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CAS No.: | 68392-35-8 |
---|---|
Name: | Afimoxifene |
Article Data: | 9 |
Molecular Structure: | |
Formula: | C26H29 N O2 |
Molecular Weight: | 387.522 |
Synonyms: | Phenol,4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]- (9CI); 4-OHT; 4-[1-[4-[2-(Dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]phenol;Afimoxifene; TamoGel |
Density: | 1.092 |
Melting Point: | 135-144°C |
Boiling Point: | 514.4±50.0 °C(Predicted) |
Risk Codes: | 63-20/21/22 |
PSA: | 32.70000 |
LogP: | 5.70170 |
4-hydroxytamoxifen
Conditions | Yield |
---|---|
With water In methanol for 0.0333333h; Quantum yield; Photolysis; | 73% |
(2-chloroethyl)dimethylamine hydrochloride
1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene
4-hydroxytamoxifen
Conditions | Yield |
---|---|
Stage #1: 1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene With caesium carbonate In N,N-dimethyl-formamide for 0.5h; Reflux; Stage #2: (2-chloroethyl)dimethylamine hydrochloride In N,N-dimethyl-formamide at 120℃; for 7h; | 67% |
Stage #1: 1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene With caesium carbonate In N,N-dimethyl-formamide at 70 - 80℃; for 0.166667h; Stage #2: (2-chloroethyl)dimethylamine hydrochloride In N,N-dimethyl-formamide for 1.75h; | 30% |
Stage #1: 1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Stage #2: (2-chloroethyl)dimethylamine hydrochloride In N,N-dimethyl-formamide at 80℃; for 5.5h; | 13.6% |
Stage #1: 1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 0.166667h; Stage #2: (2-chloroethyl)dimethylamine hydrochloride In N,N-dimethyl-formamide at 80℃; for 5.5h; | 13.6% |
dimethyl amine
E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene
4-hydroxytamoxifen
Conditions | Yield |
---|---|
In tetrahydrofuran at 60℃; for 43h; | 31% |
1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene
2-(dimethylamino)ethyl chloride
4-hydroxytamoxifen
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide Inert atmosphere; | 24% |
Propylbenzene
4-hydroxytamoxifen
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium tert-butoxide; n-butyllithium; tetramethylethylenediamine / hexane; tetrahydrofuran / 0.5 h / 20 °C 1.2: 97 percent / hexane; tetrahydrofuran / 4.5 h / -78 - 20 °C 2.1: 93 percent / aq. hydrochloric acid / ethanol; CH2Cl2 / Heating 3.1: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C 4.1: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 5.1: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme |
4-hydroxy-4'-methoxybenzophenone
4-hydroxytamoxifen
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / dimethylformamide / 1 h / 0 °C 1.2: 95 percent / dimethylformamide / 2 h / 20 °C 2.1: potassium tert-butoxide; n-butyllithium; tetramethylethylenediamine / hexane; tetrahydrofuran / 0.5 h / 20 °C 2.2: 97 percent / hexane; tetrahydrofuran / 4.5 h / -78 - 20 °C 3.1: 93 percent / aq. hydrochloric acid / ethanol; CH2Cl2 / Heating 4.1: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C 5.1: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 6.1: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme |
4-(methoxymethoxy)-4'-methoxybenzophenone
4-hydroxytamoxifen
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium tert-butoxide; n-butyllithium; tetramethylethylenediamine / hexane; tetrahydrofuran / 0.5 h / 20 °C 1.2: 97 percent / hexane; tetrahydrofuran / 4.5 h / -78 - 20 °C 2.1: 93 percent / aq. hydrochloric acid / ethanol; CH2Cl2 / Heating 3.1: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C 4.1: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 5.1: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme |
E/Z-1-(4-hydroxyphenyl)-1-(4-methoxyphenyl)-2-phenylbutene
4-hydroxytamoxifen
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C 2: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 3: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme |
1-(4-methoxymethoxyphenyl)-1-(4-methoxyphenyl)-2-phenylbutan-1-ol
4-hydroxytamoxifen
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 93 percent / aq. hydrochloric acid / ethanol; CH2Cl2 / Heating 2: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C 3: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 4: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme |
E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-methoxyphenyl)-2-phenylbut-1-ene
4-hydroxytamoxifen
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 2: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme |
Molecular Structure of Afimoxifene (CAS NO.68392-35-8):
IUPAC Name: 4-[(Z)-1-[4-(2-Dimethylaminoethyloxy)phenyl]-2-phenylbut-1-enyl]phenol
Molecular Formula: C26H29NO2
Molecular Weight: 387.51
Index of Refraction: 1.596
Molar Refractivity: 120.77 cm3
Molar Volume: 354.6 cm3
Surface Tension: 43.9 dyne/cm
Density: 1.092 g/cm3
Flash Point: 264.9 °C
Enthalpy of Vaporization: 81.57 kJ/mol
Boiling Point: 514.4 °C at 760 mmHg
Vapour Pressure: 3.35E-11 mmHg at 25 °C
Canonical SMILES: CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3
Isomeric SMILES: CC/C(=C(\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3
InChI: InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
InChIKey: TXUZVZSFRXZGTL-QPLCGJKRSA-N
Classification Code: Estrogen Antagonists; Estrogen Receptor Modulators; Hormone Antagonists; Hormones, Hormone Substitutes, and Hormone Antagonists
Afimoxifene (CAS NO.68392-35-8) is a selective estrogen receptor modulator whose active ingredient is 4-Hydroxytamoxifen which is identical to the active metabolite of tamoxifen.
Afimoxifene (CAS NO.68392-35-8), its Synonyms are 4-Hydroxytamoxifen ; 4-(1-(4-(2-(Dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol ; Phenol, 4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenyl-1-butenyl)-, ; Phenol,4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]- ; Phenol,4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenyl-1-butenyl]- (9CI) ; 4-OHT ; TamoGel .