Na2SO4. After the removal of the solvent under reduced pressure, the residue was subjected to chromatography on a silica gel (200-300 mesh) column using petroleum ether/ethyl acetate (4:1) as eluent to afford 7a (286 mg, 95% yield) as a light yellow solid (mp 170-171 C).

As the rapid development of chemical substances, we look forward to future research findings about 538-58-9

Reference£º
Article; Xu, Da-Zhen; Zhan, Ming-Zhe; Huang, You; Tetrahedron; vol. 70; 2; (2014); p. 176 – 180;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

(S)-Butane-1,3-diol, cas is 24621-61-2, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.

To a solution of (S)+}1,3-butanediol (10.0 g, 0.110 mol), was added triphenylmethylchloride (33.0 g, 0.330 mol), 4-dimethylaminopyridine (1.40 g, 11.5 mmol) in CH2Cl/pyridine (1:1, 500 mL).Stirring was continued over 48 h. The solvent was removed, the mixture was diluted with ether, washed with brine and dried over Na2SO4. The organic solution was filtered and concentrated. Silica gel chromatography with (5% ethyl acetate/hexanes) produced a clear oil (24 g) in 70% yield.

As the rapid development of chemical substances, we look forward to future research findings about 24621-61-2

Reference£º
Patent; Bristol-Myers Squibb Company; Merck & Co. Inc.; US6967196; (2005); B1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

(S)-Butane-1,3-diol, cas is 24621-61-2, it is a common heterocyclic compound, the chiral-oxygen-ligands compound, its synthesis route is as follows.

To a stirring solution of (S)-1, 3-butanediol (1.0 g, 0.01 MMOL) and triethylamine (1.39 g, 0.014 MMOL) in dichloromethane (10 mL) at-20C was added dropwise p- toluenesulfonyl chloride and the mixture was stirred for 2 h. The reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was poured into cold H20 (20 mL), and extracted three times with DICHLOROMETHANE. The organic extracts were then washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give 2.6 g (96% yield) of title compound as an oil. MS (ESI) 244.8 (M+). The crude tosylat was used without further purification.

As the rapid development of chemical substances, we look forward to future research findings about 24621-61-2

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/43939; (2004); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate