Structure of 584-03-2
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 584-03-2 |
Formula : | C4H10O2 |
M.W : | 90.12 |
SMILES Code : | CCC(O)CO |
MDL No. : | MFCD00004570 |
InChI Key : | BMRWNKZVCUKKSR-UHFFFAOYSA-N |
Pubchem ID : | 11429 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H319 |
Precautionary Statements: | P264-P280-P305+P351+P338-P337+P313 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-mu-hydrotetracarbonyldiruthenium(II); cyclohexanone; at 150℃; for 0.5h; | 1,2-butanediol (2.14 mmol), cyclohexanone (4.12 mmol), 1(2.3 mol), and 2 (3.6 mol) were combined in a NMR tube adaptedwith a J. Young valve and degassed by 5 ftp cycles. The mixture washeated to 150C for 19.5 h, after which the tube was cooled to rt,and a13C NMR spectrum recorded. The gas phase in the headspacewas analyzed by GC-TCD, and an aliquot of the liquid was dissolvedin DMSO-d6and the1H NMR spectrum recorded. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen;dichloro[(R)-N-bis(3,4-difluorophenyl)phosphino-N-methyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine](triphenylphosphine)ruthenium; In methanol; at 20℃; under 16274.9 Torr; for 6h;Conversion of starting material; | Complex 5A-j from Example 12 (2.8 mg; 0.0025 mmol; 0.005 equiv) and 1hydroxy-2-butanone (45 muL; 0.5 mmol) were placed in a reaction vessel, which was pressurized with argon and vented five times. Argon-degassed methanol (5 mL) was added and the reaction mixture was pressurized with argon and vented five times and then pressurized to 20.7 barg (300 psig) with hydrogen and stirred at ambient temperature for 6 hours. The vessel was vented, then pressurized with argon and vented five times. Analysis of the reaction mixture by chiral GC indicated 81.9percent conversion to 1,2-butanediol. The solvent was stripped and the residue was converted to the diacetate using acetic anhydride (0.14 mL; 1.5 mmol; 3 equiv) and triethylamine (0.28 mL; 2.0 mmol; 4 equiv) with a catalytic amount of DMAP in 2.5 mL of dichloromethane. Assay of the 1,2-diacetoxybutane thus produced indicated 87.4percent ee of the (R)-enantiomer according to chiral GC analysis. Chiral GC [30 m.x.0.25 mm Cyclosil-B (JW Scientific), 0.25 mum film thickness, 100° C. isothermal]: tR=7.23 min (1-hydroxy-2-butanone), tR=13.8, 14.1 min (1,2-butanediol), tR 16.85 min [(S)-1,2-diacetoxybutane], tR=17.75 min [(R)-1,2-diacetoxybutane]. | |
With hydrogen;dichloro[(R)-N-bis(3,4-difluorophenyl)phosphino-N-methyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine](triphenylphosphine)ruthenium; In ethanol; at 20℃; under 16274.9 Torr; for 6h;Conversion of starting material; | Complex 5A-j from Example 12 (2.8 mg; 0.0025 mmol; 0.005 equiv) and 1hydroxy-2-butanone (45 muL; 0.5 mmol) were placed in a reaction vessel, which was pressurized with argon and vented five times. Argon-degassed ethanol (5 mL) was added and the reaction mixture was pressurized with argon and vented five times and then pressurized to 20.7 barg (300 psig) with hydrogen and stirred at ambient temperature for 6 hours. The vessel was vented, then pressurized with argon and vented five times. Analysis of the reaction mixture by chiral GC indicated 93.4percent conversion to 1,2-butanediol. The solvent was stripped and the residue was converted to the diacetate using acetic anhydride (0.14 mL; 1.5 mmol; 3 equiv) and triethylamine (0.28 mL; 2.0 mmol; 4 equiv) with a catalytic amount of DMAP in 2.5 mL of dichloromethane. Assay of the 1,2-diacetoxybutane thus produced indicated 88.8percent ee of the (R)-enantiomer according to chiral GC analysis. | |
