Methyl 3-oxo-4-androstene-17beta-carboxylate supplier

Name
Methyl 3-oxo-4-androstene-17beta-carboxylate
EINECS
CAS No. 2681-55-2
Article Data27
CAS DataBase
Density 1.12 g/cm³
Solubility
Melting Point 130-131 °C
Formula C₂₁H₃₀O₃
Boiling Point 441.8 °C at 760 mmHg
Molecular Weight 330.467
Flash Point 191.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Androst-4-ene-17b-carboxylic acid, 3-oxo-, methylester (7CI,8CI);4-Androsten-3-one 17b-carboxylic acid methyl ester;L 589.170;Methyl 4-androsten-3-one 17b-carboxylate;Org 7329-0;
PSA 43.37000
LogP 4.30750

Synthetic route

: 6247-91-2
17β-androstane-4-ene-3-keto-17-formaldehyde

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; potassium iodide In methanol at 20℃; for 6.5h; Reagent/catalyst; Reflux;	93%

: 302-97-6
androst-4-en-3-one-17β-carboxylic acid

: 85622-93-1
temozolomide

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 60℃; for 4h; Sealed tube;	89%

: 85541-82-8, 95119-09-8, 7254-03-7
methyl 5-androsten-3β-ol-17β-carboxylate

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With cyclohexanone; aluminum isopropoxide In toluene	87%
With aluminum isopropoxide In cyclohexanone; toluene at 110℃; for 3h; Oppenauer Oxidation; Inert atmosphere;	82%
With aluminum isopropoxide In cyclohexanone; toluene for 4h; Oxidation; Oppennauer oxidation; Heating;	70.62%

: 1634-04-4
tert-butyl methyl ether

: 302-97-6
androst-4-en-3-one-17β-carboxylic acid

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With iron(III) trifluoromethanesulfonate at 90℃; Schlenk technique;	79%

: 67-56-1
methanol

: C24H31NO2

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In toluene at 20℃; for 18h; Sealed tube; chemoselective reaction;	64%

: 67-56-1
methanol

: 121329-22-4
17-Acetoxy-21-(acetylthio)-4-pregnen-3,20-dion

A: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B: 121329-29-1
(17R)-4-Androsten-17-spiro-3'-(1',2'-dithiolan)-3,4'-dion

Conditions

Conditions	Yield
With sodium azide for 22h; Ambient temperature;	A 48% B 10%

...Expand

: 121329-22-4
17-Acetoxy-21-(acetylthio)-4-pregnen-3,20-dion

A: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B: 121329-29-1
(17R)-4-Androsten-17-spiro-3'-(1',2'-dithiolan)-3,4'-dion

Conditions

Conditions	Yield
With sodium azide In methanol at 50℃; for 1.5h;	A 8% B 39%

: 186581-53-3, 908094-01-9
diazomethane

: 302-97-6
androst-4-en-3-one-17β-carboxylic acid

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With diethyl ether

: 111497-46-2
methyl 3-oxo-androst-1,4-diene-17β-carboxylate

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Hydrogenation;

: 114127-58-1
2β,4β-dibromo-3-oxo-5β-androstane-17β-carboxylic acid methyl ester

A: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B: 111407-58-0
3-oxo-5β-androst-1-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With acetone; sodium iodide Erwaermen des Reaktionsprodukts mit Zink-Pulver und Aethanol;

: 85541-82-8, 95119-09-8, 7254-03-7
methyl 5-androsten-3β-ol-17β-carboxylate

: 108-94-1
cyclohexanone

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With aluminum isopropoxide; toluene

: 85541-82-8, 95119-09-8, 7254-03-7
methyl 5-androsten-3β-ol-17β-carboxylate

: 108-94-1
cyclohexanone

: 555-31-7
aluminum isopropoxide

: 108-88-3
toluene

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

...Expand

: 114127-58-1
2β,4β-dibromo-3-oxo-5β-androstane-17β-carboxylic acid methyl ester

A: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B 3-oxo-androst-1-ene-17β-carboxylic acid methyl ester: 3-oxo-androst-1-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With acetone; sodium iodide Erwaermen des Reaktionsprodukts mit Zink-Pulver und Aethanol;

