2-(5-chloro-2-{[(4-methoxyphenyl)methyl]amino}phenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol

• ChemBase ID: 164162
• Molecular Formular: C21H19ClF3NO2
• Molecular Mass: 409.8292696
• Monoisotopic Mass: 409.10564119
• SMILES: c1(ccc(c(c1)C(O)(C#CC1CC1)C(F)(F)F)NCc1ccc(cc1)OC)Cl
• Canonical SMILES: COc1ccc(cc1)CNc1ccc(cc1C(C(F)(F)F)(C#CC1CC1)O)Cl
• InChI: InChI=1S/C21H19ClF3NO2/c1-28-17-7-4-15(5-8-17)13-26-19-9-6-16(22)12-18(19)20(27,21(23,24)25)11-10-14-2-3-14/h4-9,12,14,26-27H,2-3,13H2,1H3
• InChIKey: BXJWOBQJYQHISM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(5-chloro-2-{[(4-methoxyphenyl)methyl]amino}phenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol
• IUPAC Traditional name: 2-(5-chloro-2-{[(4-methoxyphenyl)methyl]amino}phenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol
• Synonyms: SD 572; rac 5-Chloro-α-(cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-α-(trifluoromethyl)benzenemethanol; (αR)-Chloro-α-(cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-α-(trifluoromethyl)benzenemethanol; (R)-5-Chloro-α-(cyclopropylethynyl)-2-[[(4-methoxyphenyl)methyl]amino]-α-(trifluoromethyl)benzenemethanol

Database IDs

• CAS Number: 221177-56-6
• PubChem SID: 162258297
• PubChem CID: 20685453

CALCULATED PROPERTIES

• Acid pKa: 8.966102
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.1201253
• LogD (pH = 7.4): 5.108899
• Log P: 5.1205277
• Molar Refractivity: 104.3866 cm^3
• Polarizability: 38.19421 Å^3
• Polar Surface Area: 41.49 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DCM; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Solid

DETAILS

Toronto Research Chemicals - C365148

An intermediate of ent Efavirenz (E425000).

Toronto Research Chemicals - C365145

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

REFERENCES

• Kucukguzel, S., et al.: Eur. J. Med. Chem., 35, 761 (2000)
• Ren, J., et al.: Proc. Natl. Acad. Sci., 99, 14410 (2000)
• Young, S.D., et al.: Antimicrob. Ag. Chemother., 39, 2602 (1995)