N-<(2R,4E)-2-Methyl-4-hexenoyl>-S-phenylglycinol
A
(2S)-2-phenylglycinol
B
(2R,4E)-2-Methyl-4-hexenoic acid
Conditions | Yield |
---|---|
With sulfuric acid In 1,4-dioxane at 70 - 80℃; for 3h; | A 92% B 99% |
(S)-2-phenylglycine
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran Heating; | 97% |
With lithium aluminium tetrahydride In tetrahydrofuran Heating; | 97% |
With lithium aluminium tetrahydride In tetrahydrofuran Heating; | 95% |
tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
In acetonitrile at 300℃; under 75007.5 Torr; | 93% |
(S)-Phenylglycine methyl ester
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Reflux; | 88% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1.5h; Reflux; | 88% |
Stage #1: (S)-Phenylglycine methyl ester With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 0.25h; Stage #2: With methanol In tetrahydrofuran at 65℃; stereospecific reaction; | 73% |
With sodium tetrahydroborate In methanol at 20℃; for 1h; | |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1h; Cooling with ice; Inert atmosphere; |
(S)-4-phenyl-2-oxazolidinone
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With 3-azapentane-1,5-diamine at 140℃; for 18h; | 85% |
L-2-phenylglycine methyl ester hydrochloride
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol 1) RT, 9h, b) 5.5h, reflux, c) RT, 8h; | 83% |
With sodium tetrahydroborate In ethanol; water for 5.5h; Heating; | |
Stage #1: L-2-phenylglycine methyl ester hydrochloride With triethylamine In methanol; diethyl ether at -10℃; for 1h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; | 4.4 g |
N-(2-methoxymethoxy-1-phenyl-ethyl)-acetamide
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
In methanol Hydrolysis; Acid hydrolysis; | 81% |
benzyl (S)-(2-hydroxy-1-phenylethyl)carbamate
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With hydrogen; palladium dihydroxide In methanol for 0.25h; | 80% |
Phenylglycinol
A
(R)-Phenylglycinol
B
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With hydrogenchloride; (S)-(+)-3,3′-bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate In dichloromethane; water at 21.84℃; pH=2.32; Centrifugal contactor separators; Resolution of racemate; optical yield given as %ee; | A n/a B 36% |
With chiral stationary phase including isopropyl-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 20℃; Purification / work up; | |
With 3,3'-bis[3,5-bis(trifluoromethyl)phenyl]-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In tetrachloromethane at 6℃; pH=3; aq. buffer; enantioselective reaction; |
(S)-2-phenylglycine
B
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Stage #1: (S)-2-phenylglycine With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran; diethyl ether at 0 - 20℃; for 20h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 20℃; for 2h; | A 27% B 33% |
(S)-phenylglycine ethyl ester
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride |
(S)-2-azido-2-phenylethanol
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran Heating; Yield given; |
(1S,2S,5S)-3-[(E)-(S)-2-Hydroxy-1-phenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With hydroxylamine acetate In ethanol for 20h; Ambient temperature; Yield given; |
Phenylglycinol
(2S)-2-phenylglycinol
tert-butyl 2-hydroxy-1-phenylethylcarbamate
A
(R)-Phenylglycinol
B
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(1S,1'S)-N-2'-hydroxy-1'-phenylethyl-1-phenylethylamine
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With hydrogen S, Ram, L. D. Spicer Synth. Commun. 1987, 17, 415.; |
(R)-Styrene oxide
A
(2S)-2-phenylglycinol