: 55955-57-2
3β,5-dihydroxy-21-nor-5β-pregnanoic acid-(20)-methyl ester

: 64-19-7
acetic acid

chromium (VI)-oxide: chromium (VI)-oxide

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Erhitzen des Reaktionsprodukts mit Essigsaeure;

...Expand

: 17β-acetoxy-3β-hydroxy-3α-methylandrost-4-ene

A: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B: 17β-acetoxy-3β,4β-epoxy-5β-hydroxy-3α-methylandrostane

Conditions

Conditions	Yield
With chromium(VI) oxide In acetone at 20℃;	A 50 mg B 290 mg

: 15173-68-9, 10325-79-8
etienic acid

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: cesium fluoride / dimethylformamide / 24 h / 20 °C 2: 3.1 g / cyclohexanone; aluminium isopropoxide / toluene / Heating View Scheme
Multi-step reaction with 2 steps 1: 82 percent / p-toluenesulfonic acid / 5 h / Heating 2: 87 percent / Al(i-PrO)3, cyclohexanone / toluene View Scheme
Multi-step reaction with 2 steps 1: Reaktion ueber mehrere Stufen 2: diethyl ether View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / Reflux 2: aluminum isopropoxide / toluene; cyclohexanone / 3 h / 110 °C / Inert atmosphere View Scheme

: 145-13-1
Pregnenolone

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: I2 / 1.5 h / Heating 2: methanol / 1 h / Heating 3: 70.62 percent / Al(i-PrO)3 / cyclohexanone; toluene / 4 h / Heating View Scheme
Multi-step reaction with 3 steps 1: I2 / 1 h / Heating 2: methanol / 1 h / Heating 3: 1.) Al(i-PrO)3, 2.) Supercel, Darco KB / 1.) toluene, cyclohexanone, reflux, 1 h, 2.) toluene, cyclohexanone, water, 15 min View Scheme
Multi-step reaction with 3 steps 1: iodine / 1.5 h / 90 °C / Inert atmosphere; Reflux 2: sodium methylate / 16 h / Inert atmosphere; Reflux 3: cyclohexanone; aluminum isopropoxide / toluene / 4 h / Reflux; Inert atmosphere View Scheme

: 73672-02-3
pregnenolone 21-pyridinium iodide

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: 70.62 percent / Al(i-PrO)3 / cyclohexanone; toluene / 4 h / Heating View Scheme
Multi-step reaction with 2 steps 1: methanol / 1 h / Heating 2: 1.) Al(i-PrO)3, 2.) Supercel, Darco KB / 1.) toluene, cyclohexanone, reflux, 1 h, 2.) toluene, cyclohexanone, water, 15 min View Scheme
Multi-step reaction with 2 steps 1: sodium methylate / 16 h / Inert atmosphere; Reflux 2: cyclohexanone; aluminum isopropoxide / toluene / 4 h / Reflux; Inert atmosphere View Scheme

: 1778-02-5
Pregnenolone acetate

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaOBr, 2.) HCl / 1.) dioxane, water 2: 82 percent / p-toluenesulfonic acid / 5 h / Heating 3: 87 percent / Al(i-PrO)3, cyclohexanone / toluene View Scheme
Multi-step reaction with 3 steps 1.1: sodium hypobromide / water; 1,4-dioxane / 3 h / 5 - 8 °C 1.2: 0.25 h / Reflux 1.3: 24 h / 5 - 90 °C 2.1: sulfuric acid / 3 h / Reflux 3.1: aluminum isopropoxide / toluene; cyclohexanone / 3 h / 110 °C / Inert atmosphere View Scheme

: 64-85-7
21-Hydroxyprogesterone

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 68.3 percent / H2O2, 0.2N NaOH / hemin / methanol / 4 h / 20 °C View Scheme

