17-Hydroxy-19-norpregn-4-ene-3,20-dione 17-acetate

Base Information

• Chemical Name: 17-Hydroxy-19-norpregn-4-ene-3,20-dione 17-acetate
• CAS No.: 31981-44-9
• Molecular Formula: C22H30O4
• Molecular Weight: 358.478
• European Community (EC) Number: 250-882-8
• UNII: D9R4KSN7NA
• DSSTox Substance ID: DTXSID90953874
• Nikkaji Number: J145.870A
• Wikipedia: Gestonorone_acetate
• Wikidata: Q60291352
• Mol file: 31981-44-9.mol

Synonyms:31981-44-9;Gestonoronacetat;17-Hydroxy-19-norpregn-4-ene-3,20-dione 17-acetate;[(8R,9S,10R,13S,14S,17R)-17-acetyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;D9R4KSN7NA;19-Nor-17alpha-hydroxyprogesterone acetate;17-Acetoxy-19-norprogesterone;19-Norpregn-4-ene-3,20-dione, 17-(acetyloxy)-;EINECS 250-882-8;(8R,9S,10R,13S,14S,17R)-17-Acetyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate;19-Norpregn-4-ene-3,20-dione, 17-hydroxy-, acetate;EC 250-882-8;17alpha-Hydroxy-19norprogesterone-17alpha acetate;17alpha-Hydroxy-19-norprogesterone-17alpha acetate;Gestonoronacetate;UNII-D9R4KSN7NA;NIOSH/RC8960650;SCHEMBL10954178;17-Acetyloxy-19-norprogesterone;DTXSID90953874;17alpha-Acetoxy-19-norprogesterone;BCP17003;17-alpha-Acetoxy-19-norprogesterone;AKOS015896562;RC89606500;17-Acetyl-3-oxoestr-4-en-17-yl acetate #;17.ALPHA.-ACETOXY-19-NORPROGESTERONE;A821085;17-alpha-Hydroxy-19-norpregn-4-ene-3,20-dione acetate;19-Norpregn-4-ene-3,20-dione, 17-alpha-hydroxy-, acetate;(8R,9S,10R,13S,14S,17R)-17-Acetyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ylacetate;[(8R,9S,10R,13S,14S,17R)-17-ethanoyl-13-methyl-3-oxidanylidene-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] ethanoate;acetic acid [(8R,9S,10R,13S,14S,17R)-17-acetyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] ester

Chemical Property of 17-Hydroxy-19-norpregn-4-ene-3,20-dione 17-acetate

Chemical Property:

• Vapor Pressure: 9.35E-10mmHg at 25°C
• Melting Point: 228-230 °C
• Refractive Index: 1.545
• Boiling Point: 490.2 °C at 760 mmHg
• Flash Point: 212.8 °C
• PSA: 60.44000
• Density: 1.16 g/cm³
• LogP: 4.01910
• Water Solubility.: 3.62mg/L at 20℃
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 358.21440943
• Heavy Atom Count: 26
• Complexity: 692

Purity/Quality:

99% ^*data from raw suppliers

(8R,9S,10R,13S,14S,17R)-17-Acetyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ylacetate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)OC(=O)C
• Isomeric SMILES: CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)OC(=O)C

Technology Process of 17-Hydroxy-19-norpregn-4-ene-3,20-dione 17-acetate

There total 29 articles about 17-Hydroxy-19-norpregn-4-ene-3,20-dione 17-acetate 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: 95.0%

17-alpha-Hydroxy-19-norprogesterone (2137-18-0) + acetic anhydride (108-24-7) → 17α-acetoxy-19-norpregna-4-ene-3,20-dione (31981-44-9)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 24h;

DOI:10.1021/op4003533

Reference yield: 82.36%

Isopropenyl acetate (108-22-5) + 17-alpha-Hydroxy-19-norprogesterone (2137-18-0) → 17α-acetoxy-19-norpregna-4-ene-3,20-dione (31981-44-9)

Guidance literature:

Isopropenyl acetate; 17-alpha-Hydroxy-19-norprogesterone; With toluene-4-sulfonic acid; In dichloromethane; chloroform; at 58 - 60 ℃; for 2h;

With hydrogenchloride; In dichloromethane; chloroform; water; at 60 ℃; Solvent; Temperature;

Reference yield:

17α-hydroxy-3-methoxy-19-norpregna-1,3,5(10)-trien-20-one (1624-58-4) → 17α-acetoxy-19-norpregna-4-ene-3,20-dione (31981-44-9)

Guidance literature:

Multi-step reaction with 4 steps

1: benzene; toluene-4-sulfonic acid / Entfernen des entstehenden Wassers

2: diethyl ether; lithium; liquid ammonia / anschliessend Behandeln mit Aethanol

3: methanol.HCl

4: toluene-4-sulfonic acid / und Behandeln des Reaktionsprodukts mit methanol.KOH

With hydrogenchloride; diethyl ether; ammonia; lithium; toluene-4-sulfonic acid; benzene;

DOI:10.1021/ja01555a053

upstream raw materials:

17-alpha-Hydroxy-19-norprogesterone

acetic anhydride

17α-hydroxy-3-methoxy-19-norpregna-1,3,5(10)-trien-20-one

3-hydroxy-19-norpregna-1,3,5⁽¹⁰⁾,16-tetraen-20-one

Downstream raw materials:

17α-acetoxy-6-methylene-19-norpregn-4-ene-3,20-dione

nomegestrol acetate

Refernces

• 1、 Lu, He-Lin,Wu, Zong-Wen,Song, Shu-Yong,Liao, Xiao-Dan,Zhu, Yan,Huang, Yun-Sheng. "An improved synthesis of nomegestrol acetate". . p. 431 - 436. Retrieved 2014/04/17.