(17|A)-17-Hydroxy-3-oxo-19-norpregna-5(10),9(11)-diene-21-nitrile

Base Information

• Chemical Name: (17|A)-17-Hydroxy-3-oxo-19-norpregna-5(10),9(11)-diene-21-nitrile
• CAS No.: 106111-42-6
• Molecular Formula: C₂₀H₂₅NO₂
• Molecular Weight: 311.424
• DSSTox Substance ID: DTXSID90569313
• Wikidata: Q82456439
• Mol file: 106111-42-6.mol

Synonyms:106111-42-6;(17|A)-17-Hydroxy-3-oxo-19-norpregna-5(10),9(11)-diene-21-nitrile;2-[(8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,4,6,7,8,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]acetonitrile;(17alpha)-17-Hydroxy-3-oxo-19-norpregna-5(10),9(11)-diene-21-nitrile;11|A-Hydroperoxy Dienogest;SCHEMBL10766445;DTXSID90569313;CHEBI:181012;(17a)-17-Hydroxy-3-oxo-19-norpregna-5(10),9(11)-diene-21-nitrile;CS-0166044;Dienogest EP Impurity C (Dienogest Impurity pound(c);17-hydroxy-3-oxo-, (17??)-19-Norpregna-5(10),9(11)-diene-21-nitrile

Chemical Property of (17|A)-17-Hydroxy-3-oxo-19-norpregna-5(10),9(11)-diene-21-nitrile

Chemical Property:

• PSA: 61.09000
• LogP: 3.83718
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 311.188529040
• Heavy Atom Count: 23
• Complexity: 679

Purity/Quality:

97% ^*data from raw suppliers

DienogestImpurityC ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC=C3C(C1CCC2(CC#N)O)CCC4=C3CCC(=O)C4
• Isomeric SMILES: C[C@]12CC=C3[C@H]([C@@H]1CC[C@]2(CC#N)O)CCC4=C3CCC(=O)C4
• Uses: Nortestosterone derivative. Often found as an impurity in Dienogest (D441870).

Technology Process of (17|A)-17-Hydroxy-3-oxo-19-norpregna-5(10),9(11)-diene-21-nitrile

There total 6 articles about (17|A)-17-Hydroxy-3-oxo-19-norpregna-5(10),9(11)-diene-21-nitrile 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: 74.0%

3'-N-Pyrrolidyl-17α-cyanomethyl-estra-3,5(10),9(11)-trien-17β-ol (106111-41-5) → 17α-Cyanomethyl-17β-hydroxy-estra-5(10),9(11)-dien-3-on (106111-42-6)

Guidance literature:

With acetic acid; In water; for 1.5h;

Reference yield:

3,3-dimethoxy-17α-cyanomethyl-17β-hydroxy-estra-5(10),9(11)-diene (102193-41-9) → 17α-Cyanomethyl-17β-hydroxy-estra-5(10),9(11)-dien-3-on (106111-42-6)

Guidance literature:

With oxalic acid; at 20 - 30 ℃;

Reference yield:

3,3-dimethoxy-17α-cyanomethyl-17β-hydroxy-estra-5(10),9(11)-diene (102193-41-9) → 17α-Cyanomethyl-17β-hydroxy-estra-5(10),9(11)-dien-3-on (106111-42-6) + Dienogest (65928-58-7)

Guidance literature:

With sulfuric acid; In water; acetonitrile; at 20 - 30 ℃; Reagent/catalyst; Solvent;

upstream raw materials:

3'-N-Pyrrolidyl-17α-cyanomethyl-estra-3,5(10),9(11)-trien-17β-ol

Dienogest

3,3-dimethoxy-17α-cyanomethyl-17β-hydroxy-estra-5(10),9(11)-diene

3,3-dimethoxy-estra-5⁽¹⁰⁾,9⁽¹¹⁾-diene-17-one

Downstream raw materials:

((8S,11S,13S,14S,17R)-11-Hydroperoxy-17-hydroxy-13-methyl-3-oxo-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-acetonitrile

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF DIENOGEST SUBSTANTIALLY FREE OF IMPURITIES". Paragraph 0026 - 0030. . Retrieved 2013/03/26.
• 2、 -. "Gonatriene derivatives and process for preparing them". . . Retrieved 2008/06/13.