8-(benzyloxy)-5-(2-bromoacetyl)-1,2-dihydroquinolin-2-one

• ChemBase ID: 161752
• Molecular Formular: C18H14BrNO3
• Molecular Mass: 372.21266
• Monoisotopic Mass: 371.01570531
• SMILES: c1cc(c2c(c1OCc1ccccc1)[nH]c(=O)cc2)C(=O)CBr
• Canonical SMILES: BrCC(=O)c1ccc(c2c1ccc(=O)[nH]2)OCc1ccccc1
• InChI: InChI=1S/C18H14BrNO3/c19-10-15(21)13-6-8-16(18-14(13)7-9-17(22)20-18)23-11-12-4-2-1-3-5-12/h1-9H,10-11H2,(H,20,22)
• InChIKey: RVHSDLUBNZBRMH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-(benzyloxy)-5-(2-bromoacetyl)-1,2-dihydroquinolin-2-one
• IUPAC Traditional name: 8-(benzyloxy)-5-(2-bromoacetyl)-1H-quinolin-2-one
• Synonyms: 5-(Bromoacetyl)-8-(phenylmethoxy)-2(1H)-quinolinone; 5-(2-Bromo-1-oxoethyl)-8-benzyloxy-2(1H)-quinolinone; 5-Bromoacetyl-8-benzyloxycarbostyril; 8-(Benzyloxy)-5-(bromoacetyl)quinolin-2(1H)-one; 8-Benzyloxy-5-(2-Bromoacetyl)-1H-quinolin-2-one; 8-Benzyloxy-5-bromoacetylcarbostyril; 8-Benzyloxy-5-(2-bromoacetyl)-2(1H)-quinolinone

Database IDs

• CAS Number: 100331-89-3
• PubChem SID: 162255887
• PubChem CID: 11667867

CALCULATED PROPERTIES

• Acid pKa: 12.245695
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.4444306
• LogD (pH = 7.4): 3.4444249
• Log P: 3.4444308
• Molar Refractivity: 94.4945 cm^3
• Polarizability: 34.66162 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - B286115

Used in the preparation of phenylethanolamine derivatives as β2 adrenoreceptor agonists.

REFERENCES

• Abagyan, R., et al.: J. Mol. Biol., 235, 983 (1994)
• Matsukawa, M., et al.: J. Pharm. Biomed. Anal., 17, 245 (1994)
• Cole, P., et al.: Nat. Chem. Biol., 4, 590 (1994)