(2E)-N-[(1S)-1-(3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethyl]-3-(2-fluorophenyl)prop-2-enamide

• ChemBase ID: 169217
• Molecular Formular: C19H19FN2O2
• Molecular Mass: 326.3647632
• Monoisotopic Mass: 326.14305608
• SMILES: c1(ccccc1/C=C/C(=O)N[C@H](c1ccc2c(c1)NCCO2)C)F
• Canonical SMILES: O=C(N[C@H](c1ccc2c(c1)NCCO2)C)/C=C/c1ccccc1F
• InChI: InChI=1S/C19H19FN2O2/c1-13(15-6-8-18-17(12-15)21-10-11-24-18)22-19(23)9-7-14-4-2-3-5-16(14)20/h2-9,12-13,21H,10-11H2,1H3,(H,22,23)/b9-7+/t13-/m0/s1
• InChIKey: KJKISBSTHVUMEV-XOVSCCBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-N-[(1S)-1-(3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethyl]-3-(2-fluorophenyl)prop-2-enamide
• IUPAC Traditional name: (2E)-N-[(1S)-1-(3,4-dihydro-2H-1,4-benzoxazin-6-yl)ethyl]-3-(2-fluorophenyl)prop-2-enamide
• Synonyms: N-[(1S)-1-(3,4-Dihydro-2H-1,4-benzoxazin-6-yl)ethyl]-3-(2-fluorophenyl)-2-propenamide; (E)-3-(2-Fluorophenyl)-N-((S)-1-(3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-ethyl]acrylamide

Database IDs

• CAS Number: 697287-48-2
• PubChem SID: 162263349
• PubChem CID: 29980396

CALCULATED PROPERTIES

• Acid pKa: 14.7389765
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.9524662
• LogD (pH = 7.4): 2.9797919
• Log P: 2.9801517
• Molar Refractivity: 93.7146 cm^3
• Polarizability: 34.59273 Å^3
• Polar Surface Area: 50.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Light-Yellow Foam

DETAILS

Toronto Research Chemicals - F595708

A potent and efficacious KCNQ2 opener which inhibits induced hyperexcitability.

REFERENCES

• Yokoo, H., et al.: Br. J. Pharmacol., 131, 779 (2000)
• Wu, Y-J., et al.: Bioorg. Med. Chem. Lett., 14, 1991 (2000)