2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethannitril
3-Methoxytyramine
Conditions | Yield |
---|---|
With sulfuric acid; hydrogen; 5%-palladium/activated carbon In methanol at 20 - 25℃; under 3750.38 Torr; for 4.33333h; | 86% |
Conditions | Yield |
---|---|
With hydrogen; Ra-Ni In ethanol; ammonia at 70℃; under 6080 - 7600 Torr; | 79% |
With ammonia; hydrogen; Ra-Ni catalyst In ethanol at 70℃; under 7600 Torr; | 75% |
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol | |
With hydrogenchloride; ammonium hydroxide; borane Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In 1,4-dioxane at 60℃; | 25% |
With 1,4-dioxane; Pd-BaSO4; sulfuric acid Hydrogenation; | |
With acetic acid; platinum Hydrogenation; |
3-methoxy-4-benzyloxy-ω-nitrostyrolene
3-Methoxytyramine
Conditions | Yield |
---|---|
With palladium on activated charcoal; ethanol Hydrogenation.unter Zusatz von wenig konz.wss.HCl; | |
With formic acid; palladium In ethanol at 18 - 20℃; for 5h; |
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid; platinum Hydrogenation; |
3-Methoxytyramine
Conditions | Yield |
---|---|
With palladium on activated charcoal; acetic acid Hydrogenation.zuletzt unter Zusatz von wss.HClO4, bei 80grad; |
2-(3,4-dimethoxyphenyl)-ethylamine
A
3-Methoxytyramine
B
5-(2-amino-ethyl)-2-methoxy-phenol
Conditions | Yield |
---|---|
With ammonia; sodium |
Conditions | Yield |
---|---|
at 37℃; for 15h; Product distribution; catechol-o-methyltransferase in crude liver homogenate, phosphate-citrate buffer, pH 4.4; |
N-trans-feruloyl-3-O-methyldopamine
A
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
B
3-Methoxytyramine
Conditions | Yield |
---|---|
With sodium hydroxide |
3-Methoxytyramine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol |
3-Methoxytyramine
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol; platinum Hydrogenation; | |
With sulfuric acid; acetic acid Hydrogenation; |
3-Methoxytyramine
Conditions | Yield |
---|---|
With hydrogenchloride |
2-methoxy-4-(2-nitroethyl)phenol
3-Methoxytyramine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal | |
With palladium 10% on activated carbon; hydrogen In ethanol at 50℃; under 2327.23 Torr; for 16h; | |
With palladium on activated charcoal | |
With hydrogenchloride; zinc In ethanol; water for 3h; | |
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; | 860 mg |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 71 percent / KOH, tetrabutylammonium bromide / ethanol / 1 h / 0 °C 2: 85 percent / AcONa. Ac2O / 0.08 h / Heating 3: formic acid / Pd black / ethanol / 5 h / 18 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 72 percent / KOH / aq. ethanol / 2 h / 0 °C 2: formic acid / Pd black / ethanol / 5 h / 18 - 20 °C View Scheme |
1-(3-methoxy-4-benzyloxyphenyl)-2-nitroethanol
3-Methoxytyramine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / AcONa. Ac2O / 0.08 h / Heating 2: formic acid / Pd black / ethanol / 5 h / 18 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 100 percent / K2CO3, tetrabutylammonium bromide / dimethylformamide / 5 h / 18 - 20 °C 2: 71 percent / KOH, tetrabutylammonium bromide / ethanol / 1 h / 0 °C 3: 85 percent / AcONa. Ac2O / 0.08 h / Heating 4: formic acid / Pd black / ethanol / 5 h / 18 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: 100 percent / K2CO3, tetrabutylammonium bromide / dimethylformamide / 5 h / 18 - 20 °C 2: 72 percent / KOH / aq. ethanol / 2 h / 0 °C 3: formic acid / Pd black / ethanol / 5 h / 18 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: AlCl3 / toluene 1.2: Br2; AcOH / CH2Cl2 / -78 °C 2.1: 75 percent / NH3; H2 / Ra-Ni catalyst / ethanol / 70 °C / 7600 Torr View Scheme |
(E)-2-methoxy-4-(2-nitrovinyl)phenol
3-Methoxytyramine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaBH4 2: H2 / Pd/C View Scheme |
3-Methoxytyramine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.5 h / 180 °C 2: 66.2 percent / aq. HCl, AcOH 3: 20percent aq. NaOH View Scheme |
