[(10R,13S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate

Base Information

• Chemical Name: [(10R,13S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS No.: 51-98-9
• Molecular Formula: C22H28O3
• Molecular Weight: 340.463
• Hs Code.: 29372390
• NSC Number: 757248
• NCI Thesaurus Code: C702
• RXCUI: 31983
• ChEMBL ID: CHEMBL1357114
• Mol file: 51-98-9.mol

Synonyms:Aygestin;Estr-4-en-3-one, 17-(acetyloxy)-17-ethynyl-, (17beta)-;norethindrone acetate;norethindrone acetate, (17alpha)-(+-)-isomer;norethindrone acetate, (17alpha)-isomer;norethisterone acetate;Norlutate

Chemical Property of [(10R,13S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate

Chemical Property:

• Vapor Pressure: 1.87E-08mmHg at 25°C
• Melting Point: 161-162°
• Refractive Index: -34 ° (C=1, Dioxane)
• Boiling Point: 454.7 °C at 760 mmHg
• Flash Point: 197.1 °C
• PSA: 43.37000
• Density: 1.14 g/cm³
• LogP: 4.06330
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, freely soluble in methylene chloride, soluble in alcohol.
• Water Solubility.: 3.162mg/L(10 oC)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 340.20384475
• Heavy Atom Count: 25
• Complexity: 695

Purity/Quality:

99.5% ^*data from raw suppliers

Norethisterone Acetate >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40-48
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)C#C
• Isomeric SMILES: CC(=O)O[C@]1(CCC2[C@@]1(CCC3C2CCC4=CC(=O)CC[C@H]34)C)C#C
• Uses: Progesteron. Norethindrone and acetate in combination with estrogen as contraceptive (oral). It is reasonably anticipated to be a human carcinogen. Oral contraceptive (in combination with estrogen)
• Therapeutic Function: Chemical Name: 19-Nor-17α-pregn-4-en-20-yn-3one, 17-hydroxy-, acetate

Technology Process of [(10R,13S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate

There total 22 articles about [(10R,13S,17R)-17-ethynyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] 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: 96.5%

norethisterone (68-22-4) + acetic acid (64-19-7,77671-22-8) → norethisterone acetate (51-98-9)

Guidance literature:

With sodium carbonate; trifluoroacetic anhydride; In benzene; for 0.5h; Ambient temperature;

DOI:10.1016/0039-128X(85)90027-3

Reference yield: 92.0%

norethisterone (68-22-4) + acetyl chloride (75-36-5) → norethisterone acetate (51-98-9)

Guidance literature:

With pyridine; dmap; In 1,2-dichloro-ethane; at 0 ℃;

Reference yield: 91.0%

norethisterone (68-22-4) + acetic anhydride (108-24-7) → norethisterone acetate (51-98-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 50 ℃;

upstream raw materials:

3,17-diacetoxy-19-nor-17βH-pregna-3,5-dien-20-yne

norethisterone

acetic acid

acetic anhydride

Downstream raw materials:

19-norprogesterone

16α-ethyl-21-hydroxy-19-nor-pregn-4-ene-3,20-dione

17β-acetoxy-21,21-dibromo-19-nor-17α-pregn-4-ene-3,20-dione

Refernces

• 1、 Zhou, Dong,Carlson, Kathryn E.,Katzenellenbogen, John A.,Welch, Michael J.. "Bromine- and iodine-substituted 16α,17α-dioxolane progestins for breast tumor imaging and radiotherapy: Synthesis and receptor binding affinity". . p. 4737 - 4744. Retrieved 2006.
• 2、 -. "PROCESS FOR THE PURIFICATION OF NORETHINDRONE AND NORETHINDRONE ACETATE". Page/Page column 4. . Retrieved 2014/10/18.