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inquiryEstrone 3-methyl ether CAS No.:1624-62-0 Name: Estrone 3-methyl ether Synonyms: 3-Methoxy-1,3,5(10)-estratrien-17-one Molecular Structure Molecular Formula: C19H24O2 Molecular
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inquiryName:Estrone3-methylether The alias:NSC88911 CAS NO:1624-62-0 EINECS NO:216-613-3 Molecular formula:C19H24O2 Molecular weight:284.39 Product Quality 12 years of chemical raw materials Mature operation of the industry System stability Da
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estrone 3-methyl ether
Conditions | Yield |
---|---|
With water; potassium carbonate In methanol at 20℃; for 4h; Hydrolysis; | 100% |
With potassium carbonate In methanol; water at 20℃; for 18h; Product distribution; Further Variations:; Reagents; Solvents; pH-values; Hydrolysis; | 92% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; sodium hydroxide In dichloromethane at 70℃; for 3h; | 99% |
With potassium carbonate In N,N-dimethyl-formamide Heating; | 98% |
With potassium carbonate In N,N-dimethyl-formamide 1) reflux, 2 h, 2) r.t., 5 d; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 16h; | 99% |
17,17-ethylenedioxy-3-methoxyoestra-1,3,5(10)-triene
estrone 3-methyl ether
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; for 2h; | 98.3% |
With hydrogenchloride In water; acetone |
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone for 2h; Reflux; | 98% |
With sodium hydride In tetrahydrofuran at 0 - 20℃; | 97% |
With sodium hydride In tetrahydrofuran at 20℃; for 2h; | 97% |
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In N,N-dimethyl-formamide at 23 - 25℃; for 4h; | 98% |
With 1-hydroxy-1.oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one pyridinium salt In tetrahydrofuran at 24 - 28℃; for 24h; | 95% |
With oxone; C18H17IN2O7PolS(1-)*Na(1+); tetra(n-butyl)ammonium hydrogensulfate In acetonitrile at 70℃; for 18h; Sealed tube; Green chemistry; | 61% |
Multi-step reaction with 2 steps 1: 96 percent / pyridine / 24 h 2: 28 percent / KOAc / dimethylsulfoxide / 6 h / 100 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / benzene / 12 h / Ambient temperature 2: NaN3, water / acetone / 1 h / Heating 3: 35 percent / CCl4 / 6 h / 100 °C View Scheme |
estradiol 3-methyl ether, 17-ol
estrone 3-methyl ether
Conditions | Yield |
---|---|
With diisopropyl-carbodiimide In toluene at 120℃; for 24h; Inert atmosphere; Sealed tube; | 96% |
With Dess-Martin periodane In dichloromethane at 20℃; for 3h; Inert atmosphere; | 1.26 g |
estrone 3-methyl ether
Conditions | Yield |
---|---|
With oxygen; sodium methylate; silver trifluoromethanesulfonate In tetrahydrofuran; methanol at 37℃; for 12h; | 94% |
3-O-methyl-estra-1,3,5(10),6-tetraen-17-one
estrone 3-methyl ether
Conditions | Yield |
---|---|
With hydrogen In tetrahydrofuran at 20℃; for 1.5h; Catalytic behavior; Solvent; Time; | 93% |
Conditions | Yield |
---|---|
With caesium carbonate In 1,2-dimethoxyethane at 145℃; for 2h; Microwave irradiation; Inert atmosphere; Sealed vessel; | 90% |
{5-Methoxy-2-[3-((1S,5S)-1-methyl-2-oxo-5-vinyl-cyclopentyl)-1-trimethylsilanyl-propyl]-benzyl}-trimethyl-ammonium; iodide
estrone 3-methyl ether
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile for 1.5h; Heating; | 86% |
Conditions | Yield |
---|---|
Stage #1: 3-methoxy-estra-1,3,5(10),8(9),14(15)-pentaene-17-one With palladium 10% on activated carbon; hydrogen In benzene at 0℃; for 12h; Stage #2: With triethylsilane; trifluoroacetic acid In benzene at 20℃; for 13h; stereoselective reaction; | 82% |
Stage #1: 3-methoxy-estra-1,3,5(10),8(9),14(15)-pentaene-17-one With triethylsilane; palladium 10% on activated carbon; hydrogen In benzene at 0℃; for 20h; Stage #2: With tetra-(n-butyl)ammonium iodide; trifluoroacetic acid In dichloromethane at 0℃; for 5h; | 71% |
19-acetoxyandrosta-1,4-diene-3,17-dione
trimethyl orthoformate
estrone 3-methyl ether
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol at 60℃; for 1h; | 82% |
17β-hydroxy-3-methoxy-1,3,5(10),14-estratetraene
A
3-O-methyl-17β-oestradiol
B
estrone 3-methyl ether
C
3-methoxy-14β-1,3,5(10)-estratriene-17β-ol
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol for 10h; Ambient temperature; | A 5% B 3% C 81% |
Conditions | Yield |
---|---|