B
(R)-2-Amino-1-phenylethanol
Conditions | Yield |
---|---|
With ammonium hydroxide In water at 130℃; under 9000.72 Torr; microwave irradiation; | A 20 % Chromat. B 80 % Chromat. |
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With hydrogen; nickel In methanol at 25℃; under 25857.4 Torr; for 28h; | 0.136 g |
C18H26N2O5
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaBH4 / methanol 2: TFA / CH2Cl2 / 3 h / 20 °C 3: 0.136 g / H2 / Raney-Ni / methanol / 28 h / 25 °C / 25857.4 Torr View Scheme |
C18H28N2O5
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 3 h / 20 °C 2: 0.136 g / H2 / Raney-Ni / methanol / 28 h / 25 °C / 25857.4 Torr View Scheme |
phenylacetaldehyde
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: D-proline / CH2Cl2 / 3 h / 20 °C 2: NaBH4 / methanol 3: TFA / CH2Cl2 / 3 h / 20 °C 4: 0.136 g / H2 / Raney-Ni / methanol / 28 h / 25 °C / 25857.4 Torr View Scheme |
ethyl 2-(hydroxyimino)-2-phenylacetate
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 85 percent / NaBH4; I2 / tetrahydrofuran / 4 h / Heating 2.1: dibenzoyl-L-tartaric acid / acetone / 6 h / 25 °C 2.2: aq. KOH / CH2Cl2 View Scheme |
(4-Methoxy-phenyl)-[(S)-1-phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-amine
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 80 percent / CAN / H2O; acetonitrile / 0.5 h / 0 °C 2: 80 percent / K2CO3 / dioxane; H2O / 0.17 h / Ambient temperature 3: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min 4: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 70 percent / DOWEX 50W X8-400 / benzene / Heating 2: LDA / tetrahydrofuran; hexane / -70 °C / 1.) 15 min, 2.) 30 min 3: 80 percent / CAN / H2O; acetonitrile / 0.5 h / 0 °C 4: 80 percent / K2CO3 / dioxane; H2O / 0.17 h / Ambient temperature 5: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min 6: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h View Scheme | |
Multi-step reaction with 3 steps 1: 4 Angstroem mol. sieves / CH2Cl2 2: TiCl4 / 15 °C / Irradiation 3: H2 / S, Ram, L. D. Spicer Synth. Commun. 1987, 17, 415. View Scheme |
4-methoxy-N-[(E)-phenylmethylidene]aniline
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: LDA / tetrahydrofuran; hexane / -70 °C / 1.) 15 min, 2.) 30 min 2: 80 percent / CAN / H2O; acetonitrile / 0.5 h / 0 °C 3: 80 percent / K2CO3 / dioxane; H2O / 0.17 h / Ambient temperature 4: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min 5: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h View Scheme |
(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethylamine
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / K2CO3 / dioxane; H2O / 0.17 h / Ambient temperature 2: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min 3: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h View Scheme |
[(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) (CF3CO)2O, sym-collidine, 2.) K2CO3, NaBH4 / 1.) MeCN, 0 deg C, 5 min, 2.) H2O, 0 deg C to room temperature, 15 min 2: 80 percent / H2 / Pd(OH)2/C / methanol / 0.25 h View Scheme |
N-benzylidene-(S)-α-methylbenzylamine
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TiCl4 / 15 °C / Irradiation 2: H2 / S, Ram, L. D. Spicer Synth. Commun. 1987, 17, 415. View Scheme |
1-phenyl-2-hydroxyethanone
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: LiH / dimethylformamide 2: H2NOH*HCl; NaOAc / ethanol; H2O 3: Fe / dimethylformamide 4: 100 percent / H2 / {1,2-bis[(R,R)-2,5-dimethylphospholane]benzene}rhodium(I) / toluene / 20 °C / 7600 Torr 5: 81 percent / methanol / Acid hydrolysis View Scheme | |
