4,16-Androstadien-3-one supplier

Name
4,16-Androstadien-3-one
EINECS
CAS No. 4075-07-4
Article Data24
CAS DataBase
Density 1.07 g/cm³
Solubility
Melting Point 131.5-133.5 °C
Formula C₁₉H₂₆O
Boiling Point 390.3 °C at 760mmHg
Molecular Weight 270.415
Flash Point 179.2 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4,16-Androstadien-3-one;Androstadienone;NSC 93234;D4,16-Androstadien-3-one;
PSA 17.07000
LogP 4.68440

Synthetic route

: 19865-18-0
17β-methoxycarbonyloxy-androst-4-en-3-one

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
In toluene at 460℃;	90%
In acetone; toluene	90%

: 3396-11-0
cesium acetate

: 182243-71-6
Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

A: 4075-07-4
4,16-androstadien-3-one

B: 1425-09-8
3-oxoandrost-4-en-17α-yl acetate

Conditions

Conditions	Yield
With 18-crown-6 ether In benzene for 72h; Heating;	A 10% B 76%

...Expand

: 182243-71-6
Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

A: 4075-07-4
4,16-androstadien-3-one

B: 1425-09-8
3-oxoandrost-4-en-17α-yl acetate

Conditions

Conditions	Yield
With 18-crown-6 ether; cesium acetate In benzene for 72h; Heating;	A 10% B 76%

: 1255-57-8
17β-tosyloxyandrostan-4-en-3-one

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
Stage #1: 17β-tosyloxyandrostan-4-en-3-one With tetrabutylammonium acetate In 1-methyl-pyrrolidin-2-one at 160℃; for 4h; Stage #2: With potassium hydroxide In ethanol at 20℃; for 48h;	61%
With aluminum oxide In benzene for 20h; Heating;

: 120-72-9
indole

: 100772-35-8
17-iodoandrosta-4,16-dien-3-one

A: 17-(1H-indol-1-yl)androsta-4,16-dien-3-one

B: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
With copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione; potassium carbonate In dimethyl sulfoxide at 100℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	A 55% B 15 %Spectr.
With copper(l) iodide; potassium carbonate; butane-2,3-dione dioxime In dimethyl sulfoxide at 100℃; for 24h; Reagent/catalyst; Inert atmosphere;	A 8 %Spectr. B 72 %Spectr.

...Expand

: bis(androst-4-en-3-on)-17β-yl oxalate

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
at 600℃; under 0.00750075 Torr; for 1h; Flash vacuum pyrolysis;	29%

: 36025-82-8
3-oxoandrost-4-en-17α-yl benzoate

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
at 300℃; Erhitzen unter Stickstoff;
at 300℃;

: 1224-94-8
HAD

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
With cyclohexanone; aluminum isopropoxide; toluene

: 58-22-0
testosterone

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / pyridine; various solvent(s) / 24 h / 0 °C 2: 90 percent / toluene / 460 °C View Scheme
(i) MeSO2Cl, Py, (ii) LiCl, DMF; Multistep reaction;

: 159949-15-2
testosterone triflate

A: 17α-Azido-androst-4-en-3-on

B: 38978-06-2
17-methyl-18-norandrosta-4,13(17)-dien-3-one

C: 4075-07-4
4,16-androstadien-3-one

D: 17β-Methyl-18-norandrosta-4,13-dien-3-on

Conditions

Conditions	Yield
With lithium azide In N,N-dimethyl-formamide at 25℃; for 0.5h; Substitution;

...Expand

: 159949-15-2
testosterone triflate

A: 38978-06-2
17-methyl-18-norandrosta-4,13(17)-dien-3-one

B: 4075-07-4
4,16-androstadien-3-one

C: 17β-Methyl-18-norandrosta-4,13-dien-3-on

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 90℃; for 0.0833333h; Substitution;

...Expand

: 182243-71-6
Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

A: 17α-Azido-androst-4-en-3-on

B: 38978-06-2
17-methyl-18-norandrosta-4,13(17)-dien-3-one

C: 4075-07-4
4,16-androstadien-3-one

D: 17β-Methyl-18-norandrosta-4,13-dien-3-on

Conditions

Conditions	Yield
With lithium azide In N,N-dimethyl-formamide at 90℃; for 9h; Substitution;

...Expand

: 58-22-0
testosterone

androstene-(5)-diol-(3.17): androstene-(5)-diol-(3.17)

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 0 °C 2: LiN3 / dimethylformamide / 9 h / 90 °C View Scheme

: 58-22-0
testosterone

<2,4,6-triiodo-phenoxy>-acetyl chloride: <2,4,6-triiodo-phenoxy>-acetyl chloride

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / pyridine / 0.25 h / 0 - 20 °C 2: 10 percent / 18-crown-6 / benzene / 72 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 100 percent / pyridine / 0.25 h / 0 - 20 °C 2: 10 percent / CsOAc, 18-crow-6 / benzene / 72 h / Heating View Scheme