With potassium carbonate; phosphonium resin In dichloromethane; water; N,N-dimethyl-formamide for 120h; Ambient temperature; | 73% |
Conditions | Yield |
---|---|
With triethylsilane; trifluoroacetic acid In benzene for 12h; Ambient temperature; | 73% |
With triethylsilane; trifluoroacetic acid In dichloromethane; benzene | 65% |
With chromium(VI) oxide; aniline 1) liq. NH3, 2) acetone, H2O 1 h, r. t.; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With lithiumnaphthalide (0.66 M in THF) In tetrahydrofuran at 25℃; for 0.5h; | A 73% B 13% |
(+)-3-methoxy-17β-2-(quinolinylmethoxy)-estra-1,3,5(10)-triene
A
3-methoxy-13α-estra-1,3,5(10)-trien-17-one
B
estrone 3-methyl ether
Conditions | Yield |
---|---|
In acetonitrile for 4h; Irradiation; | A 12% B 72% |
(2S,3S)-2-[2-(3-Methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-ethyl]-2-methyl-3-vinyl-cyclopentanone
estrone 3-methyl ether
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene at 180℃; | 70% |
Conditions | Yield |
---|---|
With copper(ll) bromide; trimethyl orthoformate for 0.666667h; Heating; | 70% |
Conditions | Yield |
---|---|
With potassium dichromate; supported on AlPO-BPO In diethyl ether for 0.75h; Ambient temperature; | 54% |
methanol
estra-4-ene-3,17-dione
A
3-O-methylestra-1,3,5(10)-trien-3-ol-6,17-dione
B
estrone 3-methyl ether
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; iodine for 2h; Heating; | A 27% B 48% |
With iodine; ammonium cerium (IV) nitrate for 2h; Heating / reflux; | A 40% B 47% |
With copper(ll) bromide for 1h; Heating; | A n/a B 39% |
17α-trimethylsilylacetylenyl-3-methoxy-1,3,5(10)-estratrien-17β-ol
estrone 3-methyl ether
Conditions | Yield |
---|---|
With dicarbonylcyclopentadienylcobalt In xylene for 12h; Heating; | 48% |
3-methoxyestra-1,3,5(10)-trien-17β-yl p-toluenesulfonate
potassium acetate
A
3-methoxy-1,3,5(10)-estratrien-17α-ol
B
3-methoxy-17ξ-methylestra-1,3,5(10),13-tetraene
C
estrone 3-methyl ether
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 100℃; for 6h; Mechanism; Product distribution; also in the presence of acetic acid and without DMSO.; | A 45% B 26% C 28% |
3-methoxyestra-1,3,5(10)-trien-17β-yl p-toluenesulfonate
A
3-methoxy-1,3,5(10)-estratrien-17α-ol
B
3-methoxy-17ξ-methylestra-1,3,5(10),13-tetraene
C
estrone 3-methyl ether
Conditions | Yield |
---|---|
With potassium acetate In dimethyl sulfoxide at 100℃; for 6h; | A 45% B 26% C 28% |
Conditions | Yield |
---|---|
With dicarbonylcyclopentadienylcobalt In xylene at 140℃; for 2.5h; | A 44% B 12% |
(8R,9S,13S,14S,17S)-3-methoxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro(cyclopenta[a]phenanthrene-17,2'-oxirane)
estrone 3-methyl ether
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane for 5h; Ambient temperature; | 40% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In methanol; hexane; acetonitrile for 18h; Ambient temperature; | 38% |
4-(Dimethylamino)azoestrone 3-Methyl Ether
A
estrone 3-methyl ether
B
4,6-Diazaethenoestrone 3-Methyl Ether
Conditions | Yield |
---|---|
With pyridine hydrogenfluoride In benzene 1.) room temperature, 30 min, 2.) 50 deg C, 10 min; | A 15% B 36% |
estrone 3-methyl ether
Conditions | Yield |
---|---|
With sodium acetate In methanol Reflux; | 100% |
estrone 3-methyl ether
ethylene glycol
17,17-ethylenedioxy-3-methoxyoestra-1,3,5(10)-triene
Conditions | Yield |
---|---|
Stage #1: ethylene glycol With boron trifluoride diethyl etherate; orthoformic acid triethyl ester at 25℃; for 0.25h; Stage #2: estrone 3-methyl ether In dichloromethane at 25℃; for 5h; | 99% |
With toluene-4-sulfonic acid; orthoformic acid triethyl ester at 70℃; for 1h; | 99% |
With toluene-4-sulfonic acid In benzene for 12h; | |
With toluene-4-sulfonic acid |
Conditions | Yield |
---|---|
Stage #1: 1,3-diethynylbenzene With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: estrone 3-methyl ether In tetrahydrofuran at -50℃; for 3h; Inert atmosphere; | 99% |
methylmagnesium bromide
estrone 3-methyl ether
(8R,9S,13S,14S,17S)-3-methoxy-13,17-dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol
Conditions | Yield |
---|---|
In diethyl ether; benzene for 2h; Inert atmosphere; Reflux; | 99% |
In tetrahydrofuran; diethyl ether at 0 - 20℃; Schlenk technique; Inert atmosphere; | 69% |
Conditions | Yield |
---|---|
