Chiral oxygen ligands

A common heterocyclic compound, 538-58-9,1,5-Diphenylpenta-1,4-dien-3-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 538-58-9

Bis(dibenzylideneacetone)palladium(0) (Pd(dba)2)was synthesized by reducing PdCl2 with methanol in thepresence of sodium acetate and dba [30]. Dibenzylideneacetone(3.4500 g, 1.472 ¡Á 10-2 mol), sodium acetatetrihydrate (4.8525 g, 3.568 ¡Á 10-2 mol), and methanol(113 mL) were placed in a two-neck round-bottomflask. The reaction mixture was stirred at 50C for 45-60 min to obtain a solution, and PdCl2 (0.7875 g,4.434 ¡Á 10-3 mol) was added. The resulting solutionwas stirred in an argon atmosphere at 40C for 4 h.This yielded a dark violet precipitate of the Pd(dba)2complex, which was collected on a fritted glass filterunder argon, washed with water and acetone, andvacuum-dried (30C/2-3 Torr) for 3 h. The productyield was 2.4 g. (94% of the theoretical yield); m =152C. According to the literature, m of thePd(dba)2 complex is 152C [31]. UV spectra:Pd(dba)2, 525 nm (d ? d* transition, epsilon525 =6400 L mol-1 cm-1); non-coordinated dba, 325 nm(n ? pi* transition, epsilon325 = 33540 L mol-1 cm-1).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1,5-Diphenylpenta-1,4-dien-3-one,538-58-9,its application will become more common.

Reference£º
Article; Skripov; Belykh; Sterenchuk; Akimov; Tauson; Schmidt; Kinetics and Catalysis; vol. 58; 1; (2017); p. 34 – 45; Kinet. Katal.; vol. 58; 1; (2017); p. 36 – 48,13;,
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

24621-61-2 A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

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).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 24621-61-2 reaction routes.

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

538-58-9 A common heterocyclic compound, 538-58-9,1,5-Diphenylpenta-1,4-dien-3-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: To a solution of dialkyl phosphite (0.01 mol) in anhydrous tetrahydrofuran (30 mL),maintained under a nitrogen atmosphere, sodium (0.02 g) was added and the mixture was stirred at roomtemperature until complete dissolution of sodium. Diarylideneketone 1 (0.01 mol) was then added and themixture heated under reflux for 4 h. After cooling, the reaction mixture was diluted with water (50 mL)and extracted with CHCl3 (2 ¡Á 25 mL). The organic phase was dried over Na2SO4 and concentrated undervacuum. The obtained residue was chromatographed on a silica gel column using a mixture of Et2O andhexane 9:1 as an eluent.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 538-58-9 reaction routes.

Reference£º
Article; Lamouchi, Imen; Touil, Soufiane; Heterocycles; vol. 94; 5; (2017); p. 894 – 911;,
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 we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 24621-61-2,(S)-Butane-1,3-diol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.24621-61-2

p-Toluenesulfonyl chloride (381 mg, 1 .68 mmol) was dissolved in anhydrous DCM (10 mL) at RT under N2. (s)-(+)-1 ,3-butandiol (300 muIota_, 3.33 mmol) was added followed by NEt3 (450 muIota_, 3.33 mmol) and the solution stirred for 18 h. The solution was partitioned with H2O (15 mL) and extracted with DCM (3 x 10 mL), Combined organic fractions were dried by phase separator and the mixture loaded onto silica for purification by flash chromatography. The desired compound A32 was isolated as a clear oil (144 mg, 29%); -NMR (400 MHz, DMSO-c/6): delta 7.78 (d, J = 8.0 Hz, 2H), 7.48 (d, J = 8.0 Hz, 2H), 4.56 (d, J = 5.0 Hz, 1 H), 4.12-4.00 (m, 2H), 3.65-3.57 (m, 1 H). 2.43 (s, 3H), 1 .69-1 .54 (m, 2H), 1 .00 (d, J = 6.0 Hz, 3H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, (S)-Butane-1,3-diol.

Reference£º
Patent; IMPERIAL INNOVATIONS LIMITED; SCHNEIDER, Michael; NEWTON, Gary; CHAPMAN, Katie; PERRIOR, Trevor; JARVIS, Ashley; LOW, Caroline; AQIL, Rehan; FISHER, Martin; BAYFORD, Melanie; CHAPMAN, Nicholas; MARTIN, Nicholas; REISINGER, Tifelle; NEGOITA-GIRAS, Gabriel; (260 pag.)WO2019/73253; (2019); 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

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4254-15-3,(S)-Propane-1,2-diol, as follows.4254-15-3

Compound M31:; To a solution of (S)-1 ,2-propandiol (5 mmol) in 5 ml_ of anhydrous CH2CI2 were added 2-methyl-1-butene (5.5 mmol) and BF3 etherate (0.5 mmol) at room temperature. The stirring was continued for another 24 h. The solvent was removed by vacuum, and the residue was purified by chromatograph on silica gel to afford intermediate (4 mmol, 80 percent yield) as oil. Then, to a suspension of this intermediate and imidazole (6 mmol) in 6 ml_ of anhydrous THF was added 4.8 mL of TBDMSCI (1 M in THF) at 0 0C. The solvent was removed by vacuum, and the residue was re-dissolved in Et2O. The heterogeneous mixture was filtered over a pad of Celite. The filtrate was washed with 1N HCI, water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed to give pure M31 (0.34 mmol, 85percent yield) as oil.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. (S)-Propane-1,2-diol, We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; UNIVERSITY OF CONNECTICUT; WO2006/44381; (2006); A2;,
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