: 161061-98-9
Estra-5(10),16-dien-3-one

: 64-17-5
ethanol

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
In ethyl acetate

Al(OPri)3: Al(OPri)3

: 30505-67-0
5α-5,16-Androstadien-3α-ol

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
In water; cyclohexanone; toluene

: C20H27IO

A: 17-(1H-indol-1-yl)androsta-4,16-dien-3-one

B: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol; water / 2.5 h / Reflux 2: potassium carbonate; 2,2,6,6-tetramethylheptane-3,5-dione; copper(l) iodide / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

: C20H27IO

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol; water / 2.5 h / Reflux 2: potassium carbonate; indole; copper(l) iodide; N,N`-dimethylethylenediamine / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

: 1131428-48-2
3-methoxyandrosta-3,5-dien-17-one hydrazone

A: 17-(1H-indol-1-yl)androsta-4,16-dien-3-one

B: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; iodine / 1,4-dioxane / 0.5 h 2: hydrogenchloride / ethanol; water / 2.5 h / Reflux 3: potassium carbonate; 2,2,6,6-tetramethylheptane-3,5-dione; copper(l) iodide / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

: 1131428-48-2
3-methoxyandrosta-3,5-dien-17-one hydrazone

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; iodine / 1,4-dioxane / 0.5 h 2: hydrogenchloride / ethanol; water / 2.5 h / Reflux 3: potassium carbonate; indole; copper(l) iodide; N,N`-dimethylethylenediamine / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

: 57144-06-6
3-methoxyandrosta-3,5-dien-17-one

A: 17-(1H-indol-1-yl)androsta-4,16-dien-3-one

B: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate; triethylamine / ethanol / 2 h / Reflux 2: triethylamine; iodine / 1,4-dioxane / 0.5 h 3: hydrogenchloride / ethanol; water / 2.5 h / Reflux 4: potassium carbonate; 2,2,6,6-tetramethylheptane-3,5-dione; copper(l) iodide / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

: 57144-06-6
3-methoxyandrosta-3,5-dien-17-one

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate; triethylamine / ethanol / 2 h / Reflux 2: triethylamine; iodine / 1,4-dioxane / 0.5 h 3: hydrogenchloride / ethanol; water / 2.5 h / Reflux 4: potassium carbonate; indole; copper(l) iodide; N,N`-dimethylethylenediamine / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

: 100772-35-8
17-iodoandrosta-4,16-dien-3-one

: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
With indole; copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 100℃; for 24h; Reagent/catalyst; Inert atmosphere;	60 %Spectr.

: 100772-35-8
17-iodoandrosta-4,16-dien-3-one

: 693-02-7
hex-1-yne

A: 17-(hex-1-yn-1-yl)androsta-4,16-dien-3-one

B: 4075-07-4
4,16-androstadien-3-one

Conditions

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; triphenylphosphine In dimethyl sulfoxide at 100℃; Reagent/catalyst; Sonogashira Cross-Coupling; Inert atmosphere;	A 22 %Spectr. B 11 %Spectr.

...Expand

: 4075-07-4
4,16-androstadien-3-one

A: 63015-31-6
4α,5α-epoxyandrost-16-en-3-one

B: 4β,5β-epoxyandrost-16-en-3-one

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In methanol at 0℃; for 24h;	A 13% B 76%

: 4075-07-4
4,16-androstadien-3-one

: 22614-28-4
16β-hydroxyandrost-4-en-3-one

Conditions

Conditions	Yield
Stage #1: 4,16-androstadien-3-one With mercury(II) diacetate In tetrahydrofuran; water at 20℃; for 72h; Stage #2: With sodium hydroxide; sodium tetrahydroborate In tetrahydrofuran; water for 0.0333333h;	45%

: 4075-07-4
4,16-androstadien-3-one

: 63015-08-7
androsta-1,4,16-trien-3-one

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 80℃; for 15h;	43%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane

: 4075-07-4
4,16-androstadien-3-one

: 51067-43-7
Androstene oxide

Conditions

Conditions	Yield
With Perbenzoic acid; chloroform

: 4075-07-4
4,16-androstadien-3-one

: 63014-91-5
androsta-4,6,16-trien-3-one

Conditions

Conditions	Yield
With sodium hydroxide; chloranil; acetic acid In methanol; n-heptane; water; toluene; tert-butyl alcohol; benzene
With chloranil; acetic acid In tert-butyl alcohol

: 4075-07-4
4,16-androstadien-3-one

: 122-51-0
orthoformic acid triethyl ester

: 63015-17-8
3-ethoxy-androsta-3,5,16-triene

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane

: 4075-07-4
4,16-androstadien-3-one

: 2872-90-4
4-androsten-3-one

Conditions

Conditions	Yield
With hydrogen; Wilkinson's catalyst In ethanol for 4h; Ambient temperature;	1.0 g