3-Methoxytyramine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 66.2 percent / aq. HCl, AcOH 2: 20percent aq. NaOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 2 N NaOH / toluene; H2O / 2 h / 5 - 10 °C 2: 13 percent / NaHCO3 / ethanol / 16 h / Heating 3: diethyl ether 4: H2 / Pd/C / ethanol View Scheme |
N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine
3-Methoxytyramine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 13 percent / NaHCO3 / ethanol / 16 h / Heating 2: diethyl ether 3: H2 / Pd/C / ethanol View Scheme |
4-O-benzyl-N-benzyloxycarbonyldopamine
3-Methoxytyramine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether 2: H2 / Pd/C / ethanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / NH4(OAc) / acetic acid / Heating 2: 25 percent / DIBAH / dioxane / 60 °C View Scheme | |
Multi-step reaction with 3 steps 1: (i) EtOH, (ii) H2, PtO2 2: dimethylformamide 3: H2, aq. HCl / Pd-C / ethanol View Scheme | |
Multi-step reaction with 2 steps 2: H2, aq. HCl / Pd-C View Scheme |
2-methoxy-4-((methylamino)methyl)phenol
3-Methoxytyramine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dimethylformamide 2: H2, aq. HCl / Pd-C / ethanol View Scheme |
2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine
3-Methoxytyramine
Conditions | Yield |
---|---|
palladium on charcoal In tetrahydrofuran |
Conditions | Yield |
---|---|
With ammonium hydroxide In water at 50℃; pH=9 - 10; | 21.5 g |
3-Methoxytyramine
ortho-bromophenylacetic acid
2-(2-bromo-phenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h; | 100% |
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 0 - 20℃; for 16h; | 95% |
3-Methoxytyramine
ortho-chlorobenzoic acid
2-(4-hydroxy-3-methoxyphenethylamino)benzoic acid
Conditions | Yield |
---|---|
With copper; potassium carbonate In ethyl methyl ether at 25 - 30℃; for 1.5h; Ullmann reaction; Inert atmosphere; Sonication; | 94% |
3-Methoxytyramine
demethyldihydrocorynantheine
Conditions | Yield |
---|---|
In methanol for 4h; Ambient temperature; | 92% |
3-Methoxytyramine
chloroacetyl chloride
N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>chloroacetamide
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran Ambient temperature; | 92% |
homoisovanillic acid
3-Methoxytyramine
N-(β-4-hydroxy-3-methoxyphenethyl)-(3-hydroxy-4-methoxyphenyl)acetamide
Conditions | Yield |
---|---|
Heating; | 90.4% |
Conditions | Yield |
---|---|
With triethylamine; sodium hydroxide | 90% |
Conditions | Yield |
---|---|
With copper; potassium carbonate In ethyl methyl ether at 25 - 30℃; for 1.5h; Ullmann reaction; Inert atmosphere; Sonication; | 89% |
di-tert-butyl dicarbonate
3-Methoxytyramine
tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate
Conditions | Yield |
---|---|
With sodium hydroxide In 1,4-dioxane; water at 20℃; | 88% |
With triethylamine In chloroform at 20℃; for 24h; | 59% |
With triethylamine In methanol for 2h; | 57.5% |
With triethylamine In chloroform at 20℃; for 24h; |
3-Methoxytyramine
3-benzyloxy-4-methoxybenzoyl chloride
N-(4-hydroxy-3-methoxyphenethyl)-4-methoxy-3-benzyloxybenzamide
Conditions | Yield |
---|---|
With water; sodium carbonate In chloroform for 18h; Ambient temperature; | 86% |
phthalic anhydride
3-Methoxytyramine
N-[2-(3-methoxy-4-hydroxy-phenyl)ethyl]phthalimide
Conditions | Yield |
---|---|
With boron tribromide In toluene Dean-Stark; Reflux; | 86% |
2-(2-propynyloxy)-2-(4-chlorophenyl)-acetic acid
3-Methoxytyramine
Conditions | Yield |
---|---|
In xylene at 143℃; for 4h; Product distribution / selectivity; Inert atmosphere; Molecular sieve; | 83% |
Conditions | Yield |
---|---|
Stage #1: succinic acid anhydride; 3-Methoxytyramine In ethyl acetate at 20℃; for 0.5h; Stage #2: With acetyl chloride In toluene for 1h; Reflux; | 82% |
3-Methoxytyramine
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 18h; Inert atmosphere; | 80% |
3-Methoxytyramine