: 113926-62-8
21-(Acetylthio)-17-hydroxy-4-pregnen-3,20-dion

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / DMAP / bis-(2-methoxy-ethyl) ether / 17 h / Ambient temperature 2: 48 percent / NaN3 / 22 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 73 percent / DMAP / bis-(2-methoxy-ethyl) ether / 17 h / Ambient temperature 2: 8 percent / NaN3 / methanol / 1.5 h / 50 °C View Scheme

: 50305-74-3
methyl 3-oxo-5β-androstane-17β-carboxylate

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine 2: NaI; acetone / Erwaermen des Reaktionsprodukts mit Zink-Pulver und Aethanol View Scheme
Multi-step reaction with 2 steps 1: bromine 2: NaI; acetone / Erwaermen des Reaktionsprodukts mit Zink-Pulver und Aethanol View Scheme

: 85541-82-8, 95119-09-8, 7254-03-7
methyl 5-androsten-3β-ol-17β-carboxylate

A: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

B: 116934-48-6
methyl 3-oxo-androst-4,6-diene-17β-carboxylate

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 0 - 20℃; Overall yield = 75 %;

: 63-05-8
Androstenedione

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / tetrahydrofuran / 5 h / 5 °C / Inert atmosphere 2: n-butyllithium / 2-methyltetrahydrofuran / 6 h / -60 - -45 °C / Inert atmosphere 3: tert.-butylhydroperoxide; potassium iodide / methanol / 6.5 h / 20 °C / Reflux View Scheme

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 302-97-6
androst-4-en-3-one-17β-carboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In methanol for 5h; Hydrolysis; Heating;	100%
With potassium hydroxide In ethanol; water	95%
With potassium hydroxide In methanol; water for 3h; Inert atmosphere; Reflux;	89%

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 119169-85-6
Methyl 3-bromoandrosta-3,5-diene-17β-carboxylate

Conditions

Conditions	Yield
With phosphorus tribromide In acetic acid for 21h; Ambient temperature;	85%

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 150723-49-2
3β-hydroxy-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With diisopropoxytitanium(III) tetrahydroborate In dichloromethane at -20℃; for 0.5h;	82%
With sodium tetrahydroborate
With sodium tetrahydroborate In methanol at 0℃; Reduction;

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 111497-46-2
methyl 3-oxo-androst-1,4-diene-17β-carboxylate

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 48h; Reflux;	81.2%

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 116934-48-6
methyl 3-oxo-androst-4,6-diene-17β-carboxylate

Conditions

Conditions	Yield
With chloranil In chloroform; tert-butyl alcohol	70%

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 74-88-4
methyl iodide

: 1609387-14-5
C23H34O3

Conditions

Conditions	Yield
Stage #1: 3-oxo-androst-4-ene-17β-carboxylic acid methyl ester With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;	63%

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

A: 23737-99-7
androsta-3,5-diene-17β-carboxylic acid methyl ester

B: 150723-49-2
3β-hydroxy-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium tetrahydroborate

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 423166-44-3
2ξ,6ξ-dibromo-3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With bromine

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

A: 10002-85-4
methyl 3β-hydroxy-5α-androstane-17β-carboxylate

B: 74464-95-2
3α-hydroxy-5β-androstan-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With methanol; palladium anschliessend Hydrierung an Platin in Methanol und Essigsaeure; Isolierung von Digitonin;
With methanol; palladium anschliessend Hydrierung an Platin in Methanol und Essigsaeure;

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 74497-93-1
3α-acetoxy-5β-androstane-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
With ethanol; alkaline solution; nickel Hydrogenation.Behandlung der neutralen Anteile des Reaktionsprodukts mit Acetanhydrid und Pyridin;

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 92472-33-8
17β-methoxycarbonyl-5-oxo-3,5-seco-A-nor-androstan-3-oic acid

Conditions

Conditions	Yield
With chloroform; ozone Behandeln des Reaktionsprodukts mit wss. Essigsaeure und anschliessendes Erwaermen mit Zink;
With potassium permanganate; sodium periodate; sodium carbonate In water; tert-butyl alcohol Heating;

