2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 75589
• Molecular Formular: C15H12O2
• Molecular Mass: 224.25458
• Monoisotopic Mass: 224.08372962
• SMILES: O1c2ccccc2C(=O)CC1c1ccccc1
• Canonical SMILES: O=C1CC(Oc2c1cccc2)c1ccccc1
• InChI: InChI=1S/C15H12O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,15H,10H2
• InChIKey: ZONYXWQDUYMKFB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: flavanone; flavanone, (+-)-
• Synonyms: 2-phenylchroman-4-one; 2,3-DIHYDROFLAVONE; 2-Phenylchromanone; 2,3-Dihydro-2-phenyl-4H-1-benzopyran-4-one; (+/-)-Flavanone; 2-Phenyl-3,4-dihydro-2H-benzopyran-4-one; 2-Phenyl-3,4-dihydrobenzopyran-4-one; 2-Phenyl-4-chromanone; 4-Flavanone; NSC 50393; dl-Flavanone; Flavanone; 2,3-Dihydroflavone; Flavanone; 2,3-二氢黄酮; 黄烷酮

Database IDs

• CAS Number: 487-26-3
• EC Number: 207-654-8
• MDL Number: MFCD00006841
• Beilstein Number: 183227
• PubChem SID: 162040507; 24846563
• PubChem CID: 10251

CALCULATED PROPERTIES

• Acid pKa: 14.385588
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.095804
• LogD (pH = 7.4): 3.095804
• Log P: 3.095804
• Molar Refractivity: 65.3471 cm^3
• Polarizability: 25.451353 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 75-79°C; 76-78 °C(lit.); 76-78°C

Safety Information

• Storage Warning: Irritant
• RTECS: LK6906500
• German water hazard class: 3
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Hazard statements: H301
• GHS Precautionary statements: P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADORA3(140), CYP19A1(1588)mouse ... Hexa(15211)rat ... Adora1(29290), Ar(24208)

Product Information

• Purity: 98%; 98+%
• Empirical Formula (Hill Notation): C15H12O2
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 102032

Packaging
10 g in glass bottle

Toronto Research Chemicals - F371100

Propafenone (P757500) impurity.

REFERENCES

• Kitagawa, S., et al.: Biol. Pharm. Bull., 29, 1 (2006)
• Boccard, J., et al.: Eur. J. Pharm. Sci., 36, 254 (2006)
• Oxidation of flavanones with Iodosobenzene diacetate, B24531 and other hypervalent iodine reagents has been studied under a variety of conditions. Either the corresponding flavone or the isoflavone can be obtained depending on the solvent and acid present: J. Chem. Res., 213 (1995). If the reaction is carried out in the presence of trimethyl orthoformate, a 1,2-aryl shift occurs, and the major product becomes the methyl 2-aryl-2,3-dihydrobenzofuran-3-carboxylate: Bull. Chem. Soc. Jpn., 68, 1168 (1995).