4-{2-[(5-chlorothieno[2,3-d]pyrimidin-4-yl)amino]ethyl}-2-methoxyphenol
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide | 76% |
With triethylamine In N,N-dimethyl-formamide | 76% |
6-chloro-9-((3aR,3bR,4aS,5R,5aS)-hexahydro-2,2dimethylbicyclo[3.1.0]hex-1(5)-eno[3,2-d] [1,3]dioxol-5-yl)-2-iodo-9H-purine
3-Methoxytyramine
Conditions | Yield |
---|---|
In isopropyl alcohol at 75℃; for 1h; Microwave irradiation; | 75% |
3-Methoxytyramine
benzaldehyde
6-methoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-7-ol
Conditions | Yield |
---|---|
Stage #1: 3-Methoxytyramine; benzaldehyde With magnesium sulfate; triethylamine In methanol for 3h; Heating / reflux; Stage #2: With trifluoroacetic acid for 1h; Heating / reflux; | 74% |
3-Methoxytyramine
(S)-N-(methylsulphonyl)valine
(S)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-methanesulfonylamino-3-methyl-butyramide
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine | 71% |
Conditions | Yield |
---|---|
With copper; potassium carbonate In ethyl methyl ether at 25 - 30℃; for 1h; Ullmann reaction; Inert atmosphere; Sonication; | 71% |
2,4-dodecadienoic acid
3-Methoxytyramine
Conditions | Yield |
---|---|
Stage #1: 2,4-dodecadienoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.166667h; Stage #2: 3-Methoxytyramine With triethylamine In dichloromethane at 20℃; | 69% |
3-Methoxytyramine
(2-Chloro-5-hydroxy-4-methoxy-phenyl)-acetic acid methyl ester
2-(2-Chloro-5-hydroxy-4-methoxy-phenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide
Conditions | Yield |
---|---|
at 160℃; | 63% |
3-Methoxytyramine
Conditions | Yield |
---|---|
With triethylamine In ethanol Reflux; | 63% |
p-Coumaric Acid
3-Methoxytyramine
N-trans-p-coumaroyl-3-O-methyldopamine
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; | 62% |
5-benzyloxy-2-bromo-4-methoxyphenylacetic acid
3-Methoxytyramine
N-(4'-benzyloxy-3'-methoxyphenylethyl)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)acetamide
Conditions | Yield |
---|---|
at 180℃; for 3h; | 61% |
3-Methoxytyramine
<3,4-bis(benzyloxy)phenyl>acetic acid
2-<3',4'-bis(benzyloxy)phenyl>-N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>acetamide
Conditions | Yield |
---|---|
at 185 - 190℃; for 2h; | 60.4% |
3-Methoxytyramine
Homovanillic acid
(4'-hydroxy-3'-methoxyphenyl)-N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>acetamide
Conditions | Yield |
---|---|
for 2h; Heating; | 59.3% |
at 200℃; for 4h; Inert atmosphere; |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran Ambient temperature; | 59% |
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; | 48% |
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
3-Methoxytyramine
N-trans-feruloyl-3-O-methyldopamine
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; | 56% |
With dicyclohexyl-carbodiimide In tetrahydrofuran Ambient temperature; | 55% |
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With triethylamine In N,N-dimethyl-formamide for 0.25h; Cooling with ice; Stage #2: 3-Methoxytyramine With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; |
Molecular Structure of Phenol,4-(2-aminoethyl)-2-methoxy- (CAS No. 554-52-9):
Systematic Name: 4-(2-Aminoethyl)-2-methoxyphenol
Synonyms: 4-(2-Aminoethyl)-2-methoxyphenol ; 3-Methoxy-4-hydroxyphenethylamine
Molecular Formula: C9H13NO2
Molecular Weight: 167.20
CAS Registry Number: 554-52-9
Index of Refraction: 1.559
Molar Refractivity: 47.898 cm3
Molar Volume: 148.36 cm3
Surface Tension: 45.155 dyne/cm
Density: 1.127 g/cm3
Flash Point: 137.95 °C
Enthalpy of Vaporization: 56.662 kJ/mol
Boiling Point: 304.489 °C at 760 mmHg
Structure Descriptors of Phenol,4-(2-aminoethyl)-2-methoxy- (CAS No. 554-52-9):
SMILES: COc1cc(ccc1O)CCN
InChI: InChI=1/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3
InChIKey: DIVQKHQLANKJQO-UHFFFAOYAB
Std. InChI: InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3
Std. InChIKey: DIVQKHQLANKJQO-UHFFFAOYSA-N
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