2phenylchroman4one

2-phenylchroman-4-one, commonly referred to as flavanone, is the parent compound of the flavanone class of flavonoids. The molecule consists of a chroman-4-one core with a phenyl substituent at the 2-position, giving the 2-phenylchroman-4-one skeleton. In many chemical contexts the term flavanone denotes this unsubstituted parent structure, with various natural and synthetic derivatives built on it.

Structure and classification: The core is a benzopyran-4-one ring system bearing a phenyl group at C-2. In the flavanone family, the bond between C-2 and C-3 is saturated (2,3-dihydro), distinguishing it from related flavones which contain an unsaturated C-2–C-3 bond.

Occurrence and significance: Flavanones occur widely in the plant kingdom and are among the core scaffolds of flavonoids. They are associated with many fruits and other plant tissues, where they exist as aglycones or glycosides. The parent structure serves as a basis for numerous natural products and serves as a versatile starting point in synthetic and medicinal chemistry.

Synthesis and reactivity: Flavanones can be prepared by cyclization of o-hydroxychalones to form the saturated heterocycle, or by reduction of the corresponding flavones. The core can undergo oxidation to form flavones (introducing unsaturation at the C-2–C-3 bond) or participate in various substitutions on the aromatic rings.

Applications: As a versatile scaffold, 2-phenylchroman-4-one is used in medicinal chemistry and natural product synthesis. Its derivatives display a range of biological activities, and the core structure is a common starting point for synthetic elaboration toward more complex flavonoids.