(4R)-6-chloro-4-[(E)-2-cyclopropylethenyl]-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one

• ChemBase ID: 167572
• Molecular Formular: C14H11ClF3NO2
• Molecular Mass: 317.6908496
• Monoisotopic Mass: 317.04304094
• SMILES: c1cc(cc2c1NC(=O)O[C@@]2(/C=C/C1CC1)C(F)(F)F)Cl
• Canonical SMILES: FC([C@]1(/C=C/C2CC2)OC(=O)Nc2c1cc(Cl)cc2)(F)F
• InChI: InChI=1S/C14H11ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-8H,1-2H2,(H,19,20)/b6-5+/t13-/m1/s1
• InChIKey: TWWHVRKXRMMRPN-URWSZGRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-6-chloro-4-[(E)-2-cyclopropylethenyl]-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
• IUPAC Traditional name: (4R)-6-chloro-4-[(E)-2-cyclopropylethenyl]-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
• Synonyms: (4S)-6-Chloro-4-[(1E)-2-cyclopropylethenyl]-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-Benzoxazin-2-one; SR 695; (E)-Dihydro Efavirenz

Database IDs

• CAS Number: 440124-96-9
• PubChem SID: 162261705
• PubChem CID: 71316155

CALCULATED PROPERTIES

• Acid pKa: 12.592266
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.509898
• LogD (pH = 7.4): 4.5098953
• Log P: 4.509898
• Molar Refractivity: 73.0975 cm^3
• Polarizability: 26.557102 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 122-124°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D448935

(E)-Dihydro Efavirenz is an impurity of the nonnucleoside HIV-1 reverse transcriptase inhibitor Efavirenz (E425000).

REFERENCES

• Weissburg, R.P. et al.: J. Pharmac. Biomed. Anal., 28, 45 (2002)
• Ribeiro, J.A.A. et al.: J. Pharmac. Biomed. Anal., 43, 298 (2002)