Conditions | Yield |
---|---|
With RuBr2[(S,S)-2,4-bis(diphenylphosphino)pentane](2-aminomethyl-3,5-dimethylpyridine); potassium tert-butylate; hydrogen In ethanol at 40℃; under 7600.51 Torr; for 19h; Reagent/catalyst; Inert atmosphere; Autoclave; | A 100% B n/a |
With dimethylsulfide borane complex; diphenyl-N-(3-pyridylmethyl)prolinol N-oxide In tetrahydrofuran for 5h; Heating; | A n/a B 99% |
With borane-THF; (R)-1-(1'-amino-1'-phenylmethyl)cyclopentanol In tetrahydrofuran at 30℃; for 2h; Title compound not separated from byproducts; | A 98% B n/a |
Conditions | Yield |
---|---|
With (S)-2-amino-1,1,3-triphenylpropan-1-ol borane In tetrahydrofuran at 30℃; | 100% |
With dimethylsulfide borane complex; (S)-chiral amino alcohol; aluminum ethoxide In tetrahydrofuran at 20℃; Reduction; | 100% |
With (S)-diphenylprolinol; dimethylsulfide borane complex In tetrahydrofuran at 20℃; | 100% |
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; (R,S)-2-OH-3,5-Cl2-C6H2-SO2-NH-CH(CH2Ph)-CH(Ph)OH In tetrahydrofuran at 0℃; for 12h; | 100% |
In tetrahydrofuran; hexane at -20℃; for 3h; Product distribution / selectivity; | 60% |
acetophenone
(E)-benzalacetone
A
(S)-1-phenylethanol
B
(R)-1-phenylethanol
Conditions | Yield |
---|---|
With Triethoxysilane; (S,S,S,S)-N,N'-di(α-phenylethyl)cyclohexane-1,2-diamine; diethylzinc In toluene at 20℃; for 18h; Title compound not separated from byproducts.; | A n/a B 100% |
With polymethylhydrosiloxane; (S,S,S,S)-N,N'-di(α-phenylethyl)cyclohexane-1,2-diamine; diethylzinc In toluene at 20℃; for 24h; Title compound not separated from byproducts.; | A n/a B 90% |
Conditions | Yield |
---|---|
With Candida albicans CCT 0776 In water at 30℃; for 360h; Time; Enzymatic reaction; enantioselective reaction; | 100% |
With C48H48N2O4Ru2 In benzene at 30℃; for 20h; Irradiation; Darkness; optical yield given as %ee; | 99.9% |
Stage #1: (S)-1-phenylethanol With azodicarboxylic acid bis(2-methoxyethyl) ester; 4-diphenylphosphanobenzoic acid In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 20℃; stereospecific reaction; | 90% |
1-Phenylethanol
(R)-1-phenylethanol
Conditions | Yield |
---|---|
With alcohol dehydrogenase from Thermoanaerobium brockii; NADH-specific (R)-selective-ADH; YcnD-oxidoreductase at 30℃; for 6h; pH=7.5; aq. buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantiospecific reaction; | 99% |
In water at 30℃; for 24h; Geotrichum Candidum IFQ 5767; | 96% |
With cells of Geotrichum candidum IFO 5767 In water at 30℃; for 24h; | 96% |
(R)-1-phenyl-1-(trichlorosilyl)ethane
(R)-1-phenylethanol
Conditions | Yield |
---|---|
With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; methanol for 16h; | 99% |
With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; methanol; water at 20℃; for 12h; enantioselective reaction; | 37% |
With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; methanol for 10h; Ambient temperature; Yield given; |
(R)-1-phenethyl acetate
(R)-1-phenylethanol
Conditions | Yield |
---|---|
With water; potassium carbonate In methanol at 20℃; optical yield given as %ee; | 99% |
With methanol; sodium hydroxide for 1h; | 99% |
With methanol; oxo[hexa(trifluoroacetato)]tetrazinc for 18h; Reflux; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In hexane at -35℃; for 3h; | 99% |
Stage #1: dimethyl zinc(II) With (1S,2S,4R)-1,3,3-trimethyl-2-[(R)-2-(6-phenylpyridin-2-yl)phenyl]bicyclo-[2.2.1]heptan-2-ol In toluene at 0 - 20℃; Inert atmosphere; Stage #2: benzaldehyde In toluene at 0℃; for 96h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Stage #1: dimethyl zinc(II); benzaldehyde With (2R,3S,3aS,4aR,6R,8aS)-2-isopropyl-6,9,9-trimethyl-3-phenyldecahydro-4aH-pyrrolo[2,1-b][1,3]benzoxazin-3-ol In hexane; toluene at -20 - 20℃; for 30h; Inert atmosphere; Stage #2: With ammonium chloride In hexane; water; toluene Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 96% |
