(R)-2-azido-2-phenylacetic acid
(R)-phenylglycine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In water; acetic acid under 760 Torr; for 3h; | 97% |
Conditions | Yield |
---|---|
With nitrilase AY487533 In aq. acetate buffer at 20℃; for 1h; pH=8; Enzymatic reaction; enantioselective reaction; | 96.5% |
(R)-phenylglycine
Conditions | Yield |
---|---|
With hydrogenchloride; water In water at 110℃; for 3h; optical yield given as %ee; | 94% |
Boc-D-Phg-OH
(R)-phenylglycine
Conditions | Yield |
---|---|
With trifluoroacetic acid for 0.333333h; | 89% |
With hydrogenchloride; Dowex 50*8 1.) THF, room temperature, 2 h.; Yield given. Multistep reaction; |
6-Aminopenicillanic Acid
(R)-phenylglycine amide
A
(R)-phenylglycine
B
ampicillin
Conditions | Yield |
---|---|
With A. faecalis; immobilised penicillin acylase (EC 3.5.1.11) In water; acetonitrile at 0℃; Product distribution; Kinetics; Further Variations:; Solvents; reusing run; Enzymatic reaction; | A n/a B 86% |
N-(2,4,6-trimethyl-benzenesulfonyl)-D-phenylglycine
(R)-phenylglycine
Conditions | Yield |
---|---|
With sodium naphthalenide In 1,2-dimethoxyethane at -40℃; for 0.5h; | 78% |
(R)-(furan-2-yl)(phenyl)methanamine
(R)-phenylglycine
Conditions | Yield |
---|---|
With ozone In methanol at -78℃; for 0.25h; | 78% |
N-acetyl-α-phenylglycine
(R)-phenylglycine
Conditions | Yield |
---|---|
With water at 30℃; for 26h; D-aminoacylase from Streptomyces tuirus IFO 13418; | 74% |
MANDELIC ACID
(R)-phenylglycine
Conditions | Yield |
---|---|
With D-glucose; ammonia; ammonium chloride In aq. phosphate buffer at 30℃; for 24h; pH=8; Catalytic behavior; Reagent/catalyst; Microbiological reaction; Green chemistry; Enzymatic reaction; enantioselective reaction; | 71% |
[(1R)-2-(benzyloxy)-2-oxo-1-phenylethyl]ammonium 4-methyl-1-benzensulfonate
(R)-phenylglycine
Conditions | Yield |
---|---|
With hydrogenchloride Heating; | 69% |
styrene
(R)-phenylglycine
Conditions | Yield |
---|---|
With D-glucose; oleic acid ethyl ester; ammonia; oxygen; ammonium chloride In aq. phosphate buffer at 30℃; for 24h; pH=8; Catalytic behavior; Reagent/catalyst; Microbiological reaction; Green chemistry; Enzymatic reaction; enantioselective reaction; | 62% |
Multi-step reaction with 6 steps 1: styrene monooxygenase; NADPH; oxygen / Enzymatic reaction 2: epoxide hydrolase; water / Enzymatic reaction 3: alcohol dehydrogenase / Enzymatic reaction 4: aldehyde dehydrogenase; NAD / Enzymatic reaction 5: recombinant Escherichia coli expressing SMDH / aq. phosphate buffer / 0.5 h / 30 °C / pH 8 / Microbiological reaction; Enzymatic reaction 6: recombinant Escherichia coli DL39 (DE3) expressing DpgAT; L-glutamate / aq. phosphate buffer / 5 h / 30 °C / pH 8 / Microbiological reaction; Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
With D-glucose; oleic acid ethyl ester; ammonia; ammonium chloride In aq. phosphate buffer at 30℃; for 24h; pH=8; Catalytic behavior; Reagent/catalyst; Microbiological reaction; Green chemistry; Enzymatic reaction; enantioselective reaction; | 53% |
Multi-step reaction with 3 steps 1: phenylalanine ammonia lyase / Enzymatic reaction 2: pheylacrylic acid decarboxylase / Enzymatic reaction 3: ammonia; ammonium chloride; D-glucose; oleic acid ethyl ester; oxygen / aq. phosphate buffer / 24 h / 30 °C / pH 8 / Microbiological reaction; Green chemistry; Enzymatic reaction View Scheme | |
Multi-step reaction with 8 steps 1: phenylalanine ammonia lyase / Enzymatic reaction 2: pheylacrylic acid decarboxylase / Enzymatic reaction 3: styrene monooxygenase; NADPH; oxygen / Enzymatic reaction 4: epoxide hydrolase; water / Enzymatic reaction 5: alcohol dehydrogenase / Enzymatic reaction 6: aldehyde dehydrogenase; NAD / Enzymatic reaction 7: recombinant Escherichia coli expressing SMDH / aq. phosphate buffer / 0.5 h / 30 °C / pH 8 / Microbiological reaction; Enzymatic reaction 8: recombinant Escherichia coli DL39 (DE3) expressing DpgAT; L-glutamate / aq. phosphate buffer / 5 h / 30 °C / pH 8 / Microbiological reaction; Enzymatic reaction View Scheme |
