N-[4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl]-4-methoxybenzamide

• ChemBase ID: 164163
• Molecular Formular: C21H17ClF3NO3
• Molecular Mass: 423.8127896
• Monoisotopic Mass: 423.08490575
• SMILES: c1(ccc(c(c1)C(O)(C#CC1CC1)C(F)(F)F)NC(=O)c1ccc(cc1)OC)Cl
• Canonical SMILES: COc1ccc(cc1)C(=O)Nc1ccc(cc1C(C(F)(F)F)(C#CC1CC1)O)Cl
• InChI: InChI=1S/C21H17ClF3NO3/c1-29-16-7-4-14(5-8-16)19(27)26-18-9-6-15(22)12-17(18)20(28,21(23,24)25)11-10-13-2-3-13/h4-9,12-13,28H,2-3H2,1H3,(H,26,27)
• InChIKey: QVQIJMIAFKHTFS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl]-4-methoxybenzamide
• IUPAC Traditional name: N-[4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl]-4-methoxybenzamide
• Synonyms: SW 965; rac N-[4-Chloro-2-[3-cyclopropyl-1-hydroxy-1-(trifluoromethyl)-2-propynyl]phenyl]-4-methoxybenzamide

Database IDs

• PubChem SID: 162258298
• PubChem CID: 46780976

CALCULATED PROPERTIES

• Acid pKa: 8.849016
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.014967
• LogD (pH = 7.4): 5.000004
• Log P: 5.0151615
• Molar Refractivity: 105.1137 cm^3
• Polarizability: 38.317097 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C365150

An impurity arising in the synthesis of Efavirenz (E425000).

REFERENCES

• Young, S.D., et al.: Antimicrob. Ag. Chemother., 39, 2602 (1995)