(S)-1-tert-butyl 3-((R)-1-phenylethyl) 2-methyl-2-allylmalonate
A
(R)-1-phenylethanol
B
(S)-2-((tert-butoxy)carbonyl)-2-methylpent-4-enoic acid
Conditions | Yield |
---|---|
With water; potassium hydroxide In methanol at 20℃; for 24h; | A n/a B 98% |
α-bromoacetophenone
A
(R)-1-phenylethanol
B
(S)-2-bromo-1-phenylethanol
Conditions | Yield |
---|---|
With sodium formate; cetyltrimethylammonim bromide; sodium dodecyl-sulfate; (R,R)-TsDPEN; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 28℃; for 1h; | A 3 % Spectr. B 97% |
Conditions | Yield |
---|---|
Stage #1: phenylacetylene With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water In methanol at 110℃; for 6h; Stage #2: With C26H26ClN2O2RhS; water; sodium formate In methanol at 30℃; for 5h; | 97% |
Stage #1: phenylacetylene With formic acid at 100℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: With pentamethylcyclopentadienyl*RhCl[(S,S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]; water; sodium hydroxide at 20 - 40℃; for 3h; pH=7; enantioselective reaction; | 87% |
With iron(III) chloride; sodium formate In water at 40℃; for 24h; optical yield given as %ee; | 86% |
(R)-1-phenylethanol
Conditions | Yield |
---|---|
With water In tetrahydrofuran for 12h; Reagent/catalyst; Reflux; | 97% |
(R,R)-(-)-1,6-bis(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol
acetophenone
A
(S)-1-phenylethanol
B
(R)-1-phenylethanol
Conditions | Yield |
---|---|
With 1,2-diaminoethane-bisborane In solid Product distribution; enantioselective reduction of var. ketones in optically active host compounds with a BH3-ethylenediamine complex in the solid state; | A n/a B 96% |
Conditions | Yield |
---|---|
With (Sa)-2'-((S)-hydroxy(phenyl)methyl)-[1,1'-binaphthalen]-2-ol In tetrahydrofuran; diethyl ether at 0℃; for 1.5h; Catalytic behavior; Solvent; Temperature; enantioselective reaction; | 96% |
1-Phenylethanol
4-chlorophenyl acetate
A
(S)-1-phenylethanol
B
(R)-1-phenylethanol
C
(R)-1-phenethyl acetate
Conditions | Yield |
---|---|
With Novozym 435; potassium tert-butylate; sodium carbonate; [2,3,4,5-Ph4(η5-C4CNH(i-Pr))]Ru(CO)2Cl In toluene at 25℃; for 42h; | A n/a B n/a C 95% |
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium tert-butylate; sodium carbonate In toluene at 60℃; for 48h; Inert atmosphere; Schlenk technique; Enzymatic reaction; Overall yield = 70 %Spectr.; Optical yield = 40 %ee; enantioselective reaction; |
(R)-1-phenylethanol
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; methanol at 0 - 20℃; for 1.5h; | 94% |
1-phenylethyl acetate
A
(R)-1-phenylethanol
B
benzyl (1S,2R)-[(2-acetylamino)cyclopentyl]carbamate
Conditions | Yield |
---|---|
With triethylamine In tert-butyl methyl ether at 50℃; for 216h; Inert atmosphere; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; | A n/a B 94% |
Conditions | Yield |
---|---|
With Aspergillus niger MTCC-404 at 35℃; for 24h; aq. phosphate buffer; Microbiological reaction; Closed tube; optical yield given as %ee; | A 93% B n/a |
Stage #1: ethylbenzene With 1-(tert-butoxycarbonyl)-L-proline; [(2R,2’R)-1,1’-bis((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)-2,2’-bipyrrolidineMnII(OTf)2]; dihydrogen peroxide at -40℃; Stage #2: In acetonitrile enantioselective reaction; | A 39% B n/a |
With calcium sulfite; recombinant peroxygenase from Agrocybe aegerita; sulfite oxidase from Arabidopsis thaliana In aq. phosphate buffer at 30℃; pH=7; Catalytic behavior; Enzymatic reaction; enantioselective reaction; | A 155 mg B 23% |
1-phenylethyl propanoate
2-heptylamine
A
(R)-1-phenylethanol
C
(R)-1-phenylethyl propionate
D
(S)-1-phenylethyl propionate
Conditions | Yield |
---|---|
With hydrogen; lipase B from Candida antarctica In toluene at 70℃; under 750.075 Torr; for 48h; Resolution of racemate; Enzymatic reaction; | A 47% B 93% C n/a D n/a |
