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

• ChemBase ID: 165261
• Molecular Formular: C23H25FN2O2
• Molecular Mass: 380.4552032
• Monoisotopic Mass: 380.19000627
• SMILES: c1(ccccc1/C=C/C(=O)N[C@H](c1ccc2c(c1)N(CCO2)CC1CC1)C)F
• Canonical SMILES: O=C(N[C@H](c1ccc2c(c1)N(CCO2)CC1CC1)C)/C=C/c1ccccc1F
• InChI: InChI=1S/C23H25FN2O2/c1-16(25-23(27)11-9-18-4-2-3-5-20(18)24)19-8-10-22-21(14-19)26(12-13-28-22)15-17-6-7-17/h2-5,8-11,14,16-17H,6-7,12-13,15H2,1H3,(H,25,27)/b11-9+/t16-/m0/s1
• InChIKey: IDFFOPPWSLCCAA-SOGBHIHOSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 697287-41-5
• PubChem SID: 162259394
• PubChem CID: 10452369

CALCULATED PROPERTIES

• Acid pKa: 14.876624
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.395796
• LogD (pH = 7.4): 4.3959923
• Log P: 4.3959947
• Molar Refractivity: 109.8914 cm^3
• Polarizability: 41.225086 Å^3
• Polar Surface Area: 41.57 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 180-182°C

DETAILS

Toronto Research Chemicals - C988700

A potent and efficacious KCNQ2 opener which inibits induced hyperexcitability of rat hippocampal neurons.

REFERENCES

• Wu, Y-J., et al.: Bioorg & Medicinal Chemistry Letters, 14, 1991 (2004)