(4R)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one

• ChemBase ID: 167947
• Molecular Formular: C14H9ClF3NO2
• Molecular Mass: 315.6749696
• Monoisotopic Mass: 315.02739087
• SMILES: c1cc(cc2c1NC(=O)O[C@@]2(C#CC1CC1)C(F)(F)F)Cl
• Canonical SMILES: FC([C@]1(C#CC2CC2)OC(=O)Nc2c1cc(Cl)cc2)(F)F
• InChI: InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m1/s1
• InChIKey: XPOQHMRABVBWPR-CYBMUJFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
• IUPAC Traditional name: (4R)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
• Synonyms: (4S)-6-Chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one; DMP 266; L 743726; Stocrin; Sustiva; Efavirenz

Database IDs

• CAS Number: 154598-52-4
• PubChem SID: 162262080
• PubChem CID: 477099

CALCULATED PROPERTIES

• Acid pKa: 12.523443
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.4565263
• LogD (pH = 7.4): 4.4565234
• Log P: 4.4565263
• Molar Refractivity: 71.3423 cm^3
• Polarizability: 25.755894 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 134-136°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E425000

A nonnucleoside HIV-1 reverse transcriptase inhibitor. Antiviral.

REFERENCES

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