N-acetamido cinnamic acid
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With hydrogen; triethylamine; [Rh(CLPL-S)(COD)]BF4 In methanol at 40℃; under 15001.5 Torr; for 22h; Product distribution / selectivity; | 100% |
In ethanol | 98% |
With hydrogen; [Rh(norbornadiene)2]BF4 In methanol at 30℃; under 750.06 Torr; | 96% |
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
96.2% |
N-acetamido cinnamic acid
A
(R)-N-acetylphenylalanin
B
(S)-2-acetylamino-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With [Rh(cod)(Xylophos)](1+)*BF4(1-); hydrogen In methanol at 19.85℃; under 760 Torr; for 6h; | A 11% B 89% |
With hydrogen; (1+); Dowex HCR-S In methanol; water at 50℃; under 15001.2 Torr; Product distribution; other rhodium(I)-complexes, various reaction conditions: time, pressure and temperatures; other derivatives of acetamidoacryl acid; | |
With hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer; optically active phosphine In methanol at 20 - 30℃; under 825.07 Torr; for 72h; Product distribution; various di- and triphosphines, other temperatures and times; |
N-acetylphenylalanine methyl ester
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
for 36h; carbonate hydrolyase EC 4.2.2.1 (bovine carbonic anhydrase, BCA), pH 7.5; | 81% |
ethyl N-acetyl-DL-phenylalaninate
A
(R)-N-acetylphenylalanin
B
(S)-2-acetylamino-3-phenylpropanoic acid
C
(R)-ethyl N-acetylphenylalanine
Conditions | Yield |
---|---|
With water In ethanol at 25℃; for 2h; Microbiological reaction; optical yield given as %ee; enantioselective reaction; | A n/a B n/a C 45% |
at 35℃; for 48h; in the present of Saccharomyces cerevisiae Hansen; Yield given. Yields of byproduct given; |
D-phenylalanine hydrochloride
acetyl chloride
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With sodium hydroxide; water at 0℃; for 1h; | 41% |
(R,S)-N-acetyl phenylalanine
(1S)-endo-fenchylamine
(R)-N-acetylphenylalanin
(R,S)-N-acetyl phenylalanine
(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With sodium hydroxide | |
at 0 - 4℃; for 3h; Acetylation; | |
With sodium hydroxide In water at 0 - 25℃; for 0.5h; pH=11 - 12; | |
With sodium hydroxide In water at 20℃; pH=14; |
Conditions | Yield |
---|---|
With papain |
2-methyl-4-benzyl-4H-oxazolin-5-one
A
(R)-N-acetylphenylalanin
B
(S)-2-acetylamino-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With alpha cyclodextrin In water; acetonitrile pH 7.86; Title compound not separated from byproducts; |
2-(N-acetylamino)cinnamic acid
A
(R)-N-acetylphenylalanin
B
(S)-2-acetylamino-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With hydrogen In methanol at 25℃; under 3150.3 Torr; for 4h; Product distribution; enantioselectivity of reaction dependent on various rhodium complexes with 1,2-bis(phosphanyl)pyrrolidine ligands; various conditions; also N-acetylcinnamic acid methylester; | |
With 2S-MeN(PPh2)CHC7H7CH2OPPh2; hydrogen; Rh<(COD)Cl>2 Product distribution; other reagents; | |
With hydrogen; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; Br>n In ethanol at 20℃; Product distribution; asymmetric catalytic hydrogenation, enantiodifferentiating ability of the catalysts: atmospheric pressure of H2; var. catalysts, pressure, temp. and initial rate; |
N-acetyl dehydrophenylalanine methyl ester
A
(R)-N-acetylphenylalanin
B
(S)-2-acetylamino-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate In methanol at 22℃; under 38000 Torr; Product distribution; various substrate/catalyst molar ratio; modifications of the catalyst; |
methyl (Z)-2-(acetylamino)-3-phenylpropenoate
A
(R)-N-acetylphenylalanin
B
(S)-2-acetylamino-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With hydrogen; tetrafluoroboric acid; Rh complex from Rh(COD)acac; (R,R)-4,5-bis(diphenylphosphinomethyl)-2-methyl-2-phenyl-1,3-dioxolane under 760 Torr; Title compound not separated from byproducts; |
(R,S)-N-acetyl phenylalanine
A
L-phenylalanine
B
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl2; | |
With sodium hydroxide; Tris buffer; acylase (immobilized, cross-linking enzyme membrane) In N,N-dimethyl-formamide at 40℃; pH=8.0; Enzyme kinetics; Further Variations:; pH-values; Temperatures; Solvents; Enzymatic reaction; | |
With lipase AS 'Amano' at 35℃; for 24h; pH=6.5; Catalytic behavior; Concentration; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | A n/a B n/a |
(E)-α-(N-acylamino)cinnamic acid
A
N-acetamido cinnamic acid
B
