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554-52-9

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554-52-9 Usage

Uses

4-?(2-?Aminoethyl)?-?2-?methoxyphenol is a respective metabolite to dopamine and is being biologically study in Parkinson’s disease, and Wilms’ tumors.

Check Digit Verification of cas no

The CAS Registry Mumber 554-52-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 4 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 554-52:
(5*5)+(4*5)+(3*4)+(2*5)+(1*2)=69
69 % 10 = 9
So 554-52-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H13NO2/c1-6-7(4-5-10)2-3-8(11)9(6)12/h2-3,11-12H,4-5,10H2,1H3

554-52-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(2-Aminoethyl)-2-methoxyphenol

1.2 Other means of identification

Product number -
Other names Phenol, 4-(2-aminoethyl)-2-methoxy-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:554-52-9 SDS

554-52-9Synthetic route

2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethannitril
33630-46-5

2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethannitril

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
With sulfuric acid; hydrogen; 5%-palladium/activated carbon In methanol at 20 - 25℃; under 3750.38 Torr; for 4.33333h;86%
4-hydroxy-3-methoxyphenylacetonitrile
4468-59-1

4-hydroxy-3-methoxyphenylacetonitrile

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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;
vanillalnitromethane
6178-42-3

vanillalnitromethane

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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
63909-38-6, 1860-56-6

3-methoxy-4-benzyloxy-ω-nitrostyrolene

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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;
(4-acetoxy-3-methoxy-phenyl)-acetonitrile
5438-51-7

(4-acetoxy-3-methoxy-phenyl)-acetonitrile

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
With sulfuric acid; acetic acid; platinum Hydrogenation;
2-benzylamino-1-(4-hydroxy-3-methoxy-phenyl)-ethanone; hydrochloride

2-benzylamino-1-(4-hydroxy-3-methoxy-phenyl)-ethanone; hydrochloride

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
With palladium on activated charcoal; acetic acid Hydrogenation.zuletzt unter Zusatz von wss.HClO4, bei 80grad;
2-(3,4-dimethoxyphenyl)-ethylamine
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

A

3-Methoxytyramine
554-52-9

3-Methoxytyramine

B

5-(2-amino-ethyl)-2-methoxy-phenol
3213-30-7

5-(2-amino-ethyl)-2-methoxy-phenol

Conditions
ConditionsYield
With ammonia; sodium
dopamine
51-61-6

dopamine

A

3-Methoxytyramine
554-52-9

3-Methoxytyramine

B

5-(2-amino-ethyl)-2-methoxy-phenol
3213-30-7

5-(2-amino-ethyl)-2-methoxy-phenol

Conditions
ConditionsYield
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
83608-86-0, 78510-19-7

N-trans-feruloyl-3-O-methyldopamine

A

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

B

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
With sodium hydroxide
[2-(4-Benzyloxy-3-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester

[2-(4-Benzyloxy-3-methoxy-phenyl)-ethyl]-carbamic acid benzyl ester

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol
4-hydroxy-3-methoxy-DL-mandelonitrile

4-hydroxy-3-methoxy-DL-mandelonitrile

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
With hydrogenchloride; ethanol; platinum Hydrogenation;
With sulfuric acid; acetic acid Hydrogenation;
hydrochloride of 3-methoxy-4-benzyloxy-β-phenethylamine

hydrochloride of 3-methoxy-4-benzyloxy-β-phenethylamine

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
With hydrogenchloride
2-methoxy-4-(2-nitroethyl)phenol
528594-30-1

2-methoxy-4-(2-nitroethyl)phenol

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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
3-methoxy-4-(phenylmethoxy)benzaldehyde
2426-87-1

3-methoxy-4-(phenylmethoxy)benzaldehyde

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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
60372-07-8

1-(3-methoxy-4-benzyloxyphenyl)-2-nitroethanol

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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
vanillin
121-33-5

vanillin

<4-oxy-3-methoxy-phenyl>-bis-<4-dimethylamino-phenyl>-methane

<4-oxy-3-methoxy-phenyl>-bis-<4-dimethylamino-phenyl>-methane

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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
3,4-dimethoxyphenylacetonitrile
93-17-4

3,4-dimethoxyphenylacetonitrile

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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
22568-51-0

(E)-2-methoxy-4-(2-nitrovinyl)phenol

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4
2: H2 / Pd/C
View Scheme
4-benzyloxy-3-methoxyphenethylamine

4-benzyloxy-3-methoxyphenethylamine

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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
N-(4-benzyloxy-3-methoxyphenethyl)-4-benzyloxy-3-methoxycinnamide

N-(4-benzyloxy-3-methoxyphenethyl)-4-benzyloxy-3-methoxycinnamide

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 66.2 percent / aq. HCl, AcOH
2: 20percent aq. NaOH
View Scheme
dopamine
51-61-6

dopamine

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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
37034-22-3

