(3R,6S)-4-N-((S)-1-phenethyl)-3-benzyl-6-methyl-1,4-morpholin-2,5-dione
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With hydrogen iodide for 1h; Heating; | 100% |
N-Cbz-O-benzyl phenylalanine
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With 10% Pd/C; cyclohexa-1,4-diene In methanol at 100℃; for 0.0833333h; Microwave irradiation; | 100% |
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 40℃; for 6h; | 100% |
With hydrogenchloride In methanol; water at 40℃; for 6h; | 96% |
phenylalanine amide hydrochloride
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate monohydrate In aq. buffer at 40℃; for 6h; pH=8.0; Enzymatic reaction; | 99% |
(R)-2-azido-3-phenylpropanoic acid
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In water; acetic acid under 7757.2 Torr; for 1h; | 97% |
t-butyl (RS)-phenylalaninate
D-(R)-phenylalanine
Conditions | Yield |
---|---|
95% |
(3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(phenylmethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With hydrogen; palladium dichloride In tetrahydrofuran; ethanol under 2585.7 Torr; for 20h; | 93% |
Conditions | Yield |
---|---|
With hydrogen; platinum(IV) oxide | 89% |
(2R,2'R)-N-(2'-amino-3'-phenylpropanoyl)bornane-10,2-sultam
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran at 20℃; | 87% |
With lithium hydroxide; ion exchange 1.) THF; Yield given. Multistep reaction; | |
With lithium hydroxide; Amberlite IR-120 1) THF, room temperature, 2) H2O, room temperature, 15 h; Yield given. Multistep reaction; |
C32H38N2O3
D-(R)-phenylalanine
Conditions | Yield |
---|---|
Stage #1: C32H38N2O3 With hydrogenchloride; hydrogen; palladium(II) hydroxide/carbon In tetrahydrofuran; water at 50℃; for 48h; Stage #2: With hydrogenchloride; water for 3.5h; Heating / reflux; Stage #3: With sodium hydroxide; water pH=2.5; Product distribution / selectivity; | 87% |
(R)-2-(benzhydrylamino)-3-phenylpropanenitrile
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride; water for 3h; Reflux; optical yield given as %ee; | 87% |
methyl 2-amino-3-phenylpropanoate hydrochloride
A
L-phenylalanine
B
D-(R)-phenylalanine
C
D-phenylalanine methyl ester
Conditions | Yield |
---|---|
at 30℃; for 0.333333h; enzyme alcalase from Bacillus licheniforms; pH 8.0; Yields of byproduct given; | A n/a B n/a C 85% |
at 30℃; for 0.333333h; enzyme alcalase from Bacillus licheniforms, pH 8.0; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
(R)-N-benzyl-phenylalanine
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In acetic acid for 24h; | 85% |
D-(R)-phenylalanine
Conditions | Yield |
---|---|
Stage #1: C15H15N3*C16H13Cl2NO3 With hydrogenchloride In acetonitrile at 20℃; for 1h; Stage #2: With triethylamine In ethanol; dichloromethane at 20℃; for 1h; | 85% |
N-triphenylmethylsulfenyl-D-phenylalanine
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride In toluene at 115℃; for 0.0833333h; | 82% |
(1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one
D-(R)-phenylalanine
Conditions | Yield |
---|---|
Stage #1: (1R,2S,5R,8S)-5-benzyl-1,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one With hydrogenchloride at 87℃; for 2h; Stage #2: With methyloxirane In ethanol at 20℃; for 0.5h; Further stages.; | 82% |
(S,S)-pseudoephedrine D-phenylalaninamide
A
pseudoephedrine
B
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With water for 18h; Heating; | A n/a B 77% |
(S,S)-pseudoephedrine D-phenylalaninamide
D-(R)-phenylalanine
Conditions | Yield |
---|---|
In water for 18h; Heating; other reagent; | 77% |
With water Heating; | 70% |
Conditions | Yield |
---|---|
With D-glucose; nicotinamide adenine dinucleotide phosphate; ammonium chloride In aq. buffer at 20℃; for 24h; pH=9; Microbiological reaction; enantioselective reaction; | 76% |
In water at 140℃; Rate constant; pH 8.0; | |
Stage #1: L-phenylalanine With (S)-2-hydroxy-2'-(3-(N-phenylcarbamoylamino)benzyl)-1,1'-binaphthyl-3-carboxaldehyde; triethylamine In dimethylsulfoxide-d6 at 40℃; for 24h; Stage #2: With hydrogenchloride; water In chloroform enantioselective reaction; |
Conditions | Yield |
---|---|
With D-glucose; nicotinamide adenine dinucleotide phosphate; ammonium chloride In methanol at 20℃; for 24h; pH=9; Solvent; Microbiological reaction; enantioselective reaction; | 72% |
With meso-2,6-D-diaminopimelic acid dehydrogenase mutant BC621; ammonium chloride; NADPH In various solvent(s) for 24h; | |
With D-glucose; pyridoxal 5'-phosphate; D-amino acid aminotransferase from Bacillus sp mutant T242G In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 12h; pH=8; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | n/a |