With hydrogen;dichloro[(R)-N-bis(3,4-dichlorophenyl)phosphino-N-methyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine](triphenylphosphine)ruthenium; In methanol; at 20℃; under 16274.9 Torr; for 6h;Conversion of starting material; | Complex 5A-k from Example 13 (3.0 mg; 0.0025 mmol; 0.005 equiv) and 1hydroxy-2-butanone (45 muL; 0.5 mmol) were placed in a reaction vessel, which was pressurized with argon and vented five times. Argon-degassed methanol (5 mL) was added and the reaction mixture was pressurized with argon and vented five times and then pressurized to 20.7 barg (300 psig) with hydrogen and stirred at ambient temperature for 6 hours. The vessel was vented, then pressurized with argon and vented five times. Analysis of the reaction mixture by chiral GC indicated 65.6percent conversion to 1,2-butanediol. The solvent was stripped and the residue was converted to the diacetate using acetic anhydride (0.14 mL; 1.5 mmol; 3 equiv) and triethylamine (0.28 mL; 2.0 mmol; 4 equiv) with a catalytic amount of DMAP in 2.5 mL of dichloromethane. Assay of the 1,2-diacetoxybutane thus produced indicated 84.6percent ee of the (R)-enantiomer according to chiral GC analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1% platinum on charcoal; oxygen; In water; at 100℃; under 2250.23 Torr; for 24h; | Reactions were carried out using a Radley?s low pressure glass reactor (50 ml). A butanediol in water (20 ml, 0.6 M) and the catalyst(butanediol/metal ratio2000) were added into the reactor,which was then pressurized with oxygen (3 bar). The reaction mixture was heated to 100 C for 24 h under constant stirring(1000 rpm), then cooled to room temperature and analyzed. 1H-NMR spectroscopy was used for product identification; spectrawere acquired over a 16 scan period using a Bruker 400 MHz DPXsystem with a 5 mm auto tune broadband probe. All samples were prepared as dilute solutions in D2O. Carbon mass balances were calculated and were between 96 and 104percent. Blank reactions have also been carried out with no oxidation activity detected in the absence of catalyst or with the KB-B carbon support. | |
45%Spectr.; 55%Spectr. | With oxygen; In water; at 100℃; under 2250.23 Torr; for 24h; | General procedure: (0017) Reactions were carried out using a Radley's low pressure glass reactor (50ml). A butanediol in water (20ml, 0.6M) and the catalyst (butanediol/metal ratio=2000) were added into the reactor, which was then pressurized with oxygen (3bar). The reaction mixture was heated to 100°C for 24h under constant stirring (1000rpm), then cooled to room temperature and analyzed. 1H NMR spectroscopy was used for product identification; spectra were acquired over a 16 scan period using a Bruker 400MHz DPX system with a 5mm auto tune broadband probe. All samples were prepared as dilute solutions in D2O. Carbon mass balances were calculated and were between 96 and 104percent. Blank reactions have also been carried out with no oxidation activity detected in the absence of catalyst or with the KB-B carbon support. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Au-Pd/carbon catalyst; oxygen; In water; at 100℃; under 2250.23 Torr; for 24h; | Reactions were carried out using a Radley?s low pressure glass reactor (50 ml). A butanediol in water (20 ml, 0.6 M) and the catalyst(butanediol/metal ratio2000) were added into the reactor,which was then pressurized with oxygen (3 bar). The reaction mixture was heated to 100 C for 24 h under constant stirring(1000 rpm), then cooled to room temperature and analyzed. 1H-NMR spectroscopy was used for product identification; spectrawere acquired over a 16 scan period using a Bruker 400 MHz DPXsystem with a 5 mm auto tune broadband probe. All samples were prepared as dilute solutions in D2O. Carbon mass balances were calculated and were between 96 and 104percent. Blank reactions have also been carried out with no oxidation activity detected in the absence of catalyst or with the KB-B carbon support. | |