N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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
87745-55-9

4-O-benzyl-N-benzyloxycarbonyldopamine

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether
2: H2 / Pd/C / ethanol
View Scheme
vanillin
121-33-5

vanillin

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
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
42973-53-5

2-methoxy-4-((methylamino)methyl)phenol

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide
2: H2, aq. HCl / Pd-C / ethanol
View Scheme
2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine
22231-61-4

2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
palladium on charcoal In tetrahydrofuran
3-Methoxytyramine hydrochloride
1477-68-5

3-Methoxytyramine hydrochloride

3-Methoxytyramine
554-52-9

3-Methoxytyramine

Conditions
ConditionsYield
With ammonium hydroxide In water at 50℃; pH=9 - 10;21.5 g
3-Methoxytyramine
554-52-9

3-Methoxytyramine

ortho-bromophenylacetic acid
18698-97-0

ortho-bromophenylacetic acid

2-(2-bromo-phenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide
634151-27-2

2-(2-bromo-phenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;100%
Octanoic acid
124-07-2

Octanoic acid

3-Methoxytyramine
554-52-9

3-Methoxytyramine

N-(4-hydroxy-3-methoxyphenethyl)octanamide

N-(4-hydroxy-3-methoxyphenethyl)octanamide

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 0 - 20℃; for 16h;95%
3-Methoxytyramine
554-52-9

3-Methoxytyramine

ortho-chlorobenzoic acid
118-91-2

ortho-chlorobenzoic acid

2-(4-hydroxy-3-methoxyphenethylamino)benzoic acid
1381802-03-4

2-(4-hydroxy-3-methoxyphenethylamino)benzoic acid

Conditions
ConditionsYield
With copper; potassium carbonate In ethyl methyl ether at 25 - 30℃; for 1.5h; Ullmann reaction; Inert atmosphere; Sonication;94%
3-Methoxytyramine
554-52-9

3-Methoxytyramine

demethyldihydrocorynantheine
75991-86-5

demethyldihydrocorynantheine

2-((2S,3R,12bS)-3-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-3-[(E)-2-(4-hydroxy-3-methoxy-phenyl)-ethylimino]-propionic acid methyl ester

2-((2S,3R,12bS)-3-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-3-[(E)-2-(4-hydroxy-3-methoxy-phenyl)-ethylimino]-propionic acid methyl ester

Conditions
ConditionsYield
In methanol for 4h; Ambient temperature;92%
3-Methoxytyramine
554-52-9

3-Methoxytyramine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>chloroacetamide
53527-13-2

N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>chloroacetamide

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran Ambient temperature;92%
homoisovanillic acid
1131-94-8

homoisovanillic acid

3-Methoxytyramine
554-52-9

3-Methoxytyramine

N-(β-4-hydroxy-3-methoxyphenethyl)-(3-hydroxy-4-methoxyphenyl)acetamide
21411-19-8

N-(β-4-hydroxy-3-methoxyphenethyl)-(3-hydroxy-4-methoxyphenyl)acetamide

Conditions
ConditionsYield
Heating;90.4%
3-Methoxytyramine
554-52-9

3-Methoxytyramine

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

N-ethoxycarbonyl-4-hydroxy-3-methoxyphenethylamine

N-ethoxycarbonyl-4-hydroxy-3-methoxyphenethylamine

Conditions
ConditionsYield
With triethylamine; sodium hydroxide90%
3-Methoxytyramine
554-52-9

3-Methoxytyramine

2-bromo-5-methoxy-benzoic acid
22921-68-2

2-bromo-5-methoxy-benzoic acid

C17H19NO5
1381802-91-0

C17H19NO5

Conditions
ConditionsYield
With copper; potassium carbonate In ethyl methyl ether at 25 - 30℃; for 1.5h; Ullmann reaction; Inert atmosphere; Sonication;89%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3-Methoxytyramine
554-52-9

3-Methoxytyramine

tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate
23699-77-6

tert-butyl 4-hydroxy-3-methoxyphenethylcarbamate

Conditions
ConditionsYield
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
554-52-9

3-Methoxytyramine

3-benzyloxy-4-methoxybenzoyl chloride
41222-60-0

3-benzyloxy-4-methoxybenzoyl chloride

N-(4-hydroxy-3-methoxyphenethyl)-4-methoxy-3-benzyloxybenzamide
113332-61-9

N-(4-hydroxy-3-methoxyphenethyl)-4-methoxy-3-benzyloxybenzamide

Conditions
ConditionsYield
With water; sodium carbonate In chloroform for 18h; Ambient temperature;86%
phthalic anhydride
85-44-9

phthalic anhydride

3-Methoxytyramine
554-52-9

3-Methoxytyramine

N-[2-(3-methoxy-4-hydroxy-phenyl)ethyl]phthalimide
37627-79-5

N-[2-(3-methoxy-4-hydroxy-phenyl)ethyl]phthalimide

Conditions
ConditionsYield
With boron tribromide In toluene Dean-Stark; Reflux;86%
2-(2-propynyloxy)-2-(4-chlorophenyl)-acetic acid
655223-09-9