D-(R)-phenylalanine
Conditions | Yield |
---|---|
Stage #1: C34H33N3NiO3 With hydrogenchloride In methanol at 70℃; Stage #2: In water | 71% |
(R)-(N-allyloxycarbonyl)phenylalanine
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With diethylamine; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 20℃; for 0.166667h; | 70% |
Conditions | Yield |
---|---|
With D-Alanine; meso-diaminopimelate dehydrogenase; pyridoxal 5'-phosphate; alcohol dehydrogenases from Bacillus stearothermophilus; alcohol dehydrogenases from Thermoanaerobacter brockii; NADH In isopropyl alcohol at 35℃; for 9h; pH=8; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | 43.4% |
(-)-1-<(1-cyano-2-phenylethyl)amino>-2R-methyl-5R-(1-methylethenyl)cyclohexane-1R,3R-dicarbonitrile
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride at 110℃; for 12h; | 41% |
Conditions | Yield |
---|---|
With sodium hydroxide; oxygen; 2-amino-2-hydroxymethyl-1,3-propanediol In water at 30℃; for 5h; pH=7.3; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | 38% |
durch partielle Vergaerung mit lebender Hefe bei Gegenwart von Zucker; |
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With hydrogen; palladium on carbon In water at 50℃; for 25h; Product distribution / selectivity; | 31% |
(R)-N-acetylphenylalanin
D-(R)-phenylalanine
Conditions | Yield |
---|---|
In water at 37℃; for 0.166667h; Rate constant; D-aminocyclase from Alcaligenes denitrificans DA181, pH 7.8, bovine serum albumin; | |
With hydrogenchloride | |
With hydrogenchloride | |
With hydrogen bromide |
N-Chloroacetyl-D-phenylalanine
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride |
DL-N-benzoylphenylalanine
A
N-benzoyl-L-phenylalanine
B
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With D-amidase-substance from pseudomonas-cultures at 37℃; |
phthalic anhydride
D-(R)-phenylalanine
(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid
Conditions | Yield |
---|---|
for 0.05h; microwave irradiation; | 100% |
With pyridine for 12h; Heating; | 93% |
With triethylamine In toluene Heating; | 88% |
Conditions | Yield |
---|---|
With thionyl chloride | 100% |
With chloro-trimethyl-silane | 100% |
With thionyl chloride at 0 - 75℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With thionyl chloride for 4h; Reflux; | 100% |
With hydrogenchloride In toluene | |
With hydrogenchloride for 2h; Heating; | |
With thionyl chloride at 80℃; Cooling with ice; | |
With thionyl chloride at 20℃; |
Conditions | Yield |
---|---|
Stage #1: methanol With acetyl chloride at 0℃; for 0.5h; Stage #2: D-(R)-phenylalanine for 3h; Reflux; | 100% |
With hydrogenchloride for 0.166667h; Heating; | 88% |
With chlorosulfonic acid at 20℃; for 2h; | 76% |
D-(R)-phenylalanine
D-phenylalanine methyl ester hydrochloride
Conditions | Yield |
---|---|
With acetyl chloride at 70℃; Cooling; | 100% |
With thionyl chloride In methanol | 31.2 g (97%) |
Conditions | Yield |
---|---|
With sodium nitrite at 20℃; for 1.5h; Inert atmosphere; | 100% |
With sodium nitrite In water |
D-(R)-phenylalanine
acetyl chloride
D-phenylalanine methyl ester hydrochloride
Conditions | Yield |
---|---|
In methanol at 0 - 20℃; for 16h; Inert atmosphere; | 100% |
Stage #1: acetyl chloride In methanol Cooling with ice; Stage #2: D-(R)-phenylalanine In methanol at 70℃; for 24h; Reflux; |
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% |
Conditions | Yield |
---|---|
With sodium carbonate | 99% |
With sodium hydrogencarbonate In water at 20℃; for 12h; | 99% |
With sodium hydrogencarbonate; sodium hydroxide In water at 0 - 20℃; | 74% |
D-(R)-phenylalanine
Allyl chloroformate
(R)-(N-allyloxycarbonyl)phenylalanine
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 2h; Inert atmosphere; | 99% |
With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane | 80% |
With sodium carbonate In water; acetonitrile at 0 - 20℃; | 74% |
D-(R)-phenylalanine
D-phenyllactic acid
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite at 0 - 20℃; for 18h; | 98.5% |
With sulfuric acid; sodium nitrite for 36h; | 98% |
Stage #1: D-(R)-phenylalanine With sulfuric acid; sodium nitrite In water at 0 - 10℃; for 3h; Stage #2: With water at 10 - 20℃; | 87% |
Conditions | Yield |
---|---|
Stage #1: D-(R)-phenylalanine; perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride With 1H-imidazole at 120℃; for 0.5h; Stage #2: With hydrogenchloride In water at 85℃; pH=3 - 4; | 98% |
With 1H-imidazole at 140℃; for 1h; | 97% |
ethyl trifluoroacetate,
D-(R)-phenylalanine
(R)-N-(trifluoroacetyl)phenylalanine