6%Spectr.; 46%Spectr.; 45%Spectr. | With oxygen; In water; at 100℃; under 2250.23 Torr; for 24h; | General procedure: (0017) Reactions were carried out using a Radley's low pressure glass reactor (50ml). A butanediol in water (20ml, 0.6M) and the catalyst (butanediol/metal ratio=2000) were added into the reactor, which was then pressurized with oxygen (3bar). The reaction mixture was heated to 100°C for 24h under constant stirring (1000rpm), then cooled to room temperature and analyzed. 1H NMR spectroscopy was used for product identification; spectra were acquired over a 16 scan period using a Bruker 400MHz DPX system with a 5mm auto tune broadband probe. All samples were prepared as dilute solutions in D2O. Carbon mass balances were calculated and were between 96 and 104percent. Blank reactions have also been carried out with no oxidation activity detected in the absence of catalyst or with the KB-B carbon support. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; In water; at 100℃; under 2250.23 Torr; for 24h; | Reactions were carried out using a Radley?s low pressure glass reactor (50 ml). A butanediol in water (20 ml, 0.6 M) and the catalyst(butanediol/metal ratio2000) were added into the reactor,which was then pressurized with oxygen (3 bar). The reaction mixture was heated to 100 C for 24 h under constant stirring(1000 rpm), then cooled to room temperature and analyzed. 1H-NMR spectroscopy was used for product identification; spectrawere acquired over a 16 scan period using a Bruker 400 MHz DPXsystem with a 5 mm auto tune broadband probe. All samples were prepared as dilute solutions in D2O. Carbon mass balances were calculated and were between 96 and 104percent. Blank reactions have also been carried out with no oxidation activity detected in the absence of catalyst or with the KB-B carbon support. | |
7%Spectr.; 11%Spectr.; 28%Spectr.; 54%Spectr. | With oxygen; In water; at 100℃; under 2250.23 Torr; for 24h; | General procedure: (0017) Reactions were carried out using a Radley's low pressure glass reactor (50ml). A butanediol in water (20ml, 0.6M) and the catalyst (butanediol/metal ratio=2000) were added into the reactor, which was then pressurized with oxygen (3bar). The reaction mixture was heated to 100°C for 24h under constant stirring (1000rpm), then cooled to room temperature and analyzed. 1H NMR spectroscopy was used for product identification; spectra were acquired over a 16 scan period using a Bruker 400MHz DPX system with a 5mm auto tune broadband probe. All samples were prepared as dilute solutions in D2O. Carbon mass balances were calculated and were between 96 and 104percent. Blank reactions have also been carried out with no oxidation activity detected in the absence of catalyst or with the KB-B carbon support. |
7%Spectr.; 11%Spectr.; 28%Spectr.; 54%Spectr. | With oxygen; In water; at 100℃; under 2250.23 Torr; for 24h; | General procedure: (0017) Reactions were carried out using a Radley's low pressure glass reactor (50ml). A butanediol in water (20ml, 0.6M) and the catalyst (butanediol/metal ratio=2000) were added into the reactor, which was then pressurized with oxygen (3bar). The reaction mixture was heated to 100°C for 24h under constant stirring (1000rpm), then cooled to room temperature and analyzed. 1H NMR spectroscopy was used for product identification; spectra were acquired over a 16 scan period using a Bruker 400MHz DPX system with a 5mm auto tune broadband probe. All samples were prepared as dilute solutions in D2O. Carbon mass balances were calculated and were between 96 and 104percent. Blank reactions have also been carried out with no oxidation activity detected in the absence of catalyst or with the KB-B carbon support. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; In water; at 100℃; under 2250.23 Torr; for 24h; | Reactions were carried out using a Radley?s low pressure glass reactor (50 ml). A butanediol in water (20 ml, 0.6 M) and the catalyst(butanediol/metal ratio2000) were added into the reactor,which was then pressurized with oxygen (3 bar). The reaction mixture was heated to 100 C for 24 h under constant stirring(1000 rpm), then cooled to room temperature and analyzed. 1H-NMR spectroscopy was used for product identification; spectrawere acquired over a 16 scan period using a Bruker 400 MHz DPXsystem with a 5 mm auto tune broadband probe. All samples were prepared as dilute solutions in D2O. Carbon mass balances were calculated and were between 96 and 104percent. Blank reactions have also been carried out with no oxidation activity detected in the absence of catalyst or with the KB-B carbon support. |