1-phenylethyl propanoate
2-heptylamine
B
(R)-1-phenylethanol
C
(R)-1-phenylethyl propionate
D
(S)-1-phenylethyl propionate
Conditions | Yield |
---|---|
With hydrogen; lipase B from Candida antarctica In toluene at 70℃; under 750.075 Torr; for 48h; Resolution of racemate; Enzymatic reaction; | A 93% B 47% C n/a D n/a |
1-phenylethyl propanoate
RS-mexiletine
A
(R)-1-phenylethanol
C
(S)-1-phenylethyl propionate
Conditions | Yield |
---|---|
With hydrogen; lipase B from Candida antarctica In toluene at 70℃; under 750.075 Torr; for 48h; Resolution of racemate; Enzymatic reaction; | A 46% B 93% C n/a |
Isopropenyl acetate
1-Phenylethanol
A
(S)-1-phenylethanol
B
(R)-1-phenylethanol
C
(R)-1-phenethyl acetate
Conditions | Yield |
---|---|
With Candida antarctica lipase B; dicarbonyl(chloro)(η5-pentaphenylcyclopentadienyl)ruthenium(II); potassium tert-butylate; sodium carbonate In tetrahydrofuran; toluene at 20℃; for 3h; | A n/a B n/a C 92% |
With Pseudomonas cepacia lipase In diethyl ether at 40℃; for 24h; Enzymatic reaction; enantioselective reaction; | A n/a B n/a C 9% |
With Novozym 435; potassium tert-butylate; sodium carbonate; [2,3,4,5-Ph4(η5-C4CNH(i-Pr))]Ru(CO)2Cl In toluene at 25℃; for 30h; Product distribution; Further Variations:; Reagents; Solvents; reaction times; |
bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct
benzaldehyde
(R)-1-phenylethanol
Conditions | Yield |
---|---|
In tetrahydrofuran at 5℃; for 1h; Product distribution / selectivity; | 92% |
Conditions | Yield |
---|---|
With (S,S)-2,3-O-isopropylidene-1,1,4,4-tetraphenylthreitol In hexane at 20℃; for 72h; | A n/a B 90% |
With Candida antarctica lipase B; 1-(10-carboxydecyl)-3-methylimidazolium hexafluorophosphate; diisopropyl-carbodiimide In acetone at 40℃; for 14h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A 51% B 32% |
Stage #1: 1-Phenylethanol With Novozym 435(R); 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 35℃; under 100 Torr; for 96h; Stage #2: With ethanol at 35℃; for 24h; Further stages.; | A n/a B 22.5% |
<2S-(2α(S*),3aα,4α,7α,7aα)>-2,3,3a,4,5,6,7,7a-Octahydro-7,8,8-trimethyl-2-(1-phenylethoxy)-4,7-methanobenzofuran
(R)-1-phenylethanol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; triethylamine In methanol for 1h; Ambient temperature; | 90% |
1-styrenyloxytrimethylsilane
(R)-1-phenylethanol
Conditions | Yield |
---|---|
Stage #1: 1-styrenyloxytrimethylsilane With tri-tert-butyl phosphine; C52H54; hydrogen; bis(pentafluorophenyl)borohydride In 1,3,5-trimethyl-benzene; pentane at 50℃; under 30003 Torr; for 24h; Inert atmosphere; Sealed tube; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; 1,3,5-trimethyl-benzene; pentane at 20℃; for 1h; Reagent/catalyst; Concentration; Solvent; enantioselective reaction; | 90% |
Multi-step reaction with 2 steps 1: C52H58; tri-tert-butyl phosphine; hydrogen / hexane / 24 h / 30003 Torr 2: tetrabutyl ammonium fluoride / toluene; pentane; tetrahydrofuran / 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: bis(pentafluorophenyl)borohydride; C52H58; tri-tert-butyl phosphine; hydrogen / toluene; pentane / 24 h / 50 °C / 30003 Torr / Autoclave 2: tetrabutyl ammonium fluoride / toluene; pentane; tetrahydrofuran / 0.5 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With triisopropoxytitanium(IV) chloride; (Sa)-2'-((S)-hydroxy(phenyl)methyl)-[1,1'-binaphthalen]-2-ol In diethyl ether; hexane at -20℃; for 0.166667h; Reagent/catalyst; enantioselective reaction; | 90% |
Conditions | Yield |
---|---|
With Candida albicans CCT 0776 In water at 30℃; for 144h; Time; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A 89% B 11% |
With Sphingomonas paucimobilis NCIMB 8195 In water; N,N-dimethyl-formamide for 144h; | A 81% B 14% |
With Candida albicans CCT 0776 whole cells at 28℃; for 2.5h; pH=7; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; | A 48% B 50% |