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; | 98% |
Conditions | Yield |
---|---|
Stage #1: D-(R)-phenylalanine With sodium hydroxide In tetrahydrofuran; water for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; water at 20℃; for 24h; pH=Ca. 10.5; Inert atmosphere; Cooling with ice; | 97.2% |
With guanidine hydrochloride In ethanol at 35 - 40℃; for 6.5h; | 93% |
With amberlyst-15 In ethanol at 20℃; for 20h; chemoselective reaction; | 93% |
D-(R)-phenylalanine
cyclohexanylcarbonyl chloride
(R)-2-(cyclohexanecarboxamido)-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With potassium phosphate In tetrahydrofuran for 24h; Inert atmosphere; | 97% |
With sodium hydroxide In acetone | 65% |
Conditions | Yield |
---|---|
In acetic acid at 20℃; | 96% |
D-(R)-phenylalanine
Conditions | Yield |
---|---|
With triethylamine In water; acetonitrile at 20℃; for 12h; | 96% |
(R)-1-benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-one
D-(R)-phenylalanine
(R)-3-phenyl-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionylamino)propionic acid
Conditions | Yield |
---|---|
With triethylamine In water; acetonitrile at 20℃; for 12h; | 96% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol; water; acetone at 20℃; for 5h; | 96% |
N-(Benzyloxycarbonyloxy)succinimide
D-(R)-phenylalanine
N-cyclohexyl-cyclohexanamine
Conditions | Yield |
---|---|
Stage #1: N-(Benzyloxycarbonyloxy)succinimide; D-(R)-phenylalanine With sodium hydrogencarbonate; sodium carbonate In water; acetone at 20℃; for 3.5h; Stage #2: N-cyclohexyl-cyclohexanamine In water; ethyl acetate; acetone at 20℃; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 100℃; for 10h; | 96% |
D-(R)-phenylalanine
p-toluenesulfonyl chloride
Nα-(4-methylbenzenesulfonyl)-D-phenylalanine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 60℃; for 6h; | 95% |
With sodium hydroxide In diethyl ether at 20℃; for 6h; | 81% |
With sodium hydroxide In diethyl ether at 20℃; | 79% |
tritylsulfenyl chloride
D-(R)-phenylalanine
N-triphenylmethylsulfenyl-D-phenylalanine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 0.5h; Ambient temperature; | 95% |
D-(R)-phenylalanine
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
Fmoc-D-Phe-OH
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In acetone Ambient temperature; | 95% |
With sodium carbonate In aq. buffer at 37℃; for 10h; pH=8.0 - 9.0; |
D-Phenylalanine is an essential amino acid. With cas registry number of 673-06-3, it also has other registry number which is 10549-11-8. Its EINECS registry number is 211-603-5. This chemical is also known as Phenylalanine D-form with appearance of white crystalline powder. It is stable, but incompatible with strong oxidizing agents, acids, bases. It belongs to the categories in Benzene derivatives; Aromatic Propionic Acids; Phenylalanine [Phe, F]; Amino Acids and Derivatives; alpha-Amino Acids; Amino Acids; Biochemistry; Amino Acids; chemicals; organic acids; pharmaceutical intermediate; phenlalnine.
Physical properties about this chemical are: (1)ACD/LogP: 1.11; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.39; (4)ACD/LogD (pH 7.4): -1.39; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.576; (13)Molar Refractivity: 45.49 cm3; (14)Molar Volume: 137.4 cm3; (15)Surface Tension: 53.5 dyne/cm; (16)Density: 1.201 g/cm3; (17)Flash Point: 139.8 °C; (18)Enthalpy of Vaporization: 57.87 kJ/mol; (19)Boiling Point: 307.5 °C at 760 mmHg; (20)Vapour Pressure: 0.000313 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
Mildly toxic by intraperitoneal route. Human systemic effects by ingestion: nausea, hypermotility, diarrhea. When heated to decomposition, it emits toxic fumes of NOx. It can causes burns. Wear suitable protective clothing, gloves and eye/face protection during using it. Avoid contact with skin and eyes. Take off immediately all contaminated clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Or if you feel unwell, seek medical advice immediately.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@H](N)Cc1ccccc1;
(2)InChI: InChI=1/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m1/s1;
(3)InChIKey: COLNVLDHVKWLRT-MRVPVSSYBE
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
human | TDLo | oral | 500mg/kg/5W-I (500mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING | Journal of the American College of Toxicology. Vol. 1(3), Pg. 124, 1982. |
rat | LD50 | intraperitoneal | 5452mg/kg (5452mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Archives of Biochemistry and Biophysics. Vol. 64, Pg. 319, 1956. |
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