3-Methoxyandrosta-3,5-dien-17-one

Base Information

• Chemical Name: 3-Methoxyandrosta-3,5-dien-17-one
• CAS No.: 57144-06-6
• Molecular Formula: C20H28 O2
• Molecular Weight: 300.441
• European Community (EC) Number: 260-591-8
• UNII: EO7QDL04JK
• DSSTox Substance ID: DTXSID00205775
• Nikkaji Number: J349.100E
• Wikidata: Q76005579
• Mol file: 57144-06-6.mol

Synonyms:3-Methoxyandrosta-3,5-dien-17-one;57144-06-6;EO7QDL04JK;(8R,9S,10R,13S,14S)-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-one;Androstenedione Methylenolether;EINECS 260-591-8;EC 260-591-8;3-Methoxyandrosta-3,5-dien-17-one (Androstenedione Methylenolether);UNII-EO7QDL04JK;SCHEMBL5310190;DTXSID00205775;3-methoxy-3,5-androstadien-17-one;3-Methoxyandrosta-3,5-diene-17-one;AKOS030240720;TESTOSTERONE IMPURITY J [EP IMPURITY];(3aS,3bR,9aR,9bS,11aS)-7-methoxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-one

Chemical Property of 3-Methoxyandrosta-3,5-dien-17-one

Chemical Property:

• Vapor Pressure: 3.63E-08mmHg at 25°C
• Boiling Point: 446.5°Cat760mmHg
• Flash Point: 187.9°C
• PSA: 26.30000
• Density: 1.09g/cm³
• LogP: 4.65850
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 300.208930132
• Heavy Atom Count: 22
• Complexity: 572

Purity/Quality:

99.9% ^*data from raw suppliers

3-METHOXY ANDROSTA-3,5-DIEN-17-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CC=C4C3(CCC(=C4)OC)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CCC(=C4)OC)C
• Uses: 3-methoxyandrosta-3,5-dien-17-one is an intermediate used in the synthesis of Drospirenone (D689500) from Androstenedione (A637550).

Technology Process of 3-Methoxyandrosta-3,5-dien-17-one

There total 6 articles about 3-Methoxyandrosta-3,5-dien-17-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

Androstenedione (63-05-8) + trimethyl orthoformate (149-73-5) → 3-methoxyandrosta-3,5-dien-17-one (57144-06-6)

Guidance literature:

With p-toluenesulfonic acid hydrochloride; In methanol; at 35 - 45 ℃; for 5.25h; Inert atmosphere;

Reference yield: 94.27%

Androstenedione (63-05-8) + orthoformic acid triethyl ester (122-51-0) → 3-methoxyandrosta-3,5-dien-17-one (57144-06-6)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; chloroform; at 38 ℃; for 2h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

Reference yield: 94.0%

Trimethyl orthoacetate (1445-45-0) + Androstenedione (63-05-8) → 3-methoxyandrosta-3,5-dien-17-one (57144-06-6)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; methanol; at 30 ℃; for 4h; Inert atmosphere; Industrial scale;

upstream raw materials:

Androstenedione

trimethyl orthoformate

orthoformic acid triethyl ester

Trimethyl orthoacetate

Downstream raw materials:

testosterone heptanoate

testosterone propionate

17-(1H-imidazol-1-yl)androsta-4,16-dien-3-one

4,16-androstadien-3-one

Refernces

• 1、 -. "Method for synthesizing methyl 3-oxo-4-androstene-17beta-carboxylate". Paragraph 0013; 0030; 0031; 0032; 0039; 0040; 0041. . Retrieved 2019/03/29.
• 2、 -. "The invention relates to a raw material synthetic stone androstenedione cholic acid (by machine translation)". Paragraph 0017; 0018. . Retrieved 2019/01/08.