11-A-Hydroxy canrenone methyl ester

Base Information

• Chemical Name: 11-A-Hydroxy canrenone methyl ester
• CAS No.: 192704-56-6
• Molecular Formula: C24H32 O6
• Molecular Weight: 416.514
• European Community (EC) Number: 606-281-1
• DSSTox Substance ID: DTXSID00348419
• Nikkaji Number: J1.889.568D
• Wikidata: Q82123207
• Mol file: 192704-56-6.mol

Synonyms:11-A-Hydroxy canrenone methyl ester;192704-56-6;11-alpha-Hydroxy canrenone methyl ester;methyl (7R,8S,9S,10R,11R,13S,14S,17R)-11-hydroxy-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-carboxylate;(2'R,7R,8S,9S,10R,11R,13S,14S)-methyl 11-hydroxy-10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate;11alpha-Hydroxymexrenone;DTXSID00348419;BDBM225710;CS340;MFCD18252911;AKOS015920011;DS-1070;CS-0158285;C73669;(2'R,7R,8S,9S,10R,11R,13S,14S)-methyl11-hydroxy-10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate;methyl (1'S,2R,2'R,9'R,10'S,11'S,15'S,17'R)-17'-hydroxy-2',15'-dimethyl-5,5'-dioxospiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan]-6'-ene-9'-carboxylate;methyl (1R,3aS,3bS,4R,9aR,9bS,10R,11aS)-10-hydroxy-9a,11a-dimethyl-5',7-dioxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydrospiro[cyclopenta[a]phenanthrene-1,2'-oxolane]-4-carboxylate;Methyl (7R,8S,9S,10R,11R,13S,14S,17R)-11-hydroxy-10,13-dimethyl-3,5'-dioxo-1,2,3,4',5',6,7,8,9,10,11,12,13,14,15,16-hexadecahydro-3'H-spiro[cyclopenta[a]phenanthrene-17,2'-furan]-7-carboxylate;Pregn-4-ene-7,21-dicarboxylic acid, 11,17-dihydroxy-3-oxo-, gamma-lactone, methyl ester, (7alpha,11alpha,17alpha)-

Chemical Property of 11-A-Hydroxy canrenone methyl ester

Chemical Property:

• Boiling Point: 604.5±55.0 °C(Predicted)
• PKA: 14.40±0.70(Predicted)
• PSA: 89.90000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 2.96400
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 416.21988874
• Heavy Atom Count: 30
• Complexity: 847

Purity/Quality:

99% ^*data from raw suppliers

11α-HydroxyMexrenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CC(C3C2C(CC4(C3CCC45CCC(=O)O5)C)O)C(=O)OC
• Isomeric SMILES: C[C@]12CCC(=O)C=C1C[C@H]([C@@H]3[C@@H]2[C@@H](C[C@]4([C@H]3CC[C@@]45CCC(=O)O5)C)O)C(=O)OC
• Use Description: 11-α-Hydroxy canrenone methyl ester, a chemical compound, finds applications in various fields. In the pharmaceutical industry, it plays a role as a synthetic intermediate for producing drugs and pharmaceutical compounds, particularly those related to hormone therapy and cardiovascular medications. Its chemical structure and reactivity make it valuable for drug development. Additionally, in the field of organic synthesis and medicinal chemistry, it contributes to the development of novel compounds and pharmaceutical research. Overall, 11-α-Hydroxy canrenone methyl ester serves as a key building block for the synthesis of important pharmaceuticals, enabling advancements in healthcare and medical science.

Technology Process of 11-A-Hydroxy canrenone methyl ester

There total 12 articles about 11-A-Hydroxy canrenone methyl ester 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: 80.0%

9α,11α-epoxy-17β-hydroxypregn-4-en-3-one-7α,21-dicarboxylic acid γ-lactone (209253-72-5) + methyl iodide (74-88-4) → 11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone (192704-56-6)

Guidance literature:

With potassium carbonate; In acetone; at 0 - 20 ℃;

Reference yield: 78.0%

4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile (192704-54-4) + sodium methylate (124-41-4) → 11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone (192704-56-6)

Guidance literature:

4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile; sodium methylate; for 20h; Heating / reflux;

With hydrogenchloride; In methanol; water;

Reference yield: 77.0%

methanol (67-56-1) + 4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile (192704-54-4) + sodium methylate (124-41-4) → 11β,17β-dihydroxy-7α-methoxycarbonyl-pregna-4-en-3-one-21-carboxylic acid, γ-lactone (192704-56-6)

Guidance literature:

Heating / reflux;

upstream raw materials:

4'S(4'α),7'α-hexadecahydro-11'α-hydroxy-10'β,13'β-dimethyl-3',5,20'-trioxospiro[furan-2(3H),17'β-[4,7]metheno(17H)cyclopenta[a]phenanthrene]-5'β(2'H)-carbonitrile

sodium methylate

methanol

potassium methanolate

Downstream raw materials:

17α-pregna-4,9(11)-diene-7α,21-dicarboxylic acid-17β-hydroxy-3-oxo-γ-lactone-7-methyl ester

7-methyl hydrogen 17α-hydroxy-3-oxopregna-4,11-diene-7α,21-dicarboxylate, γ-lactone

methyl hydrogen 17α-hydroxy-11α-(methylsulfonyl)oxy-3-oxopregn-4-ene-7α,21-dicarboxylate, γ-lactone

eplerenone

Refernces

• 1、 Zhang, Bin,Chen, Hongli,Tang, Huanyu,Feng, Huijin,Li, Yuanchao. "A diastereoselective synthesis of 7α-nitromethyl steroid derivative and its use for an efficient synthesis of eplerenone". . p. 1086 - 1091. Retrieved 2012/11/13.
• 2、 -. "PROCESS FOR PREPARING 7α-ALKOXYCARBONYL SUBSTITUTED STEROIDS". Page/Page column 68-69. . Retrieved 2008/06/13.