2'-(Oxiranylmethoxy)-3-phenylpropiophenone is an organic compound featuring a propiophenone core substituted at the 3-position with a phenyl group and at the 2'-position with an oxiranylmethoxy substituent. The molecular structure comprises a benzophenone-type framework where one aromatic ring is directly attached to the propiophenone moiety and the other is modified with an oxiranylmethoxy group, which is an ether linkage to an epoxide (oxirane) ring.
The propiophenone scaffold is well known in organic chemistry as a ketone derivative with various applications in synthesis and pharmaceuticals. The introduction of the phenyl substituent at the 3-position enhances the aromatic character and potential for π-π stacking interactions, influencing the compound’s chemical behavior. The oxiranylmethoxy group introduces a strained three-membered epoxide ring attached via a methoxy linker, which provides reactive functionality useful for further chemical transformations.
Synthesis of 2'-(oxiranylmethoxy)-3-phenylpropiophenone typically involves the etherification of 3-phenylpropiophenone derivatives bearing a hydroxyl group at the 2'-position. This is commonly achieved by reacting the hydroxy precursor with epichlorohydrin or other epoxide-containing reagents under basic conditions to form the oxiranylmethoxy substituent. The epoxide ring imparts electrophilic character, enabling nucleophilic ring-opening reactions that can lead to diverse functionalized products.
The presence of the oxirane ring allows this compound to serve as a useful intermediate in organic synthesis. Epoxides are known for their susceptibility to nucleophilic attack, which can occur under acidic or basic catalysis, enabling the introduction of various nucleophiles such as amines, alcohols, or thiols. This reactivity is valuable in the preparation of complex molecules, including pharmaceuticals and natural product derivatives.
From a chemical standpoint, the compound’s ketone group confers polarity and potential for enolization under suitable conditions, which may facilitate additional synthetic transformations. The phenyl substituent at the 3-position contributes to the compound’s stability and influences its electronic properties.
Applications of 2'-(oxiranylmethoxy)-3-phenylpropiophenone include its use as an intermediate in the synthesis of bioactive molecules, particularly those requiring incorporation of epoxide functionality for further elaboration. The epoxide ring enables the development of compounds with potential pharmacological activity due to its reactivity and ability to form covalent bonds with biological nucleophiles.
Analytical characterization is conducted using nuclear magnetic resonance (²H and ³C NMR) spectroscopy, which identifies aromatic proton signals, methylene and methine protons of the oxiranylmethoxy group, and signals corresponding to the ketone moiety. Infrared (IR) spectroscopy reveals characteristic absorption bands including the carbonyl stretch near 1700 cm−1 and the epoxide ring vibrations. Mass spectrometry confirms molecular weight and fragmentation patterns indicative of the epoxide and aromatic substituents.
Physically, this compound is generally a crystalline solid or viscous liquid, depending on purity and specific substitution patterns. It exhibits moderate solubility in organic solvents such as dichloromethane, ethyl acetate, and acetone, while its aqueous solubility is limited due to hydrophobic aromatic groups.
In conclusion, 2'-(oxiranylmethoxy)-3-phenylpropiophenone is a synthetically valuable molecule combining a propiophenone core with a reactive oxiranylmethoxy substituent. Its chemical structure enables diverse functionalizations through epoxide ring-opening reactions and aromatic ketone chemistry, making it a useful intermediate in organic synthesis and the development of bioactive compounds.
References
2003. Propafenone. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-16-0213
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