Stage #1: triphenylmethylhydrazine hydrochloride With sodium acetate trihydrate In methanol; water Inert atmosphere; Stage #2: estrone 3-methyl ether In methanol; dichloromethane; water at 22 - 26℃; for 336h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: estrone 3-methyl ether With lithium hexamethyldisilazane In tetrahydrofuran; toluene at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: cinnamyl tert-butyl carbonate With bis(η3-allyl-μ-chloropalladium(II)); potassium tert-butylate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran; toluene at 20℃; for 24h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With N,N'-Dimethylurea; tris(pyrrolidino)phosphine oxide; lithium bromide In tetrahydrofuran Electrochemical reaction; | 99% |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 15h; Heating; | 98.63% |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 14h; Heating; | 98.63% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; | 98% |
With potassium 2-methylbutan-2-olate |
t-butyldimethylsiyl triflate
estrone 3-methyl ether
tert-Butyl-((8R,9S,13S,14S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yloxy)-dimethyl-silane
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 0.25h; | 98% |
methyl cyanoformate
estrone 3-methyl ether
Conditions | Yield |
---|---|
With N-t-butylethylamine In tetrahydrofuran at 20℃; for 18h; Addition; | 98% |
With diisopropylamine In tetrahydrofuran at 20℃; for 24h; Product distribution; Further Variations:; Reagents; Temperatures; Solvents; reaction time; water presence; concentration of reaction partners; Addition; | 92% |
estrone 3-methyl ether
trimethylsilylacetylene
17α-trimethylsilylacetylenyl-3-methoxy-1,3,5(10)-estratrien-17β-ol
Conditions | Yield |
---|---|
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -40 - -20℃; for 1h; Inert atmosphere; Stage #2: estrone 3-methyl ether In tetrahydrofuran; hexane at -40 - 20℃; for 1.5h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water | 98% |
N,N-phenylbistrifluoromethane-sulfonimide
estrone 3-methyl ether
(8R,9S,13S,14S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 2h; | 98% |
trifluoromethylsulfonic anhydride
estrone 3-methyl ether
(8R,9S,13S,14S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 20℃; for 12h; | 97% |
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane | 88% |
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 20℃; for 1h; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With ethylene glycol; N1-butyl-N2,N2,N3,N3-tetramethylguanidine at 50℃; for 4h; Claisen-Schmidt Condensation; Inert atmosphere; Schlenk technique; | 97% |
With potassium hydroxide In ethanol at 100℃; for 0.333333h; Claisen-Schmidt Condensation; Microwave irradiation; | 497 mg |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 23h; Heating; | 96.77% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol; water at 20℃; for 72h; Inert atmosphere; | 96% |
With methanol; sodium tetrahydroborate In dichloromethane at 50℃; for 1h; | 94% |
With sodium tetrahydroborate In methanol at 50℃; for 2h; | 92% |
estrone 3-methyl ether
formic acid ethyl ester
16-(hydroxymethylene)-3-methoxyestra-1,3,5(10)-trien-17-one
Conditions | Yield |
---|---|
With sodium methylate In benzene for 4h; Heating; | 96% |
With sodium methylate In benzene | 93% |
With sodium hydride In benzene | |
With sodium methylate In benzene | |
With sodium methylate In benzene for 4h; Reflux; |
tert-butyldimethylsilyl cyanide
estrone 3-methyl ether
Conditions | Yield |
---|---|
zinc(II) iodide In dichloromethane at 25℃; for 2.5h; | 95% |
estrone 3-methyl ether
3-Methoxy-estra-1,3,5(10)-trien-17-on-hydrazone
Conditions | Yield |
---|---|
With hydrazine hydrate; triethylamine In ethanol | 95% |
With hydrazine hydrate; triethylamine In ethanol for 6h; Inert atmosphere; Reflux; | |
With hydrazine |
estrone 3-methyl ether
carbonic acid dimethyl ester
(8R,9S,13S,14S)-methyl 7,8,9,11,12,13,14,15,16,17-decahydro-3-methoxy-13-methyl-17-oxo-6H-cyclopenta[a]phenanthrene-16-carboxylate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran Heating; | 95% |
With methanol; sodium hydride for 3h; Reflux; | 95% |
With potassium hydride In tetrahydrofuran; mineral oil at 75℃; Inert atmosphere; | 81% |
With potassium hydride In tetrahydrofuran for 3h; Heating; | 78% |
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