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CAS No.: | 13002-65-8 |
---|---|
Name: | 2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethyl-ethanamine |
Article Data: | 31 |
Molecular Structure: | |
Formula: | C26H29 N O |
Molecular Weight: | 371.522 |
Synonyms: | Ethanamine,2-[4-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-, (E)-; Ethanamine, 2-[4-[(1E)-1,2-diphenyl-1-butenyl]phenoxy]-N,N-dimethyl-(9CI); Ethylamine, 2-[p-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-, (E)-(8CI); (E)-Tamoxifen; cis-Tamoxifen |
Density: | 1.0630 (rough estimate) |
Melting Point: | 72-74° from methanol |
Boiling Point: | 501.18°C (rough estimate) |
Safety: | Experimental reproductive effects. Human systemic effects: nausea or vomiting. When heated to decomposition it emits acrid smoke and irritating vapors. |
PSA: | 12.47000 |
LogP: | 5.99610 |
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; toluene at 80 - 85℃; for 3h; Inert atmosphere; | 97% |
With sodium ethanolate In ethanol for 24h; Heating; | 62% |
With sodium hydride 1.) DMF, 2.) 60 deg C, 30 min; Yield given. Multistep reaction; |
[2-(4-iodophenoxy)ethyl]dimethylamine
(Z)-2-(1,2-diphenylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
(E)-tamoxifen
Conditions | Yield |
---|---|
With sodium hydroxide; bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 60℃; for 24h; Suzuki-Miyaura coupling; | 95% |
With sodium hydroxide; bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 60℃; for 24h; Suzuki-Miyaura coupling; | 95% |
iodobenzene
(Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene
(E)-tamoxifen
Conditions | Yield |
---|---|
With sodium hydroxide; bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 60℃; for 24h; | 75% |
(4-(2-(dimethylamino)ethoxy)phenyl)magnesium bromide
(E)-tamoxifen
Conditions | Yield |
---|---|
With N,N'-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene hydrochloride; palladium diacetate In tetrahydrofuran at 50℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube; stereoselective reaction; | 70% |
(E)-1,2-diphenyl-1-butene boronic acid
[2-(4-bromophenoxy)ethyl]dimethylamine
A
1,2-diphenyl-butan-1-one
B
tamoxifen
C
(E)-tamoxifen
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water Suzuki-Miyaura cross-coupling; Heating; | A n/a B 65% C n/a |
N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethanamine
(E)-tamoxifen
Conditions | Yield |
---|---|
Stage #1: (2R,3R)-2-ethyl-2,3-diphenyloxirane With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.25h; Stage #2: N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethanamine In diethyl ether at 20 - 38℃; | 63% |
2-(dimethylamino)ethyl chloride
(E,Z)-4-(1,2-diphenylbut-1-en-1-yl)phenol
A
tamoxifen
B
(E)-tamoxifen
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 50℃; for 0.5h; | A 51% B 44% |
With sodium hydride In N,N-dimethyl-formamide at 50℃; for 0.5h; |
A
tamoxifen
B
(E)-tamoxifen
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 1h; | A 39% B 37% |
(1-phenylpropyl)phosphonic acid di-o-tolyl ester
(4-(2-(dimethylamino)ethoxy)phenyl)(phenyl)methanone
A
tamoxifen
B
(E)-tamoxifen
Conditions | Yield |
---|---|
Stage #1: (1-phenylpropyl)phosphonic acid di-o-tolyl ester With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: (4-(2-(dimethylamino)ethoxy)phenyl)(phenyl)methanone In tetrahydrofuran; hexane at -78℃; for 48h; Horner reaction; | A 28% B 12% |
tamoxifen
(E)-tamoxifen
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 4h; Heating; |
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IUPAC Name:2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine
Molecular Formula:C26H29NO
Molecular Weight:371.51456
Synonyms of (E)-TAMOXIFEN (13002-65-8):2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethyl-ethanamine;CIS-TAMOXIFEN;(E)-1,2-Diphenyl-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-butene;(E)-α-[4-[2-(Dimethylamino)ethoxy]phenyl]-β-ethylstilbene;2-[4-[(E)-1,2-Diphenyl-1-butenyl]phenoxy]-N,N-dimethylethaneamine;N,N-Dimethyl-2-[4-[(E)-1,2-diphenyl-1-butenyl]phenoxy]ethanamine;N,N-Dimethyl-2-[p-[(E)-1,2-diphenyl-1-butenyl]phenoxy]ethanamine
1. | orl-wmn TDLo:4 mg/kg/5D-I:GIT | BJCPAT British Journal of Clinical Practice. 44 (1990),716. |