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4254-15-3,(S)-Propane-1,2-diol, as follows.4254-15-3

Compound M31:; To a solution of (S)-1 ,2-propandiol (5 mmol) in 5 ml_ of anhydrous CH2CI2 were added 2-methyl-1-butene (5.5 mmol) and BF3 etherate (0.5 mmol) at room temperature. The stirring was continued for another 24 h. The solvent was removed by vacuum, and the residue was purified by chromatograph on silica gel to afford intermediate (4 mmol, 80 percent yield) as oil. Then, to a suspension of this intermediate and imidazole (6 mmol) in 6 ml_ of anhydrous THF was added 4.8 mL of TBDMSCI (1 M in THF) at 0 0C. The solvent was removed by vacuum, and the residue was re-dissolved in Et2O. The heterogeneous mixture was filtered over a pad of Celite. The filtrate was washed with 1N HCI, water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed to give pure M31 (0.34 mmol, 85percent yield) as oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4254-15-3, and friends who are interested can also refer to it.

Reference£º
Patent; UNIVERSITY OF CONNECTICUT; WO2006/44381; (2006); A2;,
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

4254-15-3,A common heterocyclic compound, 4254-15-3,(S)-Propane-1,2-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Under an atmosphere of argon, trifluoromethanesulfonic acid (485 muEpsilon; 822 mg; 5.47 mmol; 5.0 eq) was added dropwise at 0-5¡ãC (ice/brine bath) to a solution of l-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-(5- fluoroimidazol-l-yl)ethanone (400 mg ; 1.09 mmol) and (2S)-propane-l,2-diol (3.33 g; 43.8 mmol; 40.0 eq) in anhydrous toluene (3.0 mL). The resulting mixture was allowed to warm up to room temperature, then refluxed for 20h. Thereafter the reaction mixture was allowed to cool down to room temperature, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, the combined organic layers were – – dried (MgSO i) and concentrated to dryness in vacuo. The residue was purified by chromatography over silica gel, eluted with a mixture of dichloromethane/methanol (100:0 to 90: 10). Evaporation of the solvents in vacuo afforded 271 mg (54percent) of l-[[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-l,3-dioxolan-2- yl]methyl]-5-fluoro-imidazole (approx. 59:41 mixture of diastereoisomers) as a colourless solid. MS (ESI): 423.1 ([M+H]+)

The chemical industry reduces the impact on the environment during synthesis, 4254-15-3,(S)-Propane-1,2-diol,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; COQUERON, Pierre-Yves; BERNIER, David; GENIX, Pierre; MILLER, Ricarda; NAUD, Sebastien; WITTROCK, Sven; BRUNET, Stephane; KENNEL, Philippe; MEISSNER, Ruth; WACHENDORFF-NEUMANN, Ulrike; GOeRTZ, Andreas; (104 pag.)WO2018/60088; (2018); 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

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 538-58-9,1,5-Diphenylpenta-1,4-dien-3-one, as follows.538-58-9

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.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 538-58-9, We look forward to the emergence of more reaction modes in the future.

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

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 24621-61-2,(S)-Butane-1,3-diol, 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., 24621-61-2

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 24621-61-2, We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; DeLuca, Hector F.; Clagett-Dame, Margaret; Plum, Lori A.; Chiellini, Grazia; Grzywacz, Pawel; US2008/81800; (2008); 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

19132-06-0,Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials.19132-06-0,A new synthetic method of this compound is introduced below.

To a 500-mL, 3-necked-RBF (equipped with a H20-cooled refluxcondenser and an HC1 trap) was added (2s,3s)-(+)-2,3-butanediol (Aldrich; 15.00mL, 166 mmol) and CC14 (120 mL). SOC12, reagentplus (14.57 mL, 200 mmol)was then added drop wise via a syringe over a period of 20 mm and the resultingmixture was heated to 98C for 45 mm, then allowed to cool to rt. The reactionmixture was then cooled in an ice/H20 bath, MeCN (120 mL) and H20 (150 mL) were added followed by ruthenium(III) chloride (0.035 g, 0.166 mmol). Sodium periodate (53.4 g, 250 mmol) was then added slowly portion wise over 30 mm. The resulting biphasic brown mixture was stirred vigorously while allowed toreach rt for a period of 1.5 h (internal temperature never increased above rt). TLC (50% EtOAc in heptanes) showed complete conversion. The cmde mixture was then poured into ice H20 and extracted twice with 300 mL of Et20. The combined organic layers were washed once with 200 mL of sat. sodium bicarbonate, washed once with 200 mL of brine, dried over Na2504, andconcentrated by rotary evaporation to give (45,55)-4,5-dimethyl-1,3,2- dioxathiolane 2,2-dioxide (21.2 g, 139 mmol) as a red oil.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, (2S,3S)-Butane-2,3-diol.

Reference£º
Patent; AMGEN INC.; HARRINGTON, Paul E.; ASHTON, Kate; BROWN, Sean P.; KALLER, Matthew R.; KOHN, Todd J.; LANMAN, Brian Alan; LI, Kexue; LI, Yunxiao; LOW, Jonathan D.; MINATTI, Ana Elena; PICKRELL, Alexander J.; STEC, Markian M.; TAYGERLY, Joshua; (991 pag.)WO2018/183418; (2018); 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