(6R)-3-[(1R)-1-[3-(dibenzylamino)phenyl]propyl]-4-hydroxy-6-(2-phenylethyl)-6-(prop-1-yn-1-yl)-5,6-dihydro-2H-pyran-2-one

• ChemBase ID: 162402
• Molecular Formular: C39H39NO3
• Molecular Mass: 569.73186
• Monoisotopic Mass: 569.29299411
• SMILES: c1(cccc(c1)N(Cc1ccccc1)Cc1ccccc1)[C@H](C1=C(C[C@](OC1=O)(CCc1ccccc1)C#CC)O)CC
• Canonical SMILES: CC#C[C@@]1(CCc2ccccc2)CC(=C(C(=O)O1)[C@@H](c1cccc(c1)N(Cc1ccccc1)Cc1ccccc1)CC)O
• InChI: InChI=1S/C39H39NO3/c1-3-24-39(25-23-30-15-8-5-9-16-30)27-36(41)37(38(42)43-39)35(4-2)33-21-14-22-34(26-33)40(28-31-17-10-6-11-18-31)29-32-19-12-7-13-20-32/h5-22,26,35,41H,4,23,25,27-29H2,1-2H3/t35-,39-/m1/s1
• InChIKey: AFDVQNNCQVMKOI-JGBHCADMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-3-[(1R)-1-[3-(dibenzylamino)phenyl]propyl]-4-hydroxy-6-(2-phenylethyl)-6-(prop-1-yn-1-yl)-5,6-dihydro-2H-pyran-2-one
• IUPAC Traditional name: (6R)-3-[(1R)-1-[3-(dibenzylamino)phenyl]propyl]-4-hydroxy-6-(2-phenylethyl)-6-(prop-1-yn-1-yl)-5H-pyran-2-one
• Synonyms: [R-(R*,R*)]-3-[1-[3-[Bis(phenylmethyl)amino]phenyl]propyl]-5,6-dihydro-4-hydroxy-6-(2-phenylethyl)-6-(1-propynyl)-2H-pyran-2-one

Database IDs

• CAS Number: 188559-25-3
• PubChem SID: 162256537
• PubChem CID: 54707617

CALCULATED PROPERTIES

• Acid pKa: 7.065693
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 9.6815
• LogD (pH = 7.4): 9.194622
• Log P: 9.693981
• Molar Refractivity: 176.471 cm^3
• Polarizability: 67.25901 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Diethyl Ether; Ethyl Acetate
• Apperance: Yellow Foam

DETAILS

Toronto Research Chemicals - B522000

Intermediate for the synthesis of Tipranavir.

REFERENCES

• Judge, T. M., et al.: J. Am. Chem. Soc., 119, 3627 (1997).