(R)-Phenylglycine methyl ester
(R)-phenylglycine
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Hydrolysis; | 35% |
Chloro-phenyl-acetic acid
(R)-phenylglycine
Conditions | Yield |
---|---|
With ammonia; benzonitrile | |
With ammonia | |
With ammonia; acetonitrile | |
With n-heptan1ol; ammonia |
(R)-phenylglycine amide
(R)-phenylglycine
Conditions | Yield |
---|---|
With hydrogen bromide | |
Multi-step reaction with 2 steps 1: 42 percent / Alcaligenes faecalis penicillin acylase; potassium hydroxide / H2O / 0.28 h / 25 °C / pH 10 2: Alkaligenes faecalis penicillin acylase / 25 °C / pH 7.5 View Scheme |
N-[(2S)-(benzoylamino)(phenyl)]ethanoic acid
(R)-phenylglycine
Conditions | Yield |
---|---|
With hydrogenchloride |
(R)-2-bromo-2-phenylacetic acid
(R)-phenylglycine
Conditions | Yield |
---|---|
With ammonia; acetonitrile |
(R)-(2-chloro-acetylamino)-phenyl-acetic acid
(R)-phenylglycine
Conditions | Yield |
---|---|
With hydrogenchloride |
(R)-D-mandeloylamino-phenyl-acetic acid
(R)-phenylglycine
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With (1S)-10-camphorsulfonic acid |
Conditions | Yield |
---|---|
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; pH 8.0; enzymatic reaction; | |
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; |
(Z)-2-(hydroxyimino)-2-phenylacetic acid
A
(S)-2-phenylglycine
B
(R)-phenylglycine
Conditions | Yield |
---|---|
With buffered acetic acid; strychnidin-10-one; mercury Product distribution; var. strychnine concentrations, other cathodic potentials (E): -1.05, -1.15, -1.30 V (SCE); object of study: optical yield; |
N-carbamoyl-D,L-phenylglycine
(R)-phenylglycine
Conditions | Yield |
---|---|
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; | |
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; pH 7.5; enzymatic reaction; |
(R)-phenylglycine
Conditions | Yield |
---|---|
With lithium hydroxide; ion exchange 1.) THF; Yield given. Multistep reaction; |
Phenylglycine p-nitrophenyl ester
A
(S)-2-phenylglycine
B
(R)-phenylglycine
Conditions | Yield |
---|---|
With (R)-<methyl>pyridine; copper(II) ion In various solvent(s) at 25℃; Rate constant; enantioselectivity of cleavage; other chiral ligands; |
chloroform
benzaldehyde
A
(S)-2-phenylglycine
B
(R)-phenylglycine
Conditions | Yield |
---|---|
With potassium hydroxide; ammonia; (+)-(1S,2R)-N-hexadecyl-N-methylephedrinium bromide; lithium chloride In ethanol Product distribution; 5 deg C, 4 h, RT, overnight; asymmetric induction; |
(R)-2-Amino-N-tert-butyl-2-phenyl-acetamide; hydrochloride
(R)-phenylglycine
Conditions | Yield |
---|---|
With hydrogenchloride In water at 80℃; Yield given; |
(2S)-2-phenyl-2-(tosylamino)acetic acid
A
(S)-2-phenylglycine
B
(R)-phenylglycine
Conditions | Yield |
---|---|
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; samarium diiodide In tetrahydrofuran for 9h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(+/-)-α-phenylglycine hydrochloride
(R)-phenylglycine
Conditions | Yield |
---|---|
With thionyl chloride for 2h; Heating; | 100% |
With thionyl chloride In methanol at 20℃; Cooling with ice; | 99% |
With thionyl chloride at 0 - 75℃; for 2h; | 98.9% |
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; 5% Pd(II)/C(eggshell) In methanol; water under 1810.07 - 2068.65 Torr; for 4h; | 100% |
With hydrogenchloride; hydrogen; 5%-palladium/activated carbon In methanol; water under 1810.07 - 2068.65 Torr; for 4h; | 100% |
