17-Acetyl-10,13-dimethyl-6,7,8,12,14,15-hexahydrocyclopenta[a]phenanthren-3-one

Base Information

• Chemical Name: 17-Acetyl-10,13-dimethyl-6,7,8,12,14,15-hexahydrocyclopenta[a]phenanthren-3-one
• CAS No.: 117048-56-3
• Molecular Formula: C21H24O2
• Molecular Weight: 308.42
• European Community (EC) Number: 690-795-6
• Mol file: 117048-56-3.mol

Synonyms:Pregna-1,4,9(11),16-tetraene-3,20-dione;117048-56-3

Chemical Property of 17-Acetyl-10,13-dimethyl-6,7,8,12,14,15-hexahydrocyclopenta[a]phenanthren-3-one

Chemical Property:

• Vapor Pressure: 1.38E-09mmHg at 25°C
• Melting Point: 195-198°C
• Refractive Index: 1.59
• Boiling Point: 485.7 °C at 760 mmHg
• Flash Point: 180 °C
• PSA: 34.14000
• Density: 1.15 g/cm³
• LogP: 4.33970
• Storage Temp.: Refrigerator
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 308.177630004
• Heavy Atom Count: 23
• Complexity: 733

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CCC2C1(CC=C3C2CCC4=CC(=O)C=CC43C)C
• Uses: Intermediate in the preparation of Methasone derivatives.

Technology Process of 17-Acetyl-10,13-dimethyl-6,7,8,12,14,15-hexahydrocyclopenta[a]phenanthren-3-one

There total 1 articles about 17-Acetyl-10,13-dimethyl-6,7,8,12,14,15-hexahydrocyclopenta[a]phenanthren-3-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:

3'-methylspiro[pregna-1,4-dien-3,2'(3'H)benzothiazol]-9(11),16-dien-20-one + ethyl vinyl ether (109-92-2,25104-37-4) → 2-(1-ethoxyethylthio)-N-methylbenzeneamine + 17-acetyl-10,13-dimethyl-6,7,8,10,12,13,14,15-octahydrocyclopenta[a]phenathren-3 (117048-56-3)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.steroids.2006.10.008

Reference yield:

17-acetyl-10,13-dimethyl-6,7,8,10,12,13,14,15-octahydrocyclopenta[a]phenathren-3 (117048-56-3) → triamcinolone acetonide (76-25-5,911437-91-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydroxide / methanol / -5 - 5 °C

1.2: 5 - 20 °C / Darkness

2.1: potassium permanganate; formic acid / acetone / -5 - 5 °C

3.1: toluene-4-sulfonic acid / dichloromethane / 20 °C

4.1: perchloric acid / -5 - 5 °C

5.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / acetone / -5 - 5 °C

6.1: hydrogen fluoride / chloroform / -40 °C

With potassium permanganate; formic acid; perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; hydrogen fluoride; toluene-4-sulfonic acid; sodium hydroxide; In methanol; dichloromethane; chloroform; acetone;

Reference yield:

17-acetyl-10,13-dimethyl-6,7,8,10,12,13,14,15-octahydrocyclopenta[a]phenathren-3 (117048-56-3) → triamcinolone (124-94-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydroxide / methanol / Darkness; Cooling with ice

1.2: 20 °C

2.1: potassium permanganate; formic acid / acetone / -5 - 5 °C

3.1: triethylamine; dmap / chloroform

4.1: 5,5-dibromohydantoin; perchloric acid / acetone / -5 - 5 °C

5.1: hydrogen fluoride / chloroform; water / -40 °C

5.2: 40 °C

With dmap; potassium permanganate; formic acid; perchloric acid; 5,5-dibromohydantoin; hydrogen fluoride; triethylamine; sodium hydroxide; In methanol; chloroform; water; acetone;

upstream raw materials:

ethyl vinyl ether

Downstream raw materials:

triamcinolone

C₂₄H₃₀O₆

triamcinolone acetonide

Refernces