Androsta-4,16-dien-3-one, 17-(3-pyridinyl)-

Base Information

• Chemical Name: Androsta-4,16-dien-3-one, 17-(3-pyridinyl)-
• CAS No.: 154229-21-7
• Molecular Formula: C24H29 N O
• Molecular Weight: 347.5
• UNII: Z2L6XS2R7H
• DSSTox Substance ID: DTXSID90934961
• Nikkaji Number: J686.891F
• Wikipedia: %CE%944-Abiraterone
• Wikidata: Q30647364
• Pharos Ligand ID: RFF96QRACWS8
• ChEMBL ID: CHEMBL132778
• Mol file: 154229-21-7.mol

Synonyms:17-(3-pyridyl)androsta-5,16-dien-3-one;CB 7627;CB-7627;CB7627

Chemical Property of Androsta-4,16-dien-3-one, 17-(3-pyridinyl)-

Chemical Property:

• Vapor Pressure: 2.63E-10mmHg at 25°C
• Boiling Point: 504.6°Cat760mmHg
• PKA: 5.32±0.12(Predicted)
• Flash Point: 259.9°C
• PSA: 29.96000
• Density: 1.14g/cm³
• LogP: 5.60680
• Storage Temp.: 2-8°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 347.224914549
• Heavy Atom Count: 26
• Complexity: 676

Purity/Quality:

99% ^*data from raw suppliers

17-(3-Pyridinyl)-androsta-4,16-dien-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C=C1CCC3C2CCC4(C3CC=C4C5=CN=CC=C5)C
• Isomeric SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC=C4C5=CN=CC=C5)C
• Uses: 17-(3-Pyridinyl)-androsta-4,16-dien-3-one is a possible steroidal inhibitor of human cytochrome P 45017α-hydroxylase-C17,20-lyase.

Technology Process of Androsta-4,16-dien-3-one, 17-(3-pyridinyl)-

There total 16 articles about Androsta-4,16-dien-3-one, 17-(3-pyridinyl)- 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%

abiraterone (154229-19-3) → 17-(3-pyridine)-4,16-dieneandrost-3-one (154229-21-7)

Guidance literature:

With aluminum isopropoxide; In toluene; butanone; Inert atmosphere; Reflux;

Reference yield: 71.0%

3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-17-(3-pyridyl)androsta-3,5,16-triene (154229-38-6) → 17-(3-pyridine)-4,16-dieneandrost-3-one (154229-21-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; ethanol; at 65 ℃; for 48h;

DOI:10.1021/jm00013a022

Reference yield: 39.0%

3-Diethylboranylpyridine (89878-14-8) + 17-iodoandrosta-4,16-dien-3-one (100772-35-8) → 17-(3-pyridine)-4,16-dieneandrost-3-one (154229-21-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In tetrahydrofuran; water; for 7h; Inert atmosphere; Reflux;

DOI:10.1016/j.jsbmb.2014.01.013

upstream raw materials:

abiraterone

3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-17-(3-pyridyl)androsta-3,5,16-triene

prasterone acetate

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate

Downstream raw materials:

C₂₄H₃₀N₂O

(5aR,7aS)-5a,7a-dimethyl-8-(pyridin-3-yl)-4,5,5a,5b,6,7,7a,10,10a,10b,11,12-dodecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one

(5aR,7aS)-3,5a,7a-trimethyl-8-(pyridin-3-yl)-4,5,5a,5b,6,7,7a,10,10a,10b,11,12-dodecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one

(5aR,7aS)-3,5a,7a-trimethyl-8-(pyridin-3-yl)-2,3,4,5,5a,5b,6,7,7a,10,10a,10b,11,12-tetradecahydrocyclopenta[5,6]naphtho[1,2-d]azepine

Refernces

• 1、 Fehl, Charlie,Vogt, Caleb D.,Yadav, Rahul,Li, Kelin,Scott, Emily E.,Aubé, Jeffrey. "Structure-Based Design of Inhibitors with Improved Selectivity for Steroidogenic Cytochrome P450 17A1 over Cytochrome P450 21A2". . p. 4946 - 4960. Retrieved 2018/06/20.
• 2、 -. "ALTERING STEROID METABOLISM FOR TREATMENT OF STEROID-DEPENDENT DISEASE". Page/Page column 48. . Retrieved 2016/09/26.