(R)-N-acetylphenylalanin
C
(S)-2-acetylamino-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With hydrogen; triethylamine; <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3 In tetrahydrofuran; ethanol at 35℃; under 1520 Torr; for 24h; Title compound not separated from byproducts; |
(E)-α-(N-acylamino)cinnamic acid
A
(R)-N-acetylphenylalanin
B
(S)-2-acetylamino-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With hydrogen; triethylamine; <((R)-(1,1'-binaphthyl-2,2'-diyl)bis(diphenylphosphine))RuCl2>2NEt3 In tetrahydrofuran; ethanol at 35℃; under 1520 Torr; for 24h; RuHCl-bis<(R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl>, with and without Et3N; Title compound not separated from byproducts; | |
With hydrogen; +ClO4- In ethanol at 20℃; under 760 Torr; for 0.5h; | |
With hydrogen; chlorobis(ethylene)rhodium(I) dimer; +ClO4- In ethanol at 20℃; under 760 Torr; for 0.5h; |
N-acetyl-D-phenylalanine 4-nitrophenyl ester
A
4-nitro-phenol
B
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
PalHis; PalHis + 2C14N2C1Br In water; acetonitrile at 25℃; Rate constant; furhter bilayer catalytic systems; kcat; | |
With Nα-tetradecanoyl-L-histidine In water; acetonitrile at 10℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.); Tris-KCl buffer, didodecyldimethylammonium bromide; other nucleophiles and surfactants; other temp.; | |
With water; poly(iminomethylene); cetylpyridinium chloride at 23℃; Rate constant; pH 5.6; different poly(iminomethylene) 1-cetylpyridinium complexes catalysts and pH-s; | |
With Z-L-Leu-L-His-L-Leu; Tris buffer; N,N-didodecyl-N,N-dimethylammonium bromide In acetonitrile at 24.9℃; Rate constant; pH: 7.68, μ = 0.15 (KCl); other peptide catalyst; binding constants Kb/N; |
N-acetyl-D-phenylalanine 4-nitrophenyl ester
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With N,N-dimethyl-N-tetradecyltetradecan-1-aminium bromide; N-tetradecanoyl-L-histidyl-L-leucine In water; acetonitrile at 10 - 45℃; Kinetics; other dialkyldimethylammonium bromides; |
N-acetyl-D-phenylalanine 4-nitrophenyl ester
A
(R)-N-acetylphenylalanin
B
p-nitrophenolate
Conditions | Yield |
---|---|
With Z-L-Leu-L-His-L-Leu; N,N-didodecyl-N,N-dimethylammonium bromide; water In acetonitrile at 25℃; Rate constant; kL/kD, Kb (binding constant); |
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With pH 7.0; subtilisin Carlsberg In water at 30℃; Kinetics; further enzymes; |
sodium α-(acetylamino)cinnamate
A
(R)-N-acetylphenylalanin
B
(S)-2-acetylamino-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With hydrogen; <(3R,4R)-3,4-bis(diphenylphosphino)-1,1-dimethylpyrrolidinium-P,P'>(1,5-cyclooctadiene)rhodium bis(tetrafluoroborate) In water at 22℃; under 36775.4 Torr; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With hydrogen; Ru(BINAP)(cymene) In water at 60℃; under 20701.7 Torr; for 92h; Product distribution; Further Variations:; Catalysts; Temperatures; Pressures; |
Conditions | Yield |
---|---|
With sodium carbonate buffer at 37℃; Rate constant; |
N-acetylphenylalanine methyl ester
A
(R)-N-acetylphenylalanin
B
(S)-2-acetylamino-3-phenylpropanoic acid
C
(R)-N-acetylphenylalanine methyl ester
Conditions | Yield |
---|---|
With subtilisin-CLEC In acetone at 40℃; for 0.5h; pH 7.0, phosphate buffer; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
butyl 2-acetylamino-3-phenylpropanoate
A
(R)-N-acetylphenylalanin
B
(S)-2-acetylamino-3-phenylpropanoic acid
Conditions | Yield |
---|---|
With rice bran lipase; sodium chloride at 30℃; pH=7.5; Title compound not separated from byproducts; |
(R,S)-N-acetyl phenylalanine
(R)-N-acetylphenylalanin
(R,S)-N-acetyl phenylalanine
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With p-toluidine |
2-(N-acetylamino)cinnamic acid
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With hydrogen; [((1R,2S)-DPAMPP)Rh(COD)]BF4 In methanol at 25℃; under 38000 Torr; for 1h; Catalytic hydrogenation; | |
With (+)-2,6'-bis(diphenylphosphino)-2'-methoxy-1,1'-biphenyl; hydrogen; bis(benzene)dichloro-ruthenium In methanol at 40℃; under 37503.8 Torr; for 16h; | n/a |
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (11bM)-4-((1R,2S)-1-(diphenylphosphino)-3-methoxy-1-phenylprop-2-yloxy)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine; hydrogen In tetrahydrofuran at 20℃; under 15001.5 Torr; for 12h; Autoclave; optical yield given as %ee; enantioselective reaction; |
(R)-N-acetylphenylalanin