: 4075-07-4
4,16-androstadien-3-one

A: androsta-4,16-dien-3α-ol

B: androsta-4,16-dien-3β-ol

Conditions

Conditions	Yield
With ethanol; water; lithium tri-sec-butyl(hydrido)borate 1.) THF, r.t., 3 h; 2.) -55 deg C; Yield given. Multistep reaction. Yields of byproduct given;

: 4075-07-4
4,16-androstadien-3-one

: 406919-61-7
16β-trichloroacetoxyandrost-4-en-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: mercuric acetate / H2O; tetrahydrofuran / 72 h / 20 °C 1.2: 45 percent / 3.0 M NaOH; NaBH4 / H2O; tetrahydrofuran / 0.03 h 2.1: 83 percent / Et3N; N,N-dimethylaminopyridine / CH2Cl2 / 2.5 h / 0 - 20 °C View Scheme

: 4075-07-4
4,16-androstadien-3-one

: 20311-30-2
5α-androstan-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.0 g / hydrogen / chloro-tris(triphenylphosphine)rhodium / ethanol / 4 h / Ambient temperature 2: 1.) 1,2-ethanedithiol, boron trifluoride etherate; 2.) methanol / 2.) Raney-Ni / 1.) acetic acid, r.t., 2 d; 2.) 20 h 3: 1.) m-chloroperbenzoic acid; 2.) lithium aluminium hydride / 1.) CHCl3, r.t., 1 h; 2.) dioxane, reflux, 4 h View Scheme

: 4075-07-4
4,16-androstadien-3-one

: 38544-66-0
3H-androst-4-ene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.0 g / hydrogen / chloro-tris(triphenylphosphine)rhodium / ethanol / 4 h / Ambient temperature 2: 1.) 1,2-ethanedithiol, boron trifluoride etherate; 2.) methanol / 2.) Raney-Ni / 1.) acetic acid, r.t., 2 d; 2.) 20 h View Scheme

: 4075-07-4
4,16-androstadien-3-one

: 5β-androstan-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.0 g / hydrogen / chloro-tris(triphenylphosphine)rhodium / ethanol / 4 h / Ambient temperature 2: 1.) 1,2-ethanedithiol, boron trifluoride etherate; 2.) methanol / 2.) Raney-Ni / 1.) acetic acid, r.t., 2 d; 2.) 20 h 3: 1.) m-chloroperbenzoic acid; 2.) lithium aluminium hydride / 1.) CHCl3, r.t., 1 h; 2.) dioxane, reflux, 4 h View Scheme

: 4075-07-4
4,16-androstadien-3-one

: androsta-1,4,6,16-tetraen-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / 1,4-dioxane 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane View Scheme

: 4075-07-4
4,16-androstadien-3-one

: 6β-Iodandrosta-4,16-dien-3-on

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / 1,4-dioxane 2: (i) N-iodo-succinimide, (ii) (hydrolysis) View Scheme

: 4075-07-4
4,16-androstadien-3-one

: 63015-22-5
3-ethoxy-6-chloro-androsta-3,5,16-triene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / 1,4-dioxane 2: (i) N-chloro-succinimide, acetone, H2O, (ii) (hydrolysis) 3: toluene-4-sulfonic acid View Scheme

4,16-Androstadien-3-one Specification

The IUPAC name of 4,16-Androstadien-3-one is (8S,9S,10R,13R,14S)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one. With the CAS registry number 4075-07-4, it is also named as Androsta-4,16-dien-3-one (8CI)(9CI). It has strong pheromone-like activities in humans. And it is a metabolite of the sex hormone testosterone. However, this chemical does not exhibit any known androgenic or anabolic effects.

The other characteristics of 4,16-Androstadien-3-one can be summarized as: (1)ACD/LogP: 5.03; (2)# of Rule of 5 Violations: 1; (3)#H bond acceptors: 1; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 0; (6)Polar Surface Area: 17.07 Å²; (7)Index of Refraction: 1.559; (8)Molar Refractivity: 81.51 cm³; (9)Molar Volume: 252.2 cm³; (10)Polarizability: 32.31×10^-24 cm³; (11)Surface Tension: 40.4 dyne/cm; (12)Flash Point: 179.2 °C; (13)Enthalpy of Vaporization: 63.97 kJ/mol; (14)Boiling Point: 390.3 °C at 760 mmHg; (15)Vapour Pressure: 2.69E-06 mmHg at 25°C; (16)Tautomer Count: 5; (17)Exact Mass: 270.198365; (18)MonoIsotopic Mass: 270.198365; (19)Topological Polar Surface Area: 17.1; (20)Heavy Atom Count: 20; (21)Complexity: 514; (22)Defined Atom StereoCenter Count: 5.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C4\C=C3/C(C)(C2CCC1(/C=C\CC1C2CC3)C)CC4
2. InChI:InChI=1/C19H26O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,12,15-17H,4-8,10-11H2,1-2H3
3. InChIKey:HNDHDMOSWUAEAW-UHFFFAOYAK

Product Name

4,16-Androstadien-3-one

Synthetic route

4,16-Androstadien-3-one Specification

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