Conditions | Yield |
---|---|
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 0.25h; Reduction; | 99% |
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; Reflux; | 99% |
With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran at 20℃; | 98% |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With sulfuric acid In water at 120℃; | 98% |
With sulfuric acid at 100℃; for 48h; Darkness; | 143.7 mg |
A
(R)-2-amino-3-phenylpropanol
B
(R)-3-phenylpropane-1,2-diamine
Conditions | Yield |
---|---|
With hydrogenchloride; methanol; water; hydrogen; 5% palladium over charcoal at 35℃; under 6750.68 - 22502.3 Torr; for 43h; | A 91% B 6% |
(R)-4-(phenylmethyl)-2-oxazolidinone
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With ammonium bromide; 3-azapentane-1,5-diamine at 90℃; for 5h; Microwave irradiation; | 84% |
9H-fluoren-9-ylmethyl (R)-<1-(hydroxymethyl)-2-phenylethyl>carbamate
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With piperidine In dichloromethane for 1h; Ambient temperature; | 82% |
D-phenylalanine methyl ester
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 0 - 10℃; for 1h; Temperature; Solvent; | 81% |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With ammonium formate; palladium on activated charcoal In methanol for 2h; Heating; | 80% |
(+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With hydrazine hydrate In acetonitrile for 4h; Heating; | 73% |
rac-phenylalaninol
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Stage #1: rac-phenylalaninol With O,O'-dibenzoyl-L-tartaric acid In acetone at 25℃; for 6h; Stage #2: With potassium hydroxide In dichloromethane | 52% |
(L)-phenylalanine ethyl ester hydrochloride
A
L-Phenylalaninol
B
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere; optical yield given as %ee; | A 27% B n/a |
D-phenylalanine ethyl ester
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran |
rac-phenylalaninol
(2R)-mandelamide
A
L-Phenylalaninol
B
(R)-2-amino-3-phenylpropanol
C
(R)-Mandelic Acid
D
(R)-N-<(S)-1-benzyl-2-hydroxyethyl>mandelamide
Conditions | Yield |
---|---|
With Alcaligenes PA In water at 25℃; pH=10; |
ethyl 2-(hydroxyimino)-3-phenylpropanoate
A
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 80 percent / NaBH4; I2 / tetrahydrofuran / 4 h / Heating 2.1: dibenzoyl-L-tartaric acid / acetone / 6 h / 25 °C 2.2: 52 percent / aq. KOH / CH2Cl2 View Scheme |
Boc-D-Phe-OH
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: BH3*THF 2: H3O(1+) View Scheme |
Hydroxymethyl-((R)-1-hydroxymethyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 82 percent / NaOH / methanol; H2O / Ambient temperature 2: H3O(1+) View Scheme |
(1S,2S)-2-amino-1-phenyl-1,3-diol
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 93 percent / xylene / 2 h / Heating 2: 1.) SOCl2, 2.) LiBr / 1.) CHCl3, 8 h, 2.) Me2CO, 6 h 3: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: 93 percent / xylene / 2 h / Heating 2: 60 percent / SOCl2, Et3N / CH2Cl2 / 1 h / 0 °C 3: 60 percent / LiBr, PTSA / acetonitrile / 2 h / Ambient temperature 4: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 5: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme |
(1S,2S)-1-phenyl-2-phthalimido-propane-1,3-diol
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) SOCl2, 2.) LiBr / 1.) CHCl3, 8 h, 2.) Me2CO, 6 h 2: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 60 percent / SOCl2, Et3N / CH2Cl2 / 1 h / 0 °C 2: 60 percent / LiBr, PTSA / acetonitrile / 2 h / Ambient temperature 3: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme |
2-((4S,5S)-2-Oxo-4-phenyl-2λ4-[1,3,2]dioxathian-5-yl)-isoindole-1,3-dione
