6-chloro-4-[2-(2-methylcyclopropyl)ethynyl]-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one

• ChemBase ID: 173619
• Molecular Formular: C15H11ClF3NO2
• Molecular Mass: 329.7015496
• Monoisotopic Mass: 329.04304094
• SMILES: c1cc(cc2c1NC(=O)OC2(C#CC1CC1C)C(F)(F)F)Cl
• Canonical SMILES: CC1CC1C#CC1(OC(=O)Nc2c1cc(Cl)cc2)C(F)(F)F
• InChI: InChI=1S/C15H11ClF3NO2/c1-8-6-9(8)4-5-14(15(17,18)19)11-7-10(16)2-3-12(11)20-13(21)22-14/h2-3,7-9H,6H2,1H3,(H,20,21)
• InChIKey: VTRDGEWILKMMRP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-4-[2-(2-methylcyclopropyl)ethynyl]-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one
• IUPAC Traditional name: 6-chloro-4-[2-(2-methylcyclopropyl)ethynyl]-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one
• Synonyms: 6-Chloro-1,4-dihydro-4-[2-(2-methylcyclopropyl)ethynyl]-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one; 6-Chloro-1,4-dihydro-4-[(2-methylcyclopropyl)ethynyl]-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one; Methyl-DMP 266; SV 997; rac Methyl Efavirenz (Mixture of Diastereomers)

Database IDs

• CAS Number: 353270-76-5
• PubChem SID: 164229529
• PubChem CID: 46782238

CALCULATED PROPERTIES

• Acid pKa: 12.523443
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.7435455
• LogD (pH = 7.4): 4.743542
• Log P: 4.7435455
• Molar Refractivity: 75.8909 cm^3
• Polarizability: 27.555042 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 162-165°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M303900

Efavirenz (E425000) potential synthetic impurity and degradation product.

REFERENCES

• Phelan, P., et al.: J. Chromatogr. Sci., 19, 13 (1981)
• Mangia, A., et al.: Anal. Chim. Acta., 149, 349 (1981)
• Careri, M., et al.: J. Chromatogr., 647, 79 (1981)
• van Beek, T., et al.: Phytochem. Anal., 6, 1 (1981)