(R)-2-acetamido-3-cyclohexylpropanoic acid
Conditions | Yield |
---|---|
With tetrahydroxydiboron; [Rh(OH)(cod)]2 In ethanol at 50℃; for 18h; Schlenk technique; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
In chloroform Inert atmosphere; | 97% |
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With N,N'-diethylurea; copper(II) bis(trifluoromethanesulfonate); triethylamine In tetrahydrofuran at 50℃; for 16h; Chan-Lam Coupling; | 93% |
(R)-N-acetylphenylalanin
D-Tryptophan methyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide | 84% |
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With sodium tetrahydroborate; iodine In tetrahydrofuran Heating; | 83% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide | 82% |
(R)-N-acetylphenylalanin
methyl (3S)-3-amino-3-(3,4-dimethoxyphenyl)propanoate
methyl (S)-3-amino-3-(3,4-dimethoxyphenyl)propionate N-acetyl-D-phenylalanine salt
Conditions | Yield |
---|---|
In methanol at 20℃; for 4h; Heating / reflux; | 82% |
(R)-N-acetylphenylalanin
D-threonine benzyl ester
(2R,3R)-2-((R)-2-Acetylamino-3-phenyl-propionylamino)-3-hydroxy-butyric acid benzyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane for 18h; Ambient temperature; | 70% |
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
Stage #1: (R)-N-acetylphenylalanin With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: C33H29N5O5S*C2HF3O2 In dichloromethane at 20℃; for 5h; Inert atmosphere; | 70% |
(R)-N-acetylphenylalanin
1-benzyl-2,2-dimethoxyethylamine
B
(S)-1-benzyl-2,2-dimethoxyethylammonium N-acetyl-D-phenylalaninate
Conditions | Yield |
---|---|
In isopropyl alcohol at 40 - 50℃; for 5h; | A 35% B 62% |
(R)-N-acetylphenylalanin
4-hydroxy-benzaldehyde
Conditions | Yield |
---|---|
With TEA; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6h; | 53% |
(R)-N-acetylphenylalanin
4-(BOC-tyrosylamino)piperidine
4-(BOC-tyrosylamino)-1-(N-acetyl-D-phenylalanyl)piperidine
Conditions | Yield |
---|---|
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In chloroform | 49% |
(1S,2S,3R,4S)-3-Amino-1,2,3,4-tetrahydro-1,4-methano-naphthalene-2-carboxylic acid ((S)-1-methylcarbamoyl-2-phenyl-ethyl)-amide
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; | 48% |
(R)-N-acetylphenylalanin
1,1-dimethylethylenediamine
(R)-2-Acetylamino-N-(2-amino-2-methyl-propyl)-3-phenyl-propionamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide Ambient temperature; | 46% |
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
In ethanol Reflux; | 43% |
3-methoxy-2-aminopropionic acid
(R)-N-acetylphenylalanin
Conditions | Yield |
---|---|
In methanol; water at 50℃; | 25% |
(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 |
(R)-N-acetylphenylalanin
4-[bis-(2-chloro-ethyl)-amino]-DL-phenylalanine ethyl ester; monohydrochloride
Conditions | Yield |
---|---|
With triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran |
The N-Acetyl-D-phenylalanine, with the CAS registry number 10172-89-1, is also known as (R)-2-(Acetylamino)-3-phenylpropanoic acid. It belongs to the product categories of Amino Acid Derivatives; Amino Acids; Ac-Amino Acids; Amino Acids (N-Protected); Biochemistry; A - H; Modified Amino Acids; Amino Acids & Derivatives; Chiral Reagents. Its EINECS number is 233-447-7. This chemical's molecular formula is C11H13NO3 and molecular weight is 207.23. What's more, its systematic name is N-Acetyl-D-phenylalanine. This chemical should be sealed and stored in a cool and dry place. It is a kind of chiral chemical raw material and it is used as pharmaceutical intermediates. It is also used in biochemical research.
Physical properties of N-Acetyl-D-phenylalanine are: (1)ACD/LogP: -1.022; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.27; (4)ACD/LogD (pH 7.4): -4.63; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 66.4 Å2; (13)Index of Refraction: 1.548; (14)Molar Refractivity: 54.848 cm3; (15)Molar Volume: 172.709 cm3; (16)Polarizability: 21.744×10-24cm3; (17)Surface Tension: 48.4 dyne/cm; (18)Density: 1.2 g/cm3; (19)Flash Point: 228.338 °C; (20)Enthalpy of Vaporization: 75.179 kJ/mol; (21)Boiling Point: 453.944 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@H](NC(=O)C)Cc1ccccc1
(2)Std. InChI: InChI=1S/C11H13NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,12,13)(H,14,15)/t10-/m1/s1
(3)Std. InChIKey: CBQJSKKFNMDLON-SNVBAGLBSA-N
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