2-(2-propynyloxy)-2-(4-chlorophenyl)-acetic acid

3-Methoxytyramine
554-52-9

3-Methoxytyramine

2-(4-chloro-phenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-prop-2-ynyloxyacetamide

2-(4-chloro-phenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-prop-2-ynyloxyacetamide

Conditions
ConditionsYield
In xylene at 143℃; for 4h; Product distribution / selectivity; Inert atmosphere; Molecular sieve;83%
succinic acid anhydride
108-30-5

succinic acid anhydride

3-Methoxytyramine
554-52-9

3-Methoxytyramine

N-[2-(3-methoxy-4-hydroxyphenyl)ethyl]succinimide

N-[2-(3-methoxy-4-hydroxyphenyl)ethyl]succinimide

Conditions
ConditionsYield
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
554-52-9

3-Methoxytyramine

peperomin E

peperomin E

(2S,3S)-6-(4'''-hydroxy-5'''-methoxyphenethylamino)-2,6-dihydropeperomin E

(2S,3S)-6-(4'''-hydroxy-5'''-methoxyphenethylamino)-2,6-dihydropeperomin E

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 18h; Inert atmosphere;80%
4,5-dichlorothieno[2,3-d]pyrimidine

4,5-dichlorothieno[2,3-d]pyrimidine

3-Methoxytyramine
554-52-9

3-Methoxytyramine

4-{2-[(5-chlorothieno[2,3-d]pyrimidin-4-yl)amino]ethyl}-2-methoxyphenol
935252-62-3

4-{2-[(5-chlorothieno[2,3-d]pyrimidin-4-yl)amino]ethyl}-2-methoxyphenol

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide76%
With triethylamine In N,N-dimethyl-formamide76%
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
1169605-26-8

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
554-52-9

3-Methoxytyramine

4-(2-((9-((3aR,3bR,4aS,5R,5aS)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-yl)-2-iodo-9Hpurin-6-yl)amino)ethyl)-2-methoxyphenol

4-(2-((9-((3aR,3bR,4aS,5R,5aS)-2,2-dimethylhexahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxol-5-yl)-2-iodo-9Hpurin-6-yl)amino)ethyl)-2-methoxyphenol

Conditions
ConditionsYield
In isopropyl alcohol at 75℃; for 1h; Microwave irradiation;75%
3-Methoxytyramine
554-52-9

3-Methoxytyramine

benzaldehyde
100-52-7

benzaldehyde

6-methoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-7-ol
72105-97-6

6-methoxy-1-phenyl-1,2,3,4-tetrahydro-isoquinolin-7-ol

Conditions
ConditionsYield
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
554-52-9

3-Methoxytyramine

(S)-N-(methylsulphonyl)valine
97482-31-0

(S)-N-(methylsulphonyl)valine

(S)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-methanesulfonylamino-3-methyl-butyramide
189946-12-1

(S)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-2-methanesulfonylamino-3-methyl-butyramide

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine71%
2,5-dibromobenzoic acid
610-71-9

2,5-dibromobenzoic acid

3-Methoxytyramine
554-52-9

3-Methoxytyramine

C16H16BrNO4
1381802-57-8

C16H16BrNO4

Conditions
ConditionsYield
With copper; potassium carbonate In ethyl methyl ether at 25 - 30℃; for 1h; Ullmann reaction; Inert atmosphere; Sonication;71%
2,4-dodecadienoic acid
24738-48-5

2,4-dodecadienoic acid

3-Methoxytyramine
554-52-9

3-Methoxytyramine

(2E,4E)-N-(4-hydroxy-3-methoxyphenethyl)dodeca-2,4-dienamide

(2E,4E)-N-(4-hydroxy-3-methoxyphenethyl)dodeca-2,4-dienamide

Conditions
ConditionsYield
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
554-52-9

3-Methoxytyramine

(2-Chloro-5-hydroxy-4-methoxy-phenyl)-acetic acid methyl ester
81038-50-8

(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
81038-52-0

2-(2-Chloro-5-hydroxy-4-methoxy-phenyl)-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide

