D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In hydrogenchloride at 55℃; under 760 Torr; | 100% |
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In water at 90℃; under 1500.15 Torr; | 92% |
With hydrogen; acetic acid; palladium on activated charcoal In water at 20℃; for 6h; |
methyl (2S)-4-phenyl-2-(trichloromethylcarbonylamino)butanoate
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride; water for 20h; Inert atmosphere; Reflux; | 100% |
Conditions | Yield |
---|---|
With formate dehydrogenase; NAD; ammonium formate at 30℃; for 24h; PheDH; | 99% |
With formate dehydrogenase; ammonium formate; β-nicotinamide adenine dinucleotide reduced In aq. buffer at 30℃; for 24h; pH=8.5; Enzymatic reaction; | 80% |
With L-phenylalanine; phenylalanine dehydrogenase; pyridoxal 5'-phosphate; alcohol dehydrogenases from Bacillus stearothermophilus; aromatic aminotransferase; NADH In isopropyl alcohol at 35℃; for 2h; pH=8; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | 60.3% |
With glucose dehydrogenase; ammonium sulfate; D-glucose; NADP+-specific glutamate dehydrogenase from Pseudomonas putida, K402F mutant; nicotinamide adenine dinucleotide phosphate In aq. buffer at 35℃; pH=7.5; Reagent/catalyst; Green chemistry; Enzymatic reaction; enantioselective reaction; | n/a |
(RS)-homophenylalaninamide hydrochloride
D-homophenylalanine
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate monohydrate; cobalt(II) chloride In aq. buffer at 40℃; for 12h; pH=7.0; Enzymatic reaction; | 99% |
D-homophenylalanine
Conditions | Yield |
---|---|
With sodium carbonate In methanol for 0.0833333h; | 98% |
(S)-2-Azido-4-phenyl-butyric acid
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethyl acetate under 760 Torr; for 13h; | 92% |
With hydrogen; palladium on activated charcoal In methanol |
(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-oxo-2'-phenylethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
A
D-homophenylalanine
B
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogen; palladium dichloride In tetrahydrofuran; ethanol under 2068.6 Torr; for 34h; Yields of byproduct given; | A 91% B n/a |
D-homophenylalanine
Conditions | Yield |
---|---|
With 10 wt% Pd(OH)2 on carbon; hydrogen In ethanol; water at 65℃; | 91% |
homophenylalanine sodium salt
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide In water | 89.6% |
D-homophenylalanine
Conditions | Yield |
---|---|
With 20% palladium hydroxide-activated charcoal; hydrogen In methanol at 45℃; under 760.051 Torr; for 7h; Reagent/catalyst; Inert atmosphere; Green chemistry; | 85% |
2-(acetylamino)-4-phenylbutanoic acid
A
D-homophenylalanine
B
(2R)-N-acetyl-2-amino-4-phenylbutyric acid
Conditions | Yield |
---|---|
With L-aminoacylase; cobalt(II) chloride In aq. buffer at 20 - 38℃; for 1h; pH=7.5; Inert atmosphere; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A 39% B 51% |
With sodium hydroxide; potassium phosphate buffer; beef kidney acetone; CoCl2 at 37℃; for 24h; pH=7.5; Enzymatic reaction; | A 41% B 37.5% |
With aminoacylase from Aspergillus oryzae; cobalt(II) chloride In water at 37℃; for 34h; | A 38% B 37% |
With cobalt(II) chloride at 30℃; pH=8; aq. phosphate buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogen; palladium dihydroxide In 1,4-dioxane; trifluoroacetic acid under 3102.89 Torr; | 50% |
Conditions | Yield |
---|---|
Stage #1: 4-Phenylbutyric acid With P450CLA; dihydrogen peroxide In aq. phosphate buffer; ethanol at 20℃; for 20h; pH=7; Enzymatic reaction; Stage #2: With D-HIC-DH; L-HIC-DH; L-Phe-DH; NAD; ammonium carbonate; ammonium chloride In aq. phosphate buffer; ethanol at 20℃; for 24h; pH=8; Enzymatic reaction; enantioselective reaction; | 48% |
Stage #1: 4-Phenylbutyric acid With P450CLA; dihydrogen peroxide In aq. phosphate buffer; ethanol at 20℃; for 24h; pH=7; Enzymatic reaction; Stage #2: With D-isocaproate dehydrogenase from Lactobacillus confuses; L-isocaproate dehydrogenase from Lactobacillus confuses; L-phenylalanine dehydrogenase from Rhodococcus sp.; NAD; ammonium carbonate; ammonium chloride In aq. phosphate buffer; ethanol for 24h; pH=8; Enzymatic reaction; enantioselective reaction; | 48% |
(R)-2-Acetamido-4-phenylbutansaeure
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride | |
With phosphoric acid |
1-styrenyloxytrimethylsilane
(5S,6R)-3-Bromo-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogen; zinc(II) chloride; palladium dichloride 1.) THF, 25 deg C, 2.) EtOH, 25 deg C, p= 20 psi; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With CoCl2 In water at 37℃; for 72h; aminoacylase (from Aspergillus oryzae); pH 7; | |
