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107868-30-4

Basic Information
CAS No.: 107868-30-4
Name: 6-Methyleneandrosta-1,4-diene-3,17-dione
Article Data: 19
Cas Database
Molecular Structure:
Molecular Structure of 107868-30-4 (6-Methyleneandrosta-1,4-diene-3,17-dione)
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
Solubility: N/A
Appearance: white to light yellow crystal powder
Hazard Symbols: T,N
Risk Codes: 60-61-51
Safety: 53-22-36/37-57
Transport Information: N/A
PSA: 34.14000
LogP: 4.02950
Synthetic route
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

107868-30-4

exemestane

Conditions
ConditionsYield
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;
933455-74-4

6α-hydroxymethylandrosta-1,4-diene-3,17-dione

107868-30-4

exemestane

Conditions
ConditionsYield
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%

17-hydroxyimino-6-methylenandrosta-1,4-diene-3-one

107868-30-4

exemestane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water; acetone at 25 - 30℃; for 10h; Solvent; Reagent/catalyst; Temperature; Jones Oxidation; Inert atmosphere;88.2%
19457-55-7

6-methylene-androst-4-ene 3,17-dione

107868-30-4

exemestane

Conditions
ConditionsYield
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%
67-56-1

methanol

121021-51-0

6β-hydroxymethylandrosta-1,4-diene-3,17-dione

A

(6S,8R,9S,10R,13S,14S)-6-(methoxymethyl)-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione

B

107868-30-4

exemestane

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 24h;A 8%
B 60%
19457-55-7, 51154-17-7

6-Methylen-4-androsten-3,17-dion

107868-30-4

exemestane

Conditions
ConditionsYield
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%
897-06-3

Androsta-1,4-diene-3,17-dione

107868-30-4

exemestane

Conditions
ConditionsYield
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
67737-88-6

1α,3-dipyrrolidinylandrosta-3,5-dien-17-one

107868-30-4

exemestane

Conditions
ConditionsYield
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
846-48-0

1-dehydrotestosterone

107868-30-4

exemestane

Conditions
ConditionsYield
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
861395-77-9

C21H28O5S

107868-30-4

exemestane

Conditions
ConditionsYield
With potassium hydroxide In methanol; dichloromethane; water at 25℃; Heating / reflux;
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    Exemestane CAS No.:107868-30-4 Name: Exemestane Synonyms: 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- Molecular Structure Mole

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Specification

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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