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 60 percent / LiBr, PTSA / acetonitrile / 2 h / Ambient temperature 2: 80 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 73 percent / NH2NH2*H2O / acetonitrile / 4 h / Heating View Scheme |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2.) KF, NaHCO3, 30percent H2O2 / 1.) THF, RT, 24 h, 2.) THF, methanol, RT, 48 h 2: 80 percent / HCO2NH4 / 10percent Pd-C / methanol / 2 h / Heating View Scheme |
(-)-(R)-(N-9-fluorenylmethoxycarbonyl)phenylalaninal
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / sodium borohydride / tetrahydrofuran / 2 h / 0 °C 2: 82 percent / piperidine / CH2Cl2 / 1 h / Ambient temperature View Scheme |
(R)-dibenzyl 1-(1-hydroxy-3-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With hydrogen; nickel In methanol; acetic acid at 25℃; under 3102.97 Torr; for 20h; |
(R)-2-nitro-3-phenylpropan-1-ol
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With sulfuric acid; zinc In water |
rac-phenylalaninol
A
L-Phenylalaninol
B
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With chiral stationary phase including isopropyl-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 20℃; Purification / work up; | |
With C45H31O4P In aq. phosphate buffer; chloroform at 6℃; for 16h; Reagent/catalyst; Sealed tube; Resolution of racemate; | |
With (S)-(+)-3,3'-diphenyl-2,2'-bi-1-naphthol hydrogen phosphate In aq. phosphate buffer; chloroform; water at 6℃; for 16h; pH=5; Reagent/catalyst; enantioselective reaction; | A n/a B n/a |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene; di[(η-1,2,5,6)-1,5-cyclooctadiene] rhodium hexafluoroantimonate; hydrogen / dichloromethane / 12 h / 20 °C / Autoclave 2: sulfuric acid / 48 h / 100 °C / Darkness View Scheme | |
Multi-step reaction with 2 steps 1: di[(η-1,2,5,6)-1,5-cyclooctadiene] rhodium hexafluoroantimonate; hydrogen; (R)-1-[(Sp)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine / dichloromethane / 4 h / 20 °C / 22801.5 Torr / Autoclave 2: sulfuric acid / 48 h / 100 °C / Darkness View Scheme | |
Multi-step reaction with 3 steps 1: (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene; di[(η-1,2,5,6)-1,5-cyclooctadiene] rhodium hexafluoroantimonate; hydrogen / ethyl acetate / 4 h / 20 °C / 22801.5 Torr / Autoclave 2: sodium tetrahydroborate 3: sulfuric acid / 48 h / 100 °C / Darkness View Scheme | |
Multi-step reaction with 3 steps 1: (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene; di[(η-1,2,5,6)-1,5-cyclooctadiene] rhodium hexafluoroantimonate; hydrogen / dichloromethane / 4 h / 20 °C / Autoclave 2: sodium tetrahydroborate 3: sulfuric acid / 48 h / 100 °C / Darkness View Scheme | |
Multi-step reaction with 3 steps 1: di[(η-1,2,5,6)-1,5-cyclooctadiene] rhodium hexafluoroantimonate; hydrogen; (R)-1-[(Sp)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine / dichloromethane / 4 h / 20 °C / 22801.5 Torr / Autoclave 2: sodium tetrahydroborate 3: sulfuric acid / 48 h / 100 °C / Darkness View Scheme |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate 2: sulfuric acid / 48 h / 100 °C / Darkness View Scheme |
di-tert-butyl dicarbonate
(R)-2-amino-3-phenylpropanol
N-tert-butoxycarbonyl-D-Phenylalaninol
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; | 100% |
In ethanol at 30℃; for 0.0166667h; | 99% |
In chloroform at 0 - 20℃; Substitution; | 95% |
(R)-2-amino-3-phenylpropanol
chloroacetyl chloride
2-chloro-N-(1-hydroxymethyl-2-phenyl-ethyl)-acetamide
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 25℃; | 100% |
tert-butyldicarbonate
(R)-2-amino-3-phenylpropanol
N-tert-butoxycarbonyl-D-Phenylalaninol
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; water at 20℃; for 24h; | 100% |