With aminoacylase I from Aspergillus melleus; Tris buffer In water at 25℃; pH=7.5; |
Conditions | Yield |
---|---|
With hydrogenchloride; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride Product distribution; various alkyl halides, stereoselective addition; |
-2-<(benzyloxycarbonyl)amino>-4-phenyl-3-butenoic acid
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol for 4h; Ambient temperature; |
[(E)-(S)-1-((S)-1,2-Dihydroxy-ethyl)-3-phenyl-allyl]-carbamic acid tert-butyl ester
D-homophenylalanine
Conditions | Yield |
---|---|
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile |
Conditions | Yield |
---|---|
With Alcalase; water In tert-butyl alcohol at 25℃; for 0.3h; pH=8.5; kinetic resolution; Title compound not separated from byproducts; |
D-homophenylalanine
Conditions | Yield |
---|---|
With aminopeptidase-substance from pig's-kidneys; water; manganese(ll) chloride at 38℃; pH 7.5; |
(S)-2-acetamido-4-phenylbutyric acid ethyl ester
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Hydrolysis; Heating; |
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogen; palladium dihydroxide In 1,4-dioxane; trifluoroacetic acid under 3102.89 Torr; |
DL-2-amino-4-phenylbutyramide
A
D-homophenylalanine
B
D-homophenylalanine
Conditions | Yield |
---|---|
With aminoacylase I from Aspergillus melleus; Tris buffer In water at 25℃; for 2.5h; pH=7.5; Title compound not separated from byproducts; | |
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 3 h / 20 °C 2: pyridoxal 5'-phosphate monohydrate / aq. buffer / 12 h / 40 °C / pH 8.0 / Enzymatic reaction View Scheme |
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogen; acetic acid; palladium on activated charcoal In water at 20℃; for 6h; |
D-homophenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: LHMDS / tetrahydrofuran; hexane / -78 °C 1.2: Br2 / tetrahydrofuran; hexane / -78 °C 2.1: 92 percent / tetramethylguanidinium azide / CH2Cl2 / 0 - 20 °C 3.1: 95 percent / LiOH; aq. H2O2 / tetrahydrofuran / 20 °C 4.1: H2 / Pd/C / methanol View Scheme |
(2'R,4S,5R)-1-(2'-bromo-4'-phenylbutyryl)-3,4-dimethyl-5-phenylimidazolidin-2-one
D-homophenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 92 percent / tetramethylguanidinium azide / CH2Cl2 / 0 - 20 °C 2: 95 percent / LiOH; aq. H2O2 / tetrahydrofuran / 20 °C 3: H2 / Pd/C / methanol View Scheme |
(4S,5R)-1-((S)-2-Azido-4-phenyl-butyryl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one
D-homophenylalanine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / LiOH; aq. H2O2 / tetrahydrofuran / 20 °C 2: H2 / Pd/C / methanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: alkaline aq. solution / 0.5 h / 4 °C / pH 11 2: aminoacylase I from Aspergillus melleus; Tris buffer / H2O / 25 °C / pH 7.5 View Scheme | |
Multi-step reaction with 2 steps 1: 89.5 percent / NaOH / H2O / 1 h / 0 - 5 °C / pH 11 - 11.5 2: 41 percent / potassium phosphate buffer; aq. NaOH; beef kidney acetone powder / CoCl2 / 24 h / 37 °C / pH 7.5 / Enzymatic reaction View Scheme | |
Multi-step reaction with 2 steps 2: CoCl2 / H2O / 72 h / 37 °C / aminoacylase (from Aspergillus oryzae); pH 7 View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / Cooling with ice 1.2: pH 2 2.1: penicillin G acylase from Achromobacter sp. CCM 4824; water / 30 °C / pH 7 / Enzymatic reaction View Scheme |
ethanol
D-homophenylalanine
L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; | 100% |
With thionyl chloride at 60℃; for 5h; | 92% |
With thionyl chloride |
D-homophenylalanine
methyl chloroformate
(S)-2-<(Methoxycarbonyl)amino>-4-phenylbutanoic Acid
Conditions | Yield |
---|---|
With sodium carbonate In water a) 0 deg C, 10 min, b) r.t., 2 h; | 100% |
In tetrahydrofuran; water; sodium carbonate | 97% |
With sodium carbonate In tetrahydrofuran at 20℃; for 4h; | 97% |
methanol
D-homophenylalanine
(+)-α-amino-4-phenylbutyric acid methyl ester hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride for 5h; Heating / reflux; | 100% |
With thionyl chloride at 0 - 65℃; for 2h; | 95% |
With thionyl chloride at 0 - 65℃; for 2h; | 95% |
With thionyl chloride at 0 - 20℃; |
D-homophenylalanine
(2S)-2-amino-4-phenyl-1-butanol
Conditions | Yield |
---|---|
With lithium borohydride; Methyltrichlorosilane In tetrahydrofuran at 0℃; for 18.5h; | 97% |
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 75% |
Stage #1: D-homophenylalanine With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 18h; Reflux; Stage #2: With water; sodium hydroxide In tetrahydrofuran |