With ω-transaminase from Arthrobacter; isopropylamine In tert-butyl methyl ether at 25℃; for 24h; Enzymatic reaction; enantioselective reaction; | n/a |
With (R)-1-phenyl-ethyl-amine; (R)-ω-transaminase from Mycobacterium vanbaalenii; NAD Enzymatic reaction; enantioselective reaction; |
2-methoxymethoxy-1-phenyl-ethanone
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: H2NOH*HCl; NaOAc / ethanol; H2O 2: Fe / dimethylformamide 3: 100 percent / H2 / {1,2-bis[(R,R)-2,5-dimethylphospholane]benzene}rhodium(I) / toluene / 20 °C / 7600 Torr 4: 81 percent / methanol / Acid hydrolysis View Scheme |
(2S)-2-phenylglycinol
tert-butyldimethylsilyl chloride
(S)-2-(tert-butyldimethylsilyloxy)-1-phenylethylamine
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 41h; Substitution; | 100% |
With dmap; triethylamine In dichloromethane at 20℃; for 12h; | 85% |
With dmap; triethylamine In dichloromethane at 20℃; | 85% |
(2S)-2-phenylglycinol
acetoacetic acid methyl ester
(Z)-3-((S)-2-Hydroxy-1-phenyl-ethylamino)-but-2-enoic acid methyl ester
Conditions | Yield |
---|---|
In methanol for 24h; Heating; | 100% |
formaldehyd
(2S)-2-phenylglycinol
(S)-2-(N,N-dimethylamino)-2-phenylethanol
Conditions | Yield |
---|---|
With HCOOH (98percent) In water for 18h; Heating; | 100% |
4-(4-chlorophenyl)-4-oxobutanoic acid
(2S)-2-phenylglycinol
(3S,7aS)-7a-(4-Chloro-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
Conditions | Yield |
---|---|
In toluene for 16h; Heating; | 100% |
(2S)-2-phenylglycinol
4-(2,4-dichlorophenyl)-4-oxobutanoic acid
(3S,7aS)-7a-(2,4-Dichloro-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
Conditions | Yield |
---|---|
In toluene for 16h; Heating; | 100% |
(2S)-2-phenylglycinol
4-(2,4-difluorophenyl)-4-oxobutanoic acid
(3S,7aS)-7a-(2,4-Difluoro-phenyl)-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
Conditions | Yield |
---|---|
In toluene for 16h; Heating; | 100% |
2-methyl-benzyl alcohol
(2S)-2-phenylglycinol
2-{(E)-((1S)-2-hydroxy-1-phenylethylimino)methyl}phenol
Conditions | Yield |
---|---|
With sodium sulfate In methanol for 12h; Heating; | 100% |
In ethanol at 20℃; |
(2S)-2-phenylglycinol
ethyl 5-formyl-3-methoxy-4-methyl-1H-pyrrole-2-carboxylate
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane | 100% |
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
In chloroform-d1 at 24℃; | 100% |
(2S)-2-phenylglycinol
ethyl (E,E)-4-oxo-2-styrylbut-2-enoate
Conditions | Yield |
---|---|
In chloroform-d1 at 24℃; | 100% |
(2S)-2-phenylglycinol
acrolein
(3S,9S)-3,9-diphenyloctahydro-5H,11H-bis[1,3]oxazolo[3,2-a:3',2'-e][1,5]diazocine
Conditions | Yield |
---|---|
In chloroform at 20℃; for 0.0833333h; | 100% |
In toluene at 20℃; for 15h; Molecular sieve; | 36% |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice; | 100% |
di-tert-butyl dicarbonate
(2S)-2-phenylglycinol
tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 3h; Acylation; | 99% |
In chloroform at 0 - 20℃; | 97% |
With triethylamine In tetrahydrofuran for 2h; | 96% |
(2S)-2-phenylglycinol
(+)-dimethyl-2,3-O-isopropylidene-D-tartrate
(4S,5S)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide]
Conditions | Yield |
---|---|
at 120℃; for 3h; | 99% |
(E)-3-phenylpropenal
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
In diethyl ether for 1.33333h; Ambient temperature; | 99% |
carbon disulfide
(2S)-2-phenylglycinol
(S)-4-phenyl-1,3-oxazolidine-2-thione
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium carbonate In ethanol at 50℃; | 99% |
Stage #1: carbon disulfide; (2S)-2-phenylglycinol With triethylamine In methanol at 20℃; for 0.5h; Stage #2: With dihydrogen peroxide In methanol | 95% |