With hydrogenchloride; hydrogen; 5%-palladium/activated carbon In methanol; water under 1810.07 - 2068.65 Torr; for 4h; | 100% |
Conditions | Yield |
---|---|
With sodium hydroxide In tert-butyl alcohol at 20℃; for 1h; Inert atmosphere; | 100% |
With potassium hydrogencarbonate In tetrahydrofuran; water for 18h; | 99% |
With sodium hydroxide | 96% |
formic acid
(R)-phenylglycine
(2R)-2-(N-formyl)amino-2-phenylacetic acid
Conditions | Yield |
---|---|
With acetic anhydride at 20℃; for 1h; | 100% |
(R)-phenylglycine
Allyl chloroformate
(2R)-{[(allyloxy)carbonyl]amino}(phenyl)acetic acid
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran at 0℃; for 0.25h; | 99% |
(R)-phenylglycine
4-diphenylsulfonyl chloride
N-(biphenyl-4-sulfonyl)-D-phenylglycine
Conditions | Yield |
---|---|
With sodium hydroxide In diethyl ether at 20℃; for 16h; | 99% |
benzothiazole-2-sulfonyl chloride
(R)-phenylglycine
(R)-(Benzothiazole-2-sulfonylamino)-phenyl-acetic acid
Conditions | Yield |
---|---|
With sodium hydroxide at 10℃; for 10h; | 97% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 50℃; for 6.5h; Cooling with ice; | 96.8% |
Stage #1: (R)-phenylglycine With sulfuric acid; nitric acid In water at 0℃; for 3h; Stage #2: With ammonia In water | 62% |
(R)-phenylglycine
(R)-2-bromo-2-phenylacetic acid
Conditions | Yield |
---|---|
With hydrogen bromide; sodium nitrite at 0℃; for 2h; | 96% |
Stage #1: (R)-phenylglycine With sulfuric acid; potassium bromide In water Stage #2: With sodium nitrite In water at 0 - 20℃; for 2.5h; | |
With sulfuric acid; potassium bromide; sodium nitrite In water |
phthalic anhydride
(R)-phenylglycine
(R)-2-(1,3-dioxoisoindolin-2-yl)-2-phenylacetic acid
Conditions | Yield |
---|---|
With triethylamine In toluene at 130℃; for 3h; Dean-Stark; | 96% |
With acetic acid at 120℃; for 12h; Reflux; |
(R)-phenylglycine
(R)-2-amino-2-cyclohexyl acetic acid
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen In water; isopropyl alcohol at 50 - 60℃; for 6 - 8h; | 95.8% |
With hydrogen; platinum(IV) oxide In acetic acid Ambient temperature; | 91% |
With hydrogenchloride; hydrogen; rhodium under 38000 Torr; for 240h; | 79% |
With hydrogenchloride; platinum at 70℃; Hydrogenation; | |
With hydrogenchloride; hydrogen; platinum(IV) oxide In ethanol |
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 20℃; Reflux; Inert atmosphere; | 95% |
With hydrogenchloride | |
With thionyl chloride at 20℃; |
(R)-phenylglycine
toluene-4-sulfonic acid
L-(+)-α-Phenylglycine p-toluenesulfonate salt
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane; dichloromethane at 40℃; for 2h; | 95% |
(R)-phenylglycine
toluene-4-sulfonic acid
D-(-)-α-Phenylglycine p-toluenosulfonate salt
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane; dichloromethane at 40℃; for 2h; | 95% |
(R)-phenylglycine
Hexafluoroacetone
(R)-4-Phenyl-2,2-bis-trifluoromethyl-oxazolidin-5-one
Conditions | Yield |
---|---|
95% |
(R)-phenylglycine
toluene-4-sulfonic acid
benzyl alcohol
[(1R)-2-(benzyloxy)-2-oxo-1-phenylethyl]ammonium 4-methyl-1-benzensulfonate
Conditions | Yield |
---|---|
In cyclohexane; water for 4h; Dean-Stark; Reflux; | 95% |
With water In toluene Heating; | 89% |
(R)-phenylglycine
phenyl isothiocyanate
(R)-phenyl-(3'-phenyl-thioureido)acetic acid
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 24h; | 95% |
Stage #1: (R)-phenylglycine With sodium hydroxide In tetrahydrofuran; water for 0.25h; Stage #2: phenyl isothiocyanate In tetrahydrofuran; water at 20℃; |
(R)-phenylglycine
(R)-Phenylglycinol
Conditions | Yield |
---|---|
Stage #1: (R)-phenylglycine With sodium tetrahydroborate; iodine In tetrahydrofuran at 64℃; for 18h; Stage #2: With methanol In tetrahydrofuran at 20℃; | 94% |
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 0 - 20℃; for 49h; | 93% |