D-homophenylalanine
Conditions | Yield |
---|---|
With hydrogenchloride; 5% rhodium-on-charcoal; platinum on carbon In methanol; water at 20℃; under 3102.97 Torr; | 97% |
With hydrogenchloride; sodium hydroxide In water | |
With hydrogenchloride; 5% platinum on carbon; 5% Rh/C; hydrogen In methanol; water under 3102.97 Torr; |
Conditions | Yield |
---|---|
In water at 3℃; Darkness; | 96% |
D-homophenylalanine
(S)-2-bromo-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With hydrogen bromide; sodium nitrite In water at -10℃; for 3h; | 94% |
2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate
D-homophenylalanine
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; water at 20℃; Condensation; | 89% |
D-homophenylalanine
Conditions | Yield |
---|---|
Stage #1: D-homophenylalanine With hydrogen bromide; sodium nitrite In water for 0.666667h; Stage #2: With sodium hydride; potassium thioacetate In N,N-dimethyl-formamide at 20℃; for 4h; Stage #3: With sodium hydroxide In methanol at 20℃; for 3h; | 89% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium carbonate | 84.9% |
D-homophenylalanine
ethyl acetate
2-oxo-4-phenylbutanoic acid ethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hypochlorite; tetrabutylammomium bromide In water at 0 - 40℃; Product distribution / selectivity; | 84.1% |
D-homophenylalanine
(S)-2-amino-4-cyclohexylbutyric acid hydrochloride
Conditions | Yield |
---|---|
With hydrogen; platinum In hydrogenchloride under 2585.7 Torr; for 16h; | 84% |
D-homophenylalanine
benzyl alcohol
benzyl (2S)-2-amino-4-phenylbutyrate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 16h; Dean-Stark; Reflux; | 80% |
D-homophenylalanine
toluene-4-sulfonic acid
benzyl alcohol
p-tolylsulfonic caid salt of L-homophenylalanine benzyl ester
Conditions | Yield |
---|---|
In toluene for 4h; Heating; | 79% |
In benzene for 6h; Heating; |
D-homophenylalanine
(S,S)-2,4-dibenzylglutaric anhydride
N-<(S,S)-2,4-dibenzyl-4-carboxybutyryl>-(S)-homophenylalanine
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 16h; Ambient temperature; | 74% |
D-homophenylalanine
Conditions | Yield |
---|---|
With triethylamine In isopropyl alcohol at 60℃; for 24h; Catalytic behavior; Concentration; Solvent; Temperature; | 73% |
phthalic anhydride
D-homophenylalanine
(S)-2-(1,3-dioxoisoindolin-2-yl)-4-phenylbutanoic acid
Conditions | Yield |
---|---|
With triethylamine In toluene at 130℃; Dean-Stark; | 72% |
D-homophenylalanine
L-4-nitro-homophenylalanine
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 0 - 5℃; for 0.5h; | 59% |
D-homophenylalanine
benzoyl chloride
(S)-2-benzoylamino-4-phenylbutyric acid
Conditions | Yield |
---|---|
With sodium hydroxide In water at 0 - 23℃; | 59% |
With sodium hydroxide cooling; |
The IUPAC name of L-Homophenylalanine is (2S)-2-amino-4-phenylbutanoic acid. With the CAS registry number 943-73-7, it is also named as (S)-alpha-Amino-benzenebutanoic acid. The product's categories are Phenylalanine Analogs and Other Aromatic alpha Amino Acids; API Intermediates; Homophenylalanine [Hph]; Amino Acids 13C, 2H, 15N; Chiral Compound; Amino Acids; Amino Acids & Derivatives; Aromatics. It is white solid which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place. When use it, people should not breathe dust and avoid contact with skin and eyes.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.97; (4)ACD/LogD (pH 7.4): -0.97; (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: 5; (12)Index of Refraction: 1.564; (13)Molar Refractivity: 50.12 cm3; (14)Molar Volume: 153.9 cm3; (15)Polarizability: 19.87×10-24 cm3; (16)Surface Tension: 51.1 dyne/cm; (17)Enthalpy of Vaporization: 59.84 kJ/mol; (18)Vapour Pressure: 9.79E-05 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Exact Mass: 179.094629; (21)MonoIsotopic Mass: 179.094629; (22)Topological Polar Surface Area: 63.3; (23)Heavy Atom Count: 13; (24)Complexity: 164; (25)Defined Atom StereoCenter Count: 1.
Preparation of L-Homophenylalanine: It can be obtained by (R)-2-acetylamino-4-phenyl-butyric acid. This reaction needs reagent 6 N aq. HCl by heating. The yield is 96%.
Uses of L-Homophenylalanine: It is used as antitumor agent. It also can react with ethanol to get R-(-)-Homophenylalanin-ethylester. This reaction needs reagent HCl and Na2CO3. The yield is 89%.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)C(N)CCc1ccccc1
2. InChI:InChI=1/C10H13NO2/c11-9(10(12)13)7-6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)
3. InChIKey:JTTHKOPSMAVJFE-UHFFFAOYAD
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