1-(5-chloro-2-{[(4-methoxyphenyl)methyl]amino}phenyl)-2,2,2-trifluoroethan-1-one

• ChemBase ID: 172887
• Molecular Formular: C16H13ClF3NO2
• Molecular Mass: 343.7281296
• Monoisotopic Mass: 343.058691
• SMILES: c1(ccc(c(c1)C(=O)C(F)(F)F)NCc1ccc(cc1)OC)Cl
• Canonical SMILES: COc1ccc(cc1)CNc1ccc(cc1C(=O)C(F)(F)F)Cl
• InChI: InChI=1S/C16H13ClF3NO2/c1-23-12-5-2-10(3-6-12)9-21-14-7-4-11(17)8-13(14)15(22)16(18,19)20/h2-8,21H,9H2,1H3
• InChIKey: BLTYAJPHEPYMJK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(5-chloro-2-{[(4-methoxyphenyl)methyl]amino}phenyl)-2,2,2-trifluoroethan-1-one
• IUPAC Traditional name: 1-(5-chloro-2-{[(4-methoxyphenyl)methyl]amino}phenyl)-2,2,2-trifluoroethanone
• Synonyms: 1-[5-Chloro-2-[[(4-methoxyphenyl)methyl]amino]phenyl]-2,2,2-trifluoroethanone; N-(4-Methoxybenzyl)-4-chloro-2-(trifluoroacetyl)aniline

Database IDs

• CAS Number: 173676-54-5
• PubChem SID: 164228797
• PubChem CID: 11089189

CALCULATED PROPERTIES

• Acid pKa: 16.20673
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.956829
• LogD (pH = 7.4): 4.956846
• Log P: 4.9568467
• Molar Refractivity: 83.5454 cm^3
• Polarizability: 30.331743 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DCM; Ethyl Acetate,
• Apperance: Yellow Solid
• Melting Point: 82-84°C

DETAILS

Toronto Research Chemicals - M261068

An intermediate in the synthesis of ent Efavirenz (E425000).

REFERENCES

• Tucker, T., et al.: J. Med. Chem., 37, 2437 (1994)
• Young, S., et al.: Antimicrob. Agents Chemother., 39, 2602 (1994)
• Quinn, T., et al.: Lancet, 348, 99 (1994)