vinyl acetate
1-Phenylethanol
A
(S)-1-phenylethanol
B
(R)-1-phenylethanol
C
(R)-1-phenethyl acetate
Conditions | Yield |
---|---|
With Novozym 435; potassium tert-butylate; sodium carbonate; [2,3,4,5-Ph4(η5-C4CNH(i-Pr))]Ru(CO)2Cl In toluene at 25℃; for 96h; | A n/a B n/a C 89% |
With lipase PS from Burkholderia cepacia at 35℃; Ionic liquid; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; | A n/a B n/a C 58% |
With IL1; Lipase PS-C In di-isopropyl ether at 35℃; for 2h; Product distribution; Enzyme kinetics; Kinetics; Further Variations:; Reagents; time; | A n/a B n/a C 39% |
(R)-1-phenylethanol
(S)-chlorofluoroacetic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Esterification; | 100% |
Conditions | Yield |
---|---|
chiral ruthenium(II)(NO+)Cl(salen) In chlorobenzene at 20℃; for 24h; Irradiation; | 100% |
4-methyleneoxetan-2-one
(R)-1-phenylethanol
(R)-1-phenylethyl acetoacetate
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran at 20℃; | 100% |
(R)-1-phenylethanol
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; | 99% |
Conditions | Yield |
---|---|
With oxalyl dichloride; 2,3-bis(4-methoxyphenyl)cyclopropenone In dichloromethane at 30℃; for 1h; Inert atmosphere; optical yield given as %ee; | 98% |
With thionyl chloride In dichloromethane at 0 - 50℃; for 3h; Inert atmosphere; | 66% |
With thionyl chloride In dichloromethane at 0 - 50℃; Inert atmosphere; | 66% |
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran for 20h; Alkylation; Heating; | 98% |
5-methyl-1,10-phenanthroline
3-methoxy-1-iodobenzene
(R)-1-phenylethanol
Conditions | Yield |
---|---|
With CuI; caesium carbonate In toluene | 98% |
(R)-1-phenylethanol
N,N-Dimethylthiocarbamoyl chloride
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran; mineral oil at 25℃; for 1h; Inert atmosphere; | 98% |
(R)-1-phenylethanol
Ethyl oxalyl chloride
ethyl (R)-1-phenylethyl oxalate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; | 97% |
With pyridine In dichloromethane at 20℃; | 97% |
(R)-1-phenylethanol
Methacryloyl chloride
(R)-α-methylbenzyl methacrylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 24h; | 97% |
(R)-1-phenylethanol
1,1'-carbonyldiimidazole
(R)-1-phenylethyl 1H-imidazole-1-carboxylate
Conditions | Yield |
---|---|
In ethyl acetate for 20h; Reflux; Inert atmosphere; | 96% |
In ethyl acetate for 20h; Inert atmosphere; Reflux; | 96% |
In dichloromethane at 0 - 20℃; for 17h; Inert atmosphere; | 90% |
In dichloromethane at 20℃; for 0.5h; |
4-bromo-2-methyl-benzoic acid tert-butyl ester
(R)-1-phenylethanol
tert-butyl 3-methyl-2'-[(1R)-1-hydroxyethyl]biphenyl-4-carboxylate
Conditions | Yield |
---|---|
Stage #1: (R)-1-phenylethanol With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 50℃; for 1h; Cooling with ice; Inert atmosphere; Stage #2: With Triisopropyl borate In hexane at 20 - 40℃; for 2h; Inert atmosphere; Stage #3: 4-bromo-2-methyl-benzoic acid tert-butyl ester With potassium phosphate; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; water at 20 - 65℃; for 2.5h; Suzuki Coupling; Inert atmosphere; | 95.5% |
3-ethoxy-2-methylacrolein
(R)-1-phenylethanol
(E)-(1'R)-2-Methyl-3-(1'-phenylethoxy)-propenal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid under 1 Torr; | 95% |
With toluene-4-sulfonic acid under 0.05 Torr; for 3h; Ambient temperature; | 93% |
Hazard Codes : Xn (Harmful)
Risk Statements : 22-38-41-36/37/38 (Harmful if swallowed; Irritating to the skin; Risk of serious damage to eyes; Irritating to eyes, respiratory system and skin)
Safety Statements : 26-39-37/39 (In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; Wear eye/face protection; Wear suitable gloves and eye/face protection)
RIDADR : UN 2937 6.1/PG 3
WGK Germany : 3
HazardClass : 6.1
PackingGroup : III
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