(R)-2-amino-3-phenylpropanol
1-chloro-2(R)-amino-phenylpropane hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide at 120℃; for 2h; | 99% |
(R)-2-amino-3-phenylpropanol
methyl chloroformate
R-(+)-N,O-bis(methoxycarbonyl)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With pyridine In chloroform at 20℃; for 14h; Condensation; | 99% |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
In methanol at 20℃; for 3h; Inert atmosphere; optical yield given as %de; | 99% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane 0 deg C, 30 min; 23 deg C, 2 h; | 97% |
carbon dioxide
(R)-2-amino-3-phenylpropanol
(R)-4-(phenylmethyl)-2-oxazolidinone
Conditions | Yield |
---|---|
With triethylamine; chlorophosphoric acid diphenyl ester In acetonitrile at -40 - 25℃; | 97% |
Stage #1: carbon dioxide; (R)-2-amino-3-phenylpropanol With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.75h; Stage #2: With tributylphosphine; di-tert-butyl-diazodicarboxylate In acetonitrile at 0℃; for 0.333333h; Mitsunobu reaction; | 78% |
With tetramethylphenylguanidine; diphenyl phosphoryl azide In acetonitrile at -40 - 20℃; | 75% |
phthalic anhydride
(R)-2-amino-3-phenylpropanol
(+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
at 140℃; | 96% |
With triethylamine In toluene for 3h; Condensation; Heating; | 93% |
at 200℃; for 3h; | 91% |
at 140 - 150℃; for 6h; | 82% |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Cooling with ice; | 96% |
(R)-2-amino-3-phenylpropanol
4,6-dichloro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine
(R)-β-<(1-phenyl-6-chloro-1H-pyrazolo<3,4-d>pyrimidin-4-yl)amino>benzenepropanol
Conditions | Yield |
---|---|
In ethanol for 48h; Ambient temperature; | 95% |
In ethanol | 95% |
(R)-2-amino-3-phenylpropanol
benzoyl chloride
N-benzoyl-D-phenylalaninol
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; | 95% |
With potassium carbonate In methanol at 20℃; | 95% |
With potassium carbonate In methanol at 20℃; | 95% |
With potassium carbonate In methanol at 20℃; Acylation; | |
With potassium carbonate In methanol at 20℃; |
4-Chloro-2-phenyl-7-propyl-2H-pyrazolo[3,4-d]pyrimidin-6(7H)-one
(R)-2-amino-3-phenylpropanol
(R)-4-(1-hydroxy-3-phenylprop-2-ylamino)-2-phenyl-7-propyl-2H-pyrazolo[3,4-d]pyrimidin-6(7H)-one
Conditions | Yield |
---|---|
In isopropyl alcohol Heating / reflux; | 95% |
(2-oxocyclopent)acetic acid
(R)-2-amino-3-phenylpropanol
(3R,5aR,8aS)-3-benzyl-hexahydro-1-oxa-3a-aza-cyclopenta[c]pentalen-4-one
Conditions | Yield |
---|---|
at 110℃; under 11251.1 Torr; Meyer synthesis; Microwave irradiation; optical yield given as %de; | 95% |
In water at 100℃; for 16h; | 80% |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With triethylamine In ethanol at 60℃; for 72h; | 94.1% |
(R)-2-amino-3-phenylpropanol
Boc-Phe-ONSu
tert-butyl ((2S)-1-(((2R)-1-hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran Ambient temperature; | 94% |
Conditions | Yield |
---|---|
In various solvent(s) at 80 - 85℃; for 2h; | 94% |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
In methanol at 20℃; for 3h; Inert atmosphere; optical yield given as %de; | 94% |
(R)-2-amino-3-phenylpropanol
tert-butyl N-{2-[4-(isothiocyanatomethyl)benzamido]phenyl}carbamate
tert-butyl N-(2-{4-[({[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamothioyl}amino)methyl]benzamido}phenyl)carbamate
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 16h; | 94% |
In tetrahydrofuran at 20℃; for 16h; |
(R)-2-amino-3-phenylpropanol
(R)-2-(2,3-bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride
Conditions | Yield |
---|---|