Conditions
ConditionsYield
at 160℃;63%
3-Methoxytyramine
554-52-9

3-Methoxytyramine

6-chloro-2-((5-chlorothiophen-2-yl)ethynyl)-9H-purine

6-chloro-2-((5-chlorothiophen-2-yl)ethynyl)-9H-purine

2-((5-chlorothiophen-2-yl)ethynyl)-N-(4-hydroxy-3-methoxyphenethyl)-9H-purin-6-amine

2-((5-chlorothiophen-2-yl)ethynyl)-N-(4-hydroxy-3-methoxyphenethyl)-9H-purin-6-amine

Conditions
ConditionsYield
With triethylamine In ethanol Reflux;63%
p-Coumaric Acid
7400-08-0

p-Coumaric Acid

3-Methoxytyramine
554-52-9

3-Methoxytyramine

N-trans-p-coumaroyl-3-O-methyldopamine
1246613-34-2

N-trans-p-coumaroyl-3-O-methyldopamine

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;62%
5-benzyloxy-2-bromo-4-methoxyphenylacetic acid
13425-04-2

5-benzyloxy-2-bromo-4-methoxyphenylacetic acid

3-Methoxytyramine
554-52-9

3-Methoxytyramine

N-(4'-benzyloxy-3'-methoxyphenylethyl)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)acetamide
892805-32-2

N-(4'-benzyloxy-3'-methoxyphenylethyl)-2-(2-bromo-5-hydroxy-4-methoxyphenyl)acetamide

Conditions
ConditionsYield
at 180℃; for 3h;61%
3-Methoxytyramine
554-52-9

3-Methoxytyramine

<3,4-bis(benzyloxy)phenyl>acetic acid
1699-61-2

<3,4-bis(benzyloxy)phenyl>acetic acid

2-<3',4'-bis(benzyloxy)phenyl>-N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>acetamide
138645-00-8

2-<3',4'-bis(benzyloxy)phenyl>-N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>acetamide

Conditions
ConditionsYield
at 185 - 190℃; for 2h;60.4%
3-Methoxytyramine
554-52-9

3-Methoxytyramine

Homovanillic acid
306-08-1

Homovanillic acid

(4'-hydroxy-3'-methoxyphenyl)-N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>acetamide
138645-09-7

(4'-hydroxy-3'-methoxyphenyl)-N-<2-(4-hydroxy-3-methoxyphenyl)ethyl>acetamide

Conditions
ConditionsYield
for 2h; Heating;59.3%
at 200℃; for 4h; Inert atmosphere;
3-Methoxytyramine
554-52-9

3-Methoxytyramine

trans-3-hydroxy-4-methoxycinnamic acid
537-73-5

trans-3-hydroxy-4-methoxycinnamic acid

N-trans-4-O-methylcaffeoyl-3'-O-methyldopamine

N-trans-4-O-methylcaffeoyl-3'-O-methyldopamine

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran Ambient temperature;59%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;48%
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

3-Methoxytyramine
554-52-9

3-Methoxytyramine

N-trans-feruloyl-3-O-methyldopamine
83608-86-0, 78510-19-7

N-trans-feruloyl-3-O-methyldopamine

Conditions
ConditionsYield
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;

554-52-9Relevant articles and documents

TARGETED BIFUNCTIONAL DEGRADERS

-

, (2021/04/17)

The present invention provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In another aspect, the present invention provides bifunctional compounds that can be used to promote or enhance degradation of certain autoantibodies. In certain embodiments, treatment or management of a disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein or the autoantibody in the subject. Thus, in certain embodiments, administration of a compound of the invention to the subject removes or reduces the circulation concentration of the circulating protein or the autoantibody, thus treating, ameliorating, or preventing the disease and/or disorder. In certain embodiments, the circulating protein is TNF.

Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

Nagasawa, Shota,Fujiki, Shogo,Sasano, Yusuke,Iwabuchi, Yoshiharu

, p. 6952 - 6968 (2021/05/29)

We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

SUBSTITUTED 1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE MOLECULES AS PCSK9 ALLOSTERIC BINDERS

-

, (2018/04/20)

The present invention relates to PCSK9 allosteric binding compounds of Formula I: (Formula (I)) and pharmaceutically acceptable salts thereof, wherein X1, X2, Y, R1, R2, RA, RB and n are as defined herein. The present invention also relates to compositions which comprise an allosteric binding compound of the invention or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. The invention further relates, inter alia, to methods for inducing PCSK9 protein degradation in a subject, and methods for treating atherosclerosis, hypercholesterolemia, coronary heart disease, metabolic syndrome, acute coronary syndrome, or related cardiovascular disease and cardiometabolic conditions, comprising administering to a subject an effective amount of a compound or a pharmaceutically acceptable salt of the invention. The invention also provides a means for the in vitro labeling, detection and/or quantification of PCSK9 in biological samples.

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