With dihydrogen peroxide; potassium carbonate In ethanol at 50℃; for 0.0833333h; | 80% |
2-methoxy-6-methyl-benzaldehyde
(2S)-2-phenylglycinol
(+)-(βS)-β-{[(1E)-(2-methoxy-6-methylphenyl)methylene]amino}benzeneethanol
Conditions | Yield |
---|---|
With 4A MS In ethanol at 20℃; for 26h; | 99% |
(R)-1,1'-spirobiindane-7,7'-dicaboxylic acid
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at -5 - 20℃; | 99% |
trans-2-phenylvinylboronic acid
(2S)-2-phenylglycinol
glyoxalic acid monohydrate
D-homophenylalanine
Conditions | Yield |
---|---|
In dichloromethane | 99% |
Conditions | Yield |
---|---|
In toluene at 20℃; for 4h; Molecular sieve; | 99% |
(2S)-2-phenylglycinol
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
(2-hydroxy-1-phenylethyl)carbamic acid 9H-fluoren-9-ylmethyl ester
Conditions | Yield |
---|---|
In 1,4-dioxane; water at 20℃; for 16h; | 99% |
(2S)-2-phenylglycinol
formic acid ethyl ester
Conditions | Yield |
---|---|
Reflux; | 99% |
3,3-dimethylglutaric anhydride
(2S)-2-phenylglycinol
3-(((S)-2-hydroxy-1-phenylethyl-carbamoyl)methyl)-3-methylbutanoic acid
Conditions | Yield |
---|---|
In dichloromethane; toluene at 20 - 60℃; for 5.5h; | 99% |
4-Bromobenzoic acid
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-ol; 1,2-dichloro-ethane In N,N-dimethyl-formamide at 25℃; for 20h; Solvent; chemoselective reaction; | 99% |
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In tetrahydrofuran at 20℃; for 20h; | 60% |
2-amino-3-pyridinecarbonitrile
(2S)-2-phenylglycinol
Conditions | Yield |
---|---|
With zinc(II) chloride In chlorobenzene at 60℃; for 96h; Inert atmosphere; | 99% |
Molecular Structure of (S)-(+)-2-Phenylglycinol (CAS NO.20989-17-7):
IUPAC Name: (2S)-2-amino-2-phenylethanol
Empirical Formula: C8H11NO
Molecular Weight: 137.179
H bond acceptors: 2
H bond donors: 3
Freely Rotating Bonds: 4
Polar Surface Area: 12.47 Å2
Index of Refraction: 1.572
Molar Refractivity: 40.87 cm3
Molar Volume: 124.1 cm3
Surface Tension: 48.8 dyne/cm
Density: 1.104 g/cm3
Flash Point: 125.3 °C
Enthalpy of Vaporization: 52.69 kJ/mol
Boiling Point: 261 °C at 760 mmHg
Vapour Pressure: 0.00601 mmHg at 25°C
Melting point: 76-79 °C
Storage temp: Store at 0-5°C
Sensitive: Air Sensitive
InChI
InChI=1/C8H11NO/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/t8-/m1/s1
Smiles
c1(ccccc1)[C@@H](CO)N
Handling: Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage: Store in a cool, dry place. Store in a tightly closed container. Corrosives area. Store under nitrogen.
Product Categories: Pharmaceutical Intermediates; Alcohols and Derivatives; chiral; Chiral Reagent; Phenylglycine [Phg]; Amino Acids 13C, 2H, 15N; Amino Alcohols (Chiral); Asymmetric Synthesis; Chiral Building Blocks; Synthetic Organic Chemistry; Amino alcohols; Amino Acids & Derivatives
Risk Statements: 34-36/37/38-23/24/25
R34:Causes burns.
R36/37/38:Irritating to eyes, respiratory system and skin.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-24/25-45-36/37/39-26
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
Hazard Codes: C,T
WGK Germany: 3
F: 2-10
(S)-(+)-2-Phenylglycinol , with CAS number of 20989-17-7, can be called (R)/(S)-Phenylglycinol ; 2-Amino-2-pheynlethanol ; Benzeneethanol, beta-amino-, (S)- ; (2S)-2-amino-2-phenyl-ethanol ; (S)-(+)-2-Amino-2-phenylethanol ; (S)-(+)-2-Pheny ; S-(+)-2-Phenylglycinol (>=99%) ; (S)-(-)-2-Phenylalanine ; L-(+)-2-Phenylglycinol ; (S)-(+)-2-Amino-2-Phenylethanol; (S)-(+)-2- . It is a white to light yellow crystal powde.
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