3-Oxopregn-4-ene-21,17alpha-carbolactone

Base Information

• Chemical Name: 3-Oxopregn-4-ene-21,17alpha-carbolactone
• CAS No.: 976-70-5
• Molecular Formula: C22H30O3
• Molecular Weight: 342.478
• Hs Code.: 2932206000
• European Community (EC) Number: 213-552-4
• UNII: 3N8TCN29OP
• DSSTox Substance ID: DTXSID10875403
• Nikkaji Number: J15.025H
• Wikipedia: SC-5233
• Metabolomics Workbench ID: 144718
• ChEMBL ID: CHEMBL400534
• Mol file: 976-70-5.mol

Synonyms:976-70-5;3-Oxopregn-4-ene-21,17alpha-carbolactone;6,7-Dihydrocanrenone;20-Spirox-4-ene-3,20-dione;EINECS 213-552-4;SC 5233;SC-5233;BRN 0043765;3N8TCN29OP;(8R,9S,10R,13S,14S,17R)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-3,5'(2H,4'H)-dione;(8R,9S,10R,13S,14S,17R)-10,13-dimethylspiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione;17-alpha-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-3-oxo-, gamma-lactone;3-(3-Oxo-17-beta-hydroxy-4-androsten-17-alpha-yl)propionic acid gamma-lactone;EC 213-552-4;omega-(3-Oxo-17-beta-hydroxy-4-androsten-17-alpha-yl) propionic acid lactone;4-17-00-06330 (Beilstein Handbook Reference);(2R)-3,4-Dihydro-5H-spiro(androst-4-ene-17,2-furan)-3,5-dione;Pregn-4-ene-21-carboxylic acid, 17-hydroxy-3-oxo-, g-lactone, (17a)-;17.alpha.-Pregn-4-ene-21-carboxylic acid, 17-hydroxy-3-oxo-, .gamma.-lactone;Pregn-4-ene-21-carboxylic acid, 17-hydroxy-3-oxo-, .gamma.-lactone, (17.alpha.)-;spriolactone;Spironolactone EP impurity C;(2'R,8R,9S,10R,13S,14S)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-3,5'(2H,4'H)-dione;UNII-3N8TCN29OP;MLS001164723;CHEMBL400534;SCHEMBL18218188;DTXSID10875403;HMS2878M21;BBL033693;STK801875;AKOS005622474;CS-O-10705;3-oxopregn-4-ene-21,17a-carbolactone;NCGC00246184-01;NCGC00246184-03;SMR000539898;VS-12223;LS-118615;SPIRONOLACTONE IMPURITY C [EP IMPURITY];AB00829008-05;3-(3-OXO-17.BETA.-HYDROXYANDROST-4-EN-17.ALPHA.-YL)PROPIOLACTONE;(2'R)-3',4'-DIHYDRO-5'H-SPIRO(ANDROST-4-ENE-17,2'-FURAN)-3,5'-DIONE;17.BETA.-HYDROXY-3-OXOPREGN-4-EN-21-CARBOXYLIC ACID .GAMMA.-LACTONE;3'-(3-OXO-17.BETA.-HYDROXYANDROST-4-EN-17.ALPHA.-YL)-PROPIONIC ACID LACTONE;3-(3-OXO-17.BETA.-HYDROXY-4-ANDROSTEN-17-YL)PROPIONIC ACID .GAMMA.-LACTONE;(1R,3aS,3bR,9aR,9bS,11aS)-9a,11a-dimethyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydrospiro[cyclopenta[a]phenanthrene-1,2'-oxolane]-5',7-dione

Chemical Property of 3-Oxopregn-4-ene-21,17alpha-carbolactone

Chemical Property:

• Melting Point: 156-159 °C
• Boiling Point: 522.8±50.0 °C(Predicted)
• Flash Point: 228.9oC
• PSA: 43.37000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 4.59410
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 20.4mg/L at 20℃
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 342.21949481
• Heavy Atom Count: 25
• Complexity: 679

Purity/Quality:

99.9% ^*data from raw suppliers

6,7-Dihydrocanrenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC45CCC(=O)O5)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]45CCC(=O)O5)C
• Uses: 6,7-Dihydrocanrenone (Spironolactone EP Impurity C) is an intermediate in the synthesis of Canrenone (C175610), an aldosterone antagonist. Diuretic.

Technology Process of 3-Oxopregn-4-ene-21,17alpha-carbolactone

There total 28 articles about 3-Oxopregn-4-ene-21,17alpha-carbolactone 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: 97.0%

C24H34O4 (75219-50-0) → 3-oxopregn-4-ene-21,17α-carbolactone (976-70-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 0.5h;

DOI:10.1021/jo00282a041

Reference yield: 87.0%

17α-(3-hydroxypropyl)-17β-hydroxy-4-androsten-3-one (55542-27-3) → 3-oxopregn-4-ene-21,17α-carbolactone (976-70-5)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; potassium bromide; In dichloromethane; at 10 - 15 ℃; for 6h;

Reference yield: 80.0%

(17β)-4',5'-dihydro-5'-methoxyspiro-3-one (52520-26-0) → 3-oxopregn-4-ene-21,17α-carbolactone (976-70-5)

Guidance literature:

With jones reagent;

DOI:10.1016/S0040-4039(00)93611-6

upstream raw materials:

Allyl Tetramethylphosphorodiamidate

3-ethoxyandrosta-3,5-dien-17-one

(17β)-4',5'-dihydro-5'-methoxyspiro-3-one

C₂₄H₃₄O₄

Downstream raw materials:

canrenone

SPIRONOLACTONE

Canrenone

6,7-dihydrocanrenonoic acid

Refernces

• 1、 -. "A spironolacton intermediate testosterone for synthesizing method". . . Retrieved 2017/05/12.
• 2、 Sam,Auger,Luu-The,Poirier. "Steroidal spiro-γ-lactones that inhibit 17β-hydroxysteroid dehydrogenase activity in human placental microsomes". . p. 4518 - 4528. Retrieved 2007/10/03.