17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
exemestane
Conditions | Yield |
---|---|
With Jones reagent In acetone at -20℃; Jones oxidation; Inert atmosphere; | 100% |
With jones reagent In acetone at -20℃; for 0.25h; | 85% |
With Jones reagent In acetone at 0℃; Product distribution / selectivity; |
6α-hydroxymethylandrosta-1,4-diene-3,17-dione
exemestane
Conditions | Yield |
---|---|
Stage #1: 6α-hydroxymethylandrosta-1,4-diene-3,17-dione With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 30℃; Stage #2: With methanol; potassium hydroxide at 40 - 50℃; | 90% |
exemestane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In water; acetone at 25 - 30℃; for 10h; Solvent; Reagent/catalyst; Temperature; Jones Oxidation; Inert atmosphere; | 88.2% |
6-methylene-androst-4-ene 3,17-dione
exemestane
Conditions | Yield |
---|---|
With N,O-Bis(trimethylsilyl)trifluoroacetamide; chloranil; trifluorormethanesulfonic acid In toluene at 108 - 110℃; for 0.75h; Product distribution / selectivity; Heating / reflux; | 81.8% |
With trifluorormethanesulfonic acid; N,O-Bis(trimethylsilyl)trifluoroacetamide; chloranil In toluene Inert atmosphere; Reflux; | 81% |
With tert-butyldimethylsilyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 0 - 20℃; | 30.2% |
Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; for 24h; | A 8% B 60% |
6-Methylen-4-androsten-3,17-dion
exemestane
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide; toluene at 85℃; for 48h; Inert atmosphere; Large scale; | 56.7% |
Androsta-1,4-diene-3,17-dione
exemestane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 20 h / Heating 2: 1.10 g / benzene; ethanol; H2O / 5 h / 20 °C 3: 60 percent / conc. HCl / 24 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; sodium acetate / water; ethanol / 6 h / Inert atmosphere; Reflux 2.1: N,N-dimethylammonium chloride / i-Amyl alcohol / 2 h / Inert atmosphere; Reflux 2.2: 15 h / 140 °C 3.1: toluene-4-sulfonic acid / water; acetone / 10 h / 25 - 30 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / tetrahydrofuran / 12 h / 40 - 45 °C / Large scale 2: tetrahydrofuran; ethanol / 10 h / 40 - 45 °C / Large scale 3: hydrogenchloride / tetrahydrofuran; ethanol / 1 h / Large scale 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; toluene / 48 h / 85 °C / Inert atmosphere; Large scale View Scheme |
1α,3-dipyrrolidinylandrosta-3,5-dien-17-one
exemestane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.10 g / benzene; ethanol; H2O / 5 h / 20 °C 2: 60 percent / conc. HCl / 24 h / 20 °C View Scheme |
1-dehydrotestosterone
exemestane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) Me2NH*HCl / 1.) isoamyl alcohol, reflux, 2 h, 2.) isoamyl alcohol, reflux, 15 h 2: 85 percent / Jones reagent / acetone / 0.25 h / -20 °C View Scheme |
C21H28O5S
exemestane
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; dichloromethane; water at 25℃; Heating / reflux; |
pyrographite
6-methylene-androst-4-ene 3,17-dione
tert-butyl alcohol
exemestane
Conditions | Yield |
---|---|
With selenium(IV) oxide In ethyl acetate |
exemestane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 80 - 90℃; under 315 Torr; for 4h; Purification / work up; | |
With toluene-4-sulfonic acid In toluene at 90℃; for 3h; Purification / work up; | |
With camphor-10-sulfonic acid In toluene at 90℃; for 7h; Purification / work up; | |
With (1S)-10-camphorsulfonic acid In ethyl acetate at 70 - 80℃; for 32h; Purification / work up; | |
Stage #1: 6-hydroxymethyl-androsta-1,4-diene-3,17-dione With pyridine; p-toluenesulfonyl chloride at 0℃; for 48h; Stage #2: With potassium hydroxide In methanol; water at 65℃; for 2h; Purification / work up; |
dehydroepiandrosterone
exemestane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: toluene / 1 h / 120 °C / Inert atmosphere 1.2: 0.33 h / 20 °C / Inert atmosphere 1.3: 3 h / 20 °C / Inert atmosphere 2.1: orthoformic acid triethyl ester; toluene-4-sulfonic acid / ethanol; tetrahydrofuran / 3 h / 40 °C 2.2: 4 h / 40 °C 3.1: Arthrobacter simplex ATCC6946 culture / aq. buffer / 33 °C / Microbiological reaction View Scheme |
3-Aethoxy-androstadien-(3,5)-on-(17)
exemestane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrahydrofuran; ethanol / 10 h / 40 - 45 °C / Large scale 2: hydrogenchloride / tetrahydrofuran; ethanol / 1 h / Large scale 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; toluene / 48 h / 85 °C / Inert atmosphere; Large scale View Scheme |
exemestane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In tetrahydrofuran; water at 20 - 25℃; for 10h; Inert atmosphere; |
exemestane
FCE27353
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 48h; Ambient temperature; | 80% |
exemestane
Conditions | Yield |
---|---|
With copper(l) iodide; tert-Butyl peroxybenzoate; trimethylsilylazide In acetonitrile at 50℃; for 6h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; Green chemistry; | 75% |
