Bexlosteride

Base Information

• Chemical Name: Bexlosteride
• CAS No.: 148905-78-6
• Molecular Formula: C₁₄H₁₆ClNO
• Molecular Weight: 249.74
• UNII: 36X732P4P0
• DSSTox Substance ID: DTXSID00869972
• Nikkaji Number: J533.755K
• Wikipedia: Bexlosteride
• Wikidata: Q4899812
• NCI Thesaurus Code: C166644
• Pharos Ligand ID: LPBKQWA9J2M9
• ChEMBL ID: CHEMBL24955
• Mol file: 148905-78-6.mol

Synonyms:8-chloro-4-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo(f)quinolin-3(2H)-one;Benzo(f)quinolin-3(2H)-one, 8-chloro-1,4,4a,5,6,10b-hexahydro-4-methyl-, trans-;LY 191704;LY-191704;8-chloro-1,4,4a,5,6,10b-hexahydro-4-methylbenzo(f)quinolin-3(2H)-one;LY 300502;LY-300502

Chemical Property of Bexlosteride

Chemical Property:

• Vapor Pressure: 4.65E-07mmHg at 25°C
• Boiling Point: 413.9°Cat760mmHg
• Flash Point: 204.1°C
• PSA: 20.31000
• Density: 1.202g/cm³
• LogP: 2.92850
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 249.0920418
• Heavy Atom Count: 17
• Complexity: 319

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1C2CCC3=C(C2CCC1=O)C=CC(=C3)Cl
• Isomeric SMILES: CN1[C@@H]2CCC3=C([C@H]2CCC1=O)C=CC(=C3)Cl
• Uses: Treatment of prostate cancer (inhibits human type I isoform of 5 - reductase).

Technology Process of Bexlosteride

There total 32 articles about Bexlosteride 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: 100.0%

(2R,3R)-2,3-Bis-(4-methyl-benzoyloxy)-succinic acid; compound with 3-((1R,2R)-6-chloro-2-methylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionic acid methyl ester → bexlosteride (146117-78-4,148905-78-6)

Guidance literature:

With sodium hydrogencarbonate; In toluene; at 25 ℃; for 0.5h;

DOI:10.1021/jo9601425

Reference yield: 97.0%

(2R,3R)-2,3-Bis-(4-methyl-benzoyloxy)-succinic acid; compound with 3-((1S,2S)-6-chloro-2-methylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionic acid methyl ester → (+)-LY191704 (146117-78-4,148905-78-6)

Guidance literature:

With sodium hydrogencarbonate; In toluene; at 25 ℃; for 0.5h;

DOI:10.1021/jo9601425

Reference yield: 90.8%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3S)-2,3-Bis-(4-methyl-benzoyloxy)-succinic acid; compound with 3-((1R,2R)-6-chloro-2-methylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionic acid methyl ester → bexlosteride (146117-78-4,148905-78-6) + methyl 3-<(2-R-N-tert-butyloxycarbonylmethylamino-6-chloro-S-1,2,3,4-tetrahydronaphthalen)-1-yl>propionate (161320-13-4)

Guidance literature:

With sodium hydrogencarbonate; In toluene; for 2h;

DOI:10.1002/jlcr.2580341004

upstream raw materials:

8-chloro-4-methyl-1,2,3,4,5,6-hexahydrobenzo[f]quinolin-3-one

methylene chloride

trans-dl-8-chloro-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

1-(6-chloro-3,4-dihydro-2-naphthyl)-pyrrolidine

Refernces

• 1、 Astleford, Bret A.,Audia, James E.,Deeter, Jack,Heath, Perry C.,Janisse, Samantha K.,Kress, Thomas J.,Wepsiec, James P.,Weigel, Leland O.. "Resolution of δ-lactams provides access to nonracemic benzoquinolinones: The synthesis of LY300502 and LY300503". . p. 4450 - 4454. Retrieved 2007/10/03.
• 2、 -. "Process for preparation of benzo[f]quinolinones". . . Retrieved 2008/06/13.