Drospirenone 6-ene

Base Information

• Chemical Name: Drospirenone 6-ene
• CAS No.: 67372-69-4
• Molecular Formula: C23H28O3
• Molecular Weight: 352.474
• European Community (EC) Number: 881-324-7
• UNII: LF6CD1LUZA
• DSSTox Substance ID: DTXSID10217728
• Nikkaji Number: J1.198.817B
• Wikidata: Q27282954
• Mol file: 67372-69-4.mol

Synonyms:Drospirenone 6-ene;67372-69-4;Drospirenone impurity D;6,7-Demethylene-6,7-dehydro Drospirenone;LF6CD1LUZA;(1'R,2'S,3'S,5S,5'S,7'S,10'S,11'R)-7',11'-dimethylspiro[oxolane-5,6'-pentacyclo[8.8.0.02,7.03,5.011,16]octadeca-15,17-diene]-2,14'-dione;delta6-Drospirenone;UNII-LF6CD1LUZA;Drospirenone impurity D [EP];Drospirenone impurity, drospirenone 6-ene- [USP];.DELTA.6-DROSPIRENONE;SCHEMBL13936413;DTXSID10217728;17beta-Hydroxy-15beta,16beta-methylene-3-oxo-17alpha-pregna-4,6-diene-21-carboxylic acid gamma-lactone;3'H-Cyclopropa(15,16)pregna-4,6,15-triene-21-carboxylic acid, 15,16-dihydro-17-hydroxy-3-oxo-, gamma-lactone, (15alpha,16alpha,17alpha)-;DROSPIRENONE IMPURITY D [EP IMPURITY];Q27282954;DROSPIRENONE IMPURITY, DROSPIRENONE 6-ENE- [USP IMPURITY];17.BETA.-HYDROXY-15.BETA.,16.BETA.-METHYLENE-3-OXO-17.ALPHA.-PREGNA-4,6-DIENE-21-CARBOXYLIC ACID .GAMMA.-LACTONE;3'H-CYCLOPROPA(15,16)PREGNA-4,6,15-TRIENE-21-CARBOXYLIC ACID, 15,16-DIHYDRO-17-HYDROXY-3-OXO-, .GAMMA.-LACTONE, (15.ALPHA.,16.ALPHA.,17.ALPHA.)-

Chemical Property of Drospirenone 6-ene

Chemical Property:

• PSA: 43.37000
• LogP: 4.22600
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 352.20384475
• Heavy Atom Count: 26
• Complexity: 793

Purity/Quality:

97% ^*data from raw suppliers

6,7-Demethylene-6,7-dehydroDrospirenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1C=CC3C2CCC4(C3C5CC5C46CCC(=O)O6)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1C=C[C@@H]3[C@@H]2CC[C@]4([C@H]3[C@@H]5C[C@@H]5[C@@]46CCC(=O)O6)C
• Uses: 6,7-Demethylene-6,7-dehydro Drospirenone (Drospirenone EP Impurity D) is an intermediate in the synthesis of Drospirenone (D689500). Drospirenone impurity.

Technology Process of Drospirenone 6-ene

There total 5 articles about Drospirenone 6-ene 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: 71.27%

17-hydroxy-15β,16β-methylene-3-oxo-17α-pregna-4,6-diene-21,21-dicarboxyIic acid ethyl ester γ-lactone (889676-41-9) → 15β,16β-methylene-3-oxo-17α-pregna-4,6-diene-21,17-carbolactone (67372-69-4)

Guidance literature:

With sodium chloride; In water; N,N-dimethyl-formamide; for 8h; Heating / reflux;

Reference yield:

3-ethoxy-15β,16β-methylene-17α-pregn-3,5-diene-21,17-carbolactone (943434-07-9) → 15β,16β-methylene-3-oxo-17α-pregna-4,6-diene-21,17-carbolactone (67372-69-4)

Guidance literature:

With water; chloranil; In acetone; at 20 ℃; for 5h;

Reference yield:

3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one (82543-15-5) → 15β,16β-methylene-3-oxo-17α-pregna-4,6-diene-21,17-carbolactone (67372-69-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 82.5 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature

2: H₂ / Raney nickel / tetrahydrofuran; methanol / 760 Torr

3: CrO₃, pyridine, H₂O / 18 h / 70 °C

With pyridine; chromium(VI) oxide; potassium ethoxide; water; hydrogen; nickel; In tetrahydrofuran; methanol;

DOI:10.1021/jm00391a023

upstream raw materials:

(3S,5R,8R,9S,10R,13S,14S,15S,16S,17S)-17-(3-Hydroxy-propyl)-10,13-dimethyl-1,3,4,8,9,10,11,12,13,14,15,16,17,20-tetradecahydro-2H-cyclopropa[15,16]cyclopenta[a]phenanthrene-3,5,17-triol

3-ethoxy-15β,16β-methylene-17α-pregn-3,5-diene-21,17-carbolactone

3β,5-dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one

17α-(3-hydroxypropynyl)-15β,16β-methylene-5β-androst-6-ene-3β,5,17β-triol

Downstream raw materials:

dihydrospirorenone

17-hydroxy-6α,7α;15β,16β-bismethylene-3-oxo-17α-pregn-4-ene-21,21-carboxyIic acid γ-lactone

7α-(methoxycarbonyl)-15β,16β-methylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone

Mespirenone