With lithium aluminium tetrahydride In tetrahydrofuran for 20h; Heating; | 92% |
(R)-phenylglycine
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
Boc-D-Phg-OH
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water for 18h; | 94% |
(R)-phenylglycine
3,5-bistrifluoromethylphenylisothiocyanate
(R)-[3'-(3,5-bis-trifluoromethyl)phenyl-thioureido]-phenyl acetic acid
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 24h; | 94% |
Stage #1: 3,5-bistrifluoromethylphenylisothiocyanate With sodium hydroxide In tetrahydrofuran; water for 0.25h; Stage #2: (R)-phenylglycine In tetrahydrofuran; water at 20℃; |
Conditions | Yield |
---|---|
With molecular sieve In methanol; ethanol under N2; aq. NaOH added to amino acid, soln. stirred (room temp., 5 min), soln. concd. (vac.), residue dried at 60°C (vac., 16 h), molecular sieves (4 Angstroem), ferrocenecarboxaldehyde and EtOH/MeOH added, mixt. stirred (room temp., 16 h); molecular sieves filtered off, filtrate concd. under vac., residue suspd. in pentane, solid filtered off, washed with pentane, dried under vac.; | 94% |
(R)-phenylglycine
acetic anhydride
(R)-(-)-N-acetylphenylglycine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0℃; for 6h; pH=11-12; Temperature; | 93.4% |
Stage #1: (R)-phenylglycine With sodium hydroxide In water for 0.0333333h; Stage #2: acetic anhydride In water at 20℃; for 0.25h; Stage #3: With hydrogenchloride In water pH=1; | 80% |
With sodium hydroxide In water at 0 - 5℃; pH=5; | 32% |
With sodium hydroxide In water at 0 - 5℃; for 0.5h; | |
In water at 70℃; for 0.5h; |
(R)-phenylglycine
(1S)-(-)-camphanic chloride
Conditions | Yield |
---|---|
In tetrahydrofuran for 288h; | 93% |
Conditions | Yield |
---|---|
With pyridine; sodium hydroxide In acetone at 4℃; for 2h; | 93% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water at 80℃; for 0.00972222h; Substitution; microwave irradiation; | 93% |
ethyl trifluoroacetate,
(R)-phenylglycine
(-)-(R)-N-trifluoroacetylphenylglycine
Conditions | Yield |
---|---|
Stage #1: (R)-phenylglycine With N,N,N',N'-tetramethylguanidine In methanol for 0.0833333h; Stage #2: ethyl trifluoroacetate, In methanol at 20℃; for 30h; | 93% |
With 1,1,3,3-tetramethylguanidine In methanol at 20℃; for 24h; | 93% |
Conditions | Yield |
---|---|
With sodium hydroxide for 0.166667h; | 92% |
With sodium hydroxide | 88% |
With sodium hydroxide at 0℃; for 1h; | 82% |
IUPAC Name: (2R)-2-azaniumyl-2-phenylacetate
Empirical Formula: C8H9NO2
Molecular Weight: 151.1626g/mol
EINECS: 212-876-3
Structure of D-2-Phenylglycine (CAS NO.875-74-1):
Index of Refraction: 1.589
Molar Refractivity: 40.9 cm3
Molar Volume: 121.3 cm3
Polarizability: 16.21×10-24cm3
Surface Tension: 57 dyne/cm
Density: 1.246 g/cm3
Flash Point: 128.4 °C
Enthalpy of Vaporization: 55.75 kJ/mol
Melting Point: 302 °C (dec.)(lit.)
Boiling Point: 288.7 °C at 760 mmHg
Vapour Pressure: 0.00107 mmHg at 25°C
Water Solubility: 0.3g/100mL
Product Categories: GLYCINESCAFFOLD;Pharmaceutical Intermediates;Amino ACIDS SERIES;Phenylglycine [Phg];Unusual Amino Acids;Amino Acids
Canonical SMILES: C1=CC=C(C=C1)C(C(=O)[O-])[NH3+]
Isomeric SMILES: C1=CC=C(C=C1)[C@H](C(=O)[O-])[NH3+]
InChI: InChI=1S/C8H9NO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,9H2,(H,10,11)/t7-/m1/s1
InChIKey: ZGUNAGUHMKGQNY-SSDOTTSWSA-N
Hazard Codes: T
Risk Statements: 23/24/25-36/37/38
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
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.
WGK Germany: 3
HS Code: 29224995
D-2-Phenylglycine , its cas register number is 875-74-1. It also can be called Benzeneacetic acid, alpha-amino-, (alphaR)- ;
D-(-)-alpha-Phenylglycine . D-2-Phenylglycine (CAS NO.875-74-1) is a white crystalline powder.
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