methyl (4S)-6-chloro-4-(2-cyclopropylethynyl)-2-oxo-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazine-1-carboxylate

• ChemBase ID: 164158
• Molecular Formular: C16H11ClF3NO4
• Molecular Mass: 373.7110496
• Monoisotopic Mass: 373.03287018
• SMILES: c1(ccc2c(c1)[C@@](OC(=O)N2C(=O)OC)(C#CC1CC1)C(F)(F)F)Cl
• Canonical SMILES: COC(=O)N1C(=O)O[C@](c2c1ccc(c2)Cl)(C#CC1CC1)C(F)(F)F
• InChI: InChI=1S/C16H11ClF3NO4/c1-24-13(22)21-12-5-4-10(17)8-11(12)15(16(18,19)20,25-14(21)23)7-6-9-2-3-9/h4-5,8-9H,2-3H2,1H3/t15-/m0/s1
• InChIKey: FUIGCZIMCGAKPZ-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4S)-6-chloro-4-(2-cyclopropylethynyl)-2-oxo-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazine-1-carboxylate
• IUPAC Traditional name: methyl (4S)-6-chloro-4-(2-cyclopropylethynyl)-2-oxo-4-(trifluoromethyl)-3,1-benzoxazine-1-carboxylate
• Synonyms: Methyl [4-Chloro-2-((1S)-1-trifluoromethyl-1-hydroxy-3-cyclopropyl-2-propyn-1-yl)phenyl]carbamate; SD573-Methyl Carbamate, SV993; [4-Chloro-2-[(1S)-3-cyclopropyl-1-hydroxy-1-(trifluoromethyl)-2-propynyl)phenyl]carbamic Acid Methyl Ester

Database IDs

• CAS Number: 211563-40-5
• PubChem SID: 162258293
• PubChem CID: 29975773

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.704816
• LogD (pH = 7.4): 4.704816
• Log P: 4.704816
• Molar Refractivity: 80.751 cm^3
• Polarizability: 30.320671 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Methanol
• Apperance: Light-Brown Solid

DETAILS

Toronto Research Chemicals - C365130

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

REFERENCES

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