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 108-24-7
acetic anhydride

: 75-36-5
acetyl chloride

: 911663-11-1
3-acetoxy-androstadiene-(3.5)-carboxylic acid-(17β)-methyl ester

Conditions

Conditions	Yield
at 100 - 140℃;

...Expand

: 107-31-3
Methyl formate

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 138091-50-6
(8S,9S,10R,13S,14S,17S)-2-[1-Hydroxy-meth-(Z)-ylidene]-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium methylate

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 6247-91-2
17β-androstane-4-ene-3-keto-17-formaldehyde

Conditions

Conditions	Yield
With lithium aluminium tetrahydride 1.) THF, room temperature, 1 h, 0 deg C; 2.) oxidation; Yield given. Multistep reaction;

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

: 119169-67-4
17β-carbomethoxyandrost-4-ene

Conditions

Conditions	Yield
With sodium tetrahydroborate; acetic acid; trifluoroacetic acid In dichloromethane; acetonitrile at 20℃; for 2h; Reduction;

: 67-56-1
methanol

: 2681-55-2
3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

palladium: palladium

A: 10002-85-4
methyl 3β-hydroxy-5α-androstane-17β-carboxylate

B: 74464-95-2
3α-hydroxy-5β-androstan-17β-carboxylic acid methyl ester

Conditions

Conditions	Yield
anschliessend Hydrierung an Platin in Essigsaeure enthaltendem Methanol;

...Expand

Methyl 3-oxo-4-androstene-17beta-carboxylate Specification

The CAS register number of Methyl 3-oxo-4-androstene-17beta-carboxylate is 2681-55-2. It also can be called as Androst-4-ene-17-carboxylicacid, 3-oxo-, methyl ester, (17b)- and the IUPAC name about this chemical is methyl(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxylate. The molecular formula about this chemical is C₂₁H₃₀O₃and the molecular weight is 330.46.

Physical properties about Methyl 3-oxo-4-androstene-17beta-carboxylate are: (1)ACD/LogP: 4.37; (2)ACD/LogD (pH 5.5): 4.37; (3)ACD/LogD (pH 7.4): 4.37; (4)ACD/BCF (pH 5.5): 1235.98; (5)ACD/BCF (pH 7.4): 1235.98; (6)ACD/KOC (pH 5.5): 5686.7; (7)ACD/KOC (pH 7.4): 5686.7; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 43.37Å²; (11)Index of Refraction: 1.54; (12)Molar Refractivity: 92.69 cm³; (13)Molar Volume: 295 cm³; (14)Polarizability: 36.74x10^-24cm³; (15)Surface Tension: 42.2 dyne/cm; (16)Enthalpy of Vaporization: 69.92 kJ/mol; (17)Boiling Point: 441.8 °C at 760 mmHg; (18)Vapour Pressure: 5.28E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@H](C(=O)OC)CC[C@H]3[C@@H]1CC2)C)(C)CC4
(2)InChI: InChI=1/C21H30O3/c1-20-10-8-14(22)12-13(20)4-5-15-16-6-7-18(19(23)24-3)21(16,2)11-9-17(15)20/h12,15-18H,4-11H2,1-3H3/t15-,16-,17-,18+,20-,21-/m0/s1
(3)InChIKey: XWFWMYFLNHTEBF-YFWFAHHUBB
(4)Std. InChI: InChI=1S/C21H30O3/c1-20-10-8-14(22)12-13(20)4-5-15-16-6-7-18(19(23)24-3)21(16,2)11-9-17(15)20/h12,15-18H,4-11H2,1-3H3/t15-,16-,17-,18+,20-,21-/m0/s1
(5)Std. InChIKey: XWFWMYFLNHTEBF-YFWFAHHUSA-N

Product Name

Methyl 3-oxo-4-androstene-17beta-carboxylate

Synthetic route

Methyl 3-oxo-4-androstene-17beta-carboxylate Specification

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