Stage #1: (R)-2-amino-3-phenylpropanol; 1-chloro-2,3-bis(dicyclohexylamino)cyclopropenium chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; for 12h; Stage #2: With hydrogenchloride In dichloromethane | 93% |
Conditions | Yield |
---|---|
Stage #1: thiophene-2-carbaldehyde; (R)-2-amino-3-phenylpropanol In methanol at 20℃; Stage #2: With sodium tetrahydroborate In ethanol at 0℃; Further stages.; | 92% |
Conditions | Yield |
---|---|
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 0.25h; Reduction; | 99% |
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; Reflux; | 99% |
With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran at 20℃; | 98% |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With sulfuric acid In water at 120℃; | 98% |
With sulfuric acid at 100℃; for 48h; Darkness; | 143.7 mg |
A
(R)-2-amino-3-phenylpropanol
B
(R)-3-phenylpropane-1,2-diamine
Conditions | Yield |
---|---|
With hydrogenchloride; methanol; water; hydrogen; 5% palladium over charcoal at 35℃; under 6750.68 - 22502.3 Torr; for 43h; | A 91% B 6% |
(R)-4-(phenylmethyl)-2-oxazolidinone
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With ammonium bromide; 3-azapentane-1,5-diamine at 90℃; for 5h; Microwave irradiation; | 84% |
9H-fluoren-9-ylmethyl (R)-<1-(hydroxymethyl)-2-phenylethyl>carbamate
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With piperidine In dichloromethane for 1h; Ambient temperature; | 82% |
D-phenylalanine methyl ester
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 0 - 10℃; for 1h; Temperature; Solvent; | 81% |
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With ammonium formate; palladium on activated charcoal In methanol for 2h; Heating; | 80% |
(+)-(R)-2-(1-benzyl-2-hydroxyethyl)-1H-isoindole-1,3(2H)-dione
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With hydrazine hydrate In acetonitrile for 4h; Heating; | 73% |
rac-phenylalaninol
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
Stage #1: rac-phenylalaninol With O,O'-dibenzoyl-L-tartaric acid In acetone at 25℃; for 6h; Stage #2: With potassium hydroxide In dichloromethane | 52% |
(L)-phenylalanine ethyl ester hydrochloride
A
L-Phenylalaninol
B
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere; optical yield given as %ee; | A 27% B n/a |
D-phenylalanine ethyl ester
(R)-2-amino-3-phenylpropanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether |
Molecular Structure:
Molecular Formula: C9H13NO
Molecular Weight: 151.2056
IUPAC Name: 2-Amino-3-phenylpropan-1-ol
Synonyms of D(+)-Phenylalaninol (CAS NO.5267-64-1): EINECS 226-086-1 ; (R)-2-Amino-3-phenylpropanol
CAS NO: 5267-64-1
Product Categories: Pharmaceutical Intermediates ; chiral ; Phenylalanine [Phe, F] ; Amino Alcohols (Chiral) ; Chiral Building Blocks ; Synthetic Organic Chemistry ; Amino alcohols
Melting point: 93-95 °C
Index of Refraction: 1.561
Molar Refractivity: 45.46 cm3
Molar Volume: 140.3 cm3
Surface Tension: 46.6 dyne/cm
Density: 1.077 g/cm3
Flash Point: 137.5 °C
Enthalpy of Vaporization: 57.46 kJ/mol
Boiling Point: 303.8 °C at 760 mmHg
Vapour Pressure: 0.0004 mmHg at 25°C
D(+)-Phenylalaninol (CAS NO.5267-64-1) is the Dextrorotatory form of the amino acid, Phenylalanine. It is not absorbed into the body. It acts as an inhibiting agent to the enzymes which are responsible for the breakdown of endorphins.
Hazard Codes of D(+)-Phenylalaninol (CAS NO.5267-64-1): C,Xi
Risk Statements: 34
R34: Causes burns.
Safety Statements: 26-36/37/39-45-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S27: Take off immediately all contaminated clothing.
RIDADR: UN 3259 8/PG 3
WGK Germany: 3
F: 10-23
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