methyl 2-[(3R)-3-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-hydroxypropyl]benzoate

• ChemBase ID: 164634
• Molecular Formular: C28H24ClNO3
• Molecular Mass: 457.94806
• Monoisotopic Mass: 457.14447131
• SMILES: c1c(cc2c(c1)ccc(n2)/C=C/c1cccc(c1)[C@@H](CCc1c(cccc1)C(=O)OC)O)Cl
• Canonical SMILES: COC(=O)c1ccccc1CC[C@H](c1cccc(c1)/C=C/c1ccc2c(n1)cc(cc2)Cl)O
• InChI: InChI=1S/C28H24ClNO3/c1-33-28(32)25-8-3-2-6-20(25)12-16-27(31)22-7-4-5-19(17-22)9-14-24-15-11-21-10-13-23(29)18-26(21)30-24/h2-11,13-15,17-18,27,31H,12,16H2,1H3/b14-9+/t27-/m1/s1
• InChIKey: KPCSDMZEMDMWKQ-WKMZLRSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-[(3R)-3-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-hydroxypropyl]benzoate
• IUPAC Traditional name: methyl 2-[(3R)-3-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-hydroxypropyl]benzoate
• Synonyms: 2-[(3R)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoic Acid Methyl Ester; [R-(E)]-2-[3-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]benzoic Acid Methyl Ester; 2-[3-(R)-[3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl]-3-hydroxypropyl]benzoic Acid Methyl Ester

Database IDs

• CAS Number: 150026-72-5
• PubChem SID: 162258769
• PubChem CID: 11733191

CALCULATED PROPERTIES

• Acid pKa: 14.447801
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 7.0601535
• LogD (pH = 7.4): 7.062021
• Log P: 7.0620446
• Molar Refractivity: 132.2718 cm^3
• Polarizability: 52.09115 Å^3
• Polar Surface Area: 59.42 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Yellow Foam

DETAILS

Toronto Research Chemicals - C379991

An intermediate in the synthesis of (S)-Montelukast.

REFERENCES

• Labelle, M., et al.: Bioorg. Med. Chem. Lett., 4, 463 (1994)