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| CAS No.: | 107868-30-4 |
|---|---|
| Name: | Exemestane |
| Molecular Structure: | |
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| Formula: | C20H24O2 |
| Molecular Weight: | 296.409 |
| Synonyms: | Exemestane [USAN:INN:BAN];Aromasil;Aromasin;FCE 24304;Exemestane Tablets;Androsta-1,4-diene-3,17-dione, 6-methylene-;Exemestano;Exemestano [INN-Spanish];Exemestanum;Exemestanum [INN-Latin];HSDB 7463;Exemestane; |
| EINECS: | 643-090-2 |
| Density: | 1.13 g/cm3 |
| Melting Point: | 155.13 ºC |
| Boiling Point: | 453.7 ºC at 760 mmHg |
| Flash Point: | 169 ºC |
| Appearance: | white to light yellow crystal powder |
| Hazard Symbols: | T,N |
| Risk Codes: | 60-61-51 |
| Safety: | 53-22-36/37-57 |
| PSA: | 34.14000 |
| LogP: | 4.02950 |
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; |
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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%.