exemestane
A
6α-methylandrost-4-ene-3,17-dione
C
6β-methylandrost-4-ene-3,17-dione
Conditions | Yield |
---|---|
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 5%-palladium/activated carbon In ethanol for 18h; Reflux; stereoselective reaction; | A n/a B 62% C n/a |
Conditions | Yield |
---|---|
With N,N-dimethylammonium chloride In ethanol at 78℃; for 3h; Temperature; Mannich Aminomethylation; | 54.1% |
4-Fluorobenzenesulfonyl chloride
exemestane
Conditions | Yield |
---|---|
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); tris-(trimethylsilyl)silane In acetonitrile at 20℃; for 16h; Irradiation; diastereoselective reaction; | 50% |
exemestane
B
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate; acetic acid; trifluoroacetic acid In dichloromethane; acetonitrile at 20℃; for 11h; Inert atmosphere; | A 11.3 mg B 39% |
Conditions | Yield |
---|---|
With cobalt(II) tetrafluoroborate hexahydrate; N-isopropyl-N,2-dimethylpropan-2-amine In water; N,N-dimethyl-formamide; acetonitrile at 65℃; for 24h; Sealed tube; | A 30% B 33% |
Conditions | Yield |
---|---|
With cobalt(II) tetrafluoroborate hexahydrate; N-isopropyl-N,2-dimethylpropan-2-amine In N,N-dimethyl-formamide; acetonitrile at 65℃; for 24h; | A 30% B 33% |
nitromethane
exemestane
6α-(2-Nitroethyl)androsta-1,4-dien-3,17-dion
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 22h; Michael addition; Heating; | 32% |
exemestane
Conditions | Yield |
---|---|
With formic acid; dihydrogen peroxide In dichloromethane at 20℃; for 96h; | A 21% B 76.1 mg |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 20℃; for 24h; Inert atmosphere; | 13% |
exemestane
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium hydroxide In methanol; water at 0 - 20℃; for 24.5h; | 11% |
exemestane
diethyl malonate
Conditions | Yield |
---|---|
With sodium In ethanol for 7h; Michael addition; Heating; | 6% |
exemestane
6α-(2-Oxoethyl)androsta-1,4-dien-3,17-dion
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 32 percent / NaOEt / ethanol / 22 h / Heating 2.1: KOH / methanol / 3 h / 20 °C 2.2: 31 percent / aq. H2SO4 / methanol / 4 h / cooling View Scheme |
exemestane
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 32 percent / NaOEt / ethanol / 22 h / Heating 2.1: KOH / methanol / 3 h / 20 °C 2.2: 31 percent / aq. H2SO4 / methanol / 4 h / cooling 3.1: 58 percent / acetic acid / 22 h / 20 - 60 °C 4.1: 87 percent / CAN / acetone; H2O / 0.5 h View Scheme |
exemestane
Dimethyl-4-[(3,17-dioxoandrosta-1,4-dien-6α-yl)methyl]-2,6-dimethyl-1,4-dihydro-3,5-pyridindicarboxylat
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 32 percent / NaOEt / ethanol / 22 h / Heating 2.1: KOH / methanol / 3 h / 20 °C 2.2: 31 percent / aq. H2SO4 / methanol / 4 h / cooling 3.1: 58 percent / acetic acid / 22 h / 20 - 60 °C View Scheme |
exemestane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature 2: 38 percent / 20percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
exemestane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature 2: 42 percent / 20percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
The Exemestane, with the CAS registry number 107868-30-4, is also known as 6-Methylenandrosta-1,4-diene-3,17-dione; 10,13-Dimethyl-6-methylidene-7,8,9,10,11,12,13,14,15,16-decahydrocyclopenta[a]phenanthrene-. It belongs to the product categories of Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Pfizer compounds;Steroid and Hormone.This chemical's molecular formula is C20H24O2 and molecular weight is 296.40. What's more,Its systematic name is 6-Methyleneandrosta-1,4-diene-3,17-dione.It is a white to light yellow crystal powder.Exemestane is used as an antineoplastic.An oral steroidal aromatase inhibitor used in the adjuvant treatment of hormonally-responsive breast cancer in postmenopausal women.
Physical properties about Exemestane are:
(1)ACD/LogP: 2.432; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.43; (4)ACD/LogD (pH 7.4): 2.43; (5)ACD/BCF (pH 5.5): 41.52; (6)ACD/BCF (pH 7.4): 41.52; (7)ACD/KOC (pH 5.5): 501.13; (8)ACD/KOC (pH 7.4): 501.13; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.572; (13)Molar Refractivity: 85.797 cm3; (14)Molar Volume: 260.59 cm3; (15)Surface Tension: 42.9010009765625 dyne/cm; (16)Density: 1.137 g/cm3; (17)Flash Point: 168.985 °C; (18)Enthalpy of Vaporization: 71.317 kJ/mol; (19)Boiling Point: 453.719 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.
Preparation of Exemestane:
Triethyl orthoformate and ethanol are dissolved in tetrahydrofuran.In the presence of p-toluenesulfonic acid reaction,add N-methyl aniline and formaldehyde solution to continue to respond. The Mannich reaction products are soluble in benzoic acid and anhydrous 2 chew alkyl.Under the action of the DDQ,exemestane can be received, with a total yield of 45%.
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