(4R)-6-chloro-4-(2-cyclopropylethynyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazine

• ChemBase ID: 164161
• Molecular Formular: C21H17ClF3NO2
• Molecular Mass: 407.8133896
• Monoisotopic Mass: 407.08999113
• SMILES: c1cc(cc2c1NC(O[C@@]2(C#CC1CC1)C(F)(F)F)c1ccc(cc1)OC)Cl
• Canonical SMILES: COc1ccc(cc1)C1Nc2ccc(cc2[C@](O1)(C#CC1CC1)C(F)(F)F)Cl
• InChI: InChI=1S/C21H17ClF3NO2/c1-27-16-7-4-14(5-8-16)19-26-18-9-6-15(22)12-17(18)20(28-19,21(23,24)25)11-10-13-2-3-13/h4-9,12-13,19,26H,2-3H2,1H3/t19?,20-/m1/s1
• InChIKey: UTEUZELNJWOZOI-GFOWMXPYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-6-chloro-4-(2-cyclopropylethynyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazine
• IUPAC Traditional name: (4R)-6-chloro-4-(2-cyclopropylethynyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1,2-dihydro-3,1-benzoxazine
• Synonyms: (4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-2-(4-methoxyphenyl)-4-(trifluoromethyl)-2H-3,1-benzoxazine; (4S)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-2-(4-methoxyphenyl)-4-(trifluoromethyl)-2H-3,1-benzoxazine(Mixture of 2 Diastereomers)

Database IDs

• CAS Number: 209414-26-6
• PubChem SID: 162258296
• PubChem CID: 71314705

CALCULATED PROPERTIES

• Acid pKa: 11.287471
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.918007
• LogD (pH = 7.4): 5.917954
• Log P: 5.9180074
• Molar Refractivity: 101.9064 cm^3
• Polarizability: 37.551804 Å^3
• Polar Surface Area: 30.49 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - C365140

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

REFERENCES

• Chen, C., et al.: Enantiomer, 4, 599 (1999)
• Young, S.D., et al.: Antimicrob. Ag. Chemother., 39, 2602 (1999)