methyl (2R,7R,10S,11S,14R,15S)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.02,7.011,15]heptadec-3-ene-14-carboxylate

• ChemBase ID: 175989
• Molecular Formular: C20H29NO3
• Molecular Mass: 331.44916
• Monoisotopic Mass: 331.21474379
• SMILES: C1=CC(=O)N[C@H]2[C@]1(C1[C@@H](CC2)[C@H]2[C@](CC1)([C@@H](CC2)C(=O)OC)C)C
• Canonical SMILES: COC(=O)[C@@H]1CC[C@@H]2[C@]1(C)CCC1[C@H]2CC[C@@H]2[C@]1(C)C=CC(=O)N2
• InChI: InChI=1S/C20H29NO3/c1-19-10-8-14-12(13(19)5-6-15(19)18(23)24-3)4-7-16-20(14,2)11-9-17(22)21-16/h9,11-16H,4-8,10H2,1-3H3,(H,21,22)/t12-,13-,14?,15-,16+,19-,20+/m0/s1
• InChIKey: WMSQGMYJYBSBKA-JNPCSKDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,7R,10S,11S,14R,15S)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-14-carboxylate
• IUPAC Traditional name: methyl (2R,7R,10S,11S,14R,15S)-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-3-ene-14-carboxylate
• Synonyms: (4aR,4bS,6aS,7S,9aS,9bS,11aR)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-Tetradecahydro-4a,6a-dimethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxylic Acid Methyl Ester; (5α,17β)-3-Oxo-4-azaandrost-1-ene-17-carboxylic Acid Methyl Ester; Methyl 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylate; Finasteride Impurity; 3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester

Database IDs

• CAS Number: 103335-41-7
• PubChem SID: 164231899
• PubChem CID: 71751366

CALCULATED PROPERTIES

• Acid pKa: 14.43019
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.7485087
• LogD (pH = 7.4): 2.7487104
• Log P: 2.748713
• Molar Refractivity: 92.4406 cm^3
• Polarizability: 36.385227 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 280-282°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O847260

Finasteride (F342000) impurity. A novel intermediate in the synthesis of Finasteride, a 5α-reductase inhibitor used for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrog

REFERENCES

• Bakshi., et al.: J. Med. Chem., 38, 3189 (1995)