Phenylbutanoids, commonly found in various medicinal plants, have attracted significant attention due to their remarkable biological activities, including antioxidant, anti-inflammatory, and neuroprotective effects, as well as for their versatility as starting materials in organic synthesis. Among phenylbutanoids, phenyl-1,3-butadienes represent a unique class of conjugated dienes, characterized by a phenyl (C6H5) group attached to a 1,3-butadiene (-CH=CH-CH=CH2) backbone. In this study, we synthesized the hydroxylated biphenyl 5,5′-di((E)-buta-1,3-dien-1-yl)-2,2′,3,3′-tetramethoxy-1,1′-biphenyl 1, closely related to its corresponding monomer 2, which is known for its broad range of pharmacological activities. The synthesis was carried out using microwave-assisted technologies. The structure of the synthesized compound was confirmed through elemental analysis, 13C-NMR, 1H-NMR, and ESI-MS spectrometry. Furthermore, we computed this novel compound’s conformational energy profile (CEP), evaluating how its energy varies with changes in the dihedral bond angle.

5,5′-Di((E)-buta-1,3-dien-1-yl)-2,2′,3,3′-tetramethoxy-1,1′-biphenyl

Dettori, Maria Antonietta;Fabbri, Davide
;
Dallocchio, Roberto;Carta, Paola
2025

Abstract

Phenylbutanoids, commonly found in various medicinal plants, have attracted significant attention due to their remarkable biological activities, including antioxidant, anti-inflammatory, and neuroprotective effects, as well as for their versatility as starting materials in organic synthesis. Among phenylbutanoids, phenyl-1,3-butadienes represent a unique class of conjugated dienes, characterized by a phenyl (C6H5) group attached to a 1,3-butadiene (-CH=CH-CH=CH2) backbone. In this study, we synthesized the hydroxylated biphenyl 5,5′-di((E)-buta-1,3-dien-1-yl)-2,2′,3,3′-tetramethoxy-1,1′-biphenyl 1, closely related to its corresponding monomer 2, which is known for its broad range of pharmacological activities. The synthesis was carried out using microwave-assisted technologies. The structure of the synthesized compound was confirmed through elemental analysis, 13C-NMR, 1H-NMR, and ESI-MS spectrometry. Furthermore, we computed this novel compound’s conformational energy profile (CEP), evaluating how its energy varies with changes in the dihedral bond angle.
2025
Istituto di Chimica Biomolecolare - ICB - Sede Secondaria Sassari
conformational energy profile
hydroxylated biphenyls
microwave-assisted synthesis
natural compounds
phenylbutanoids
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Descrizione: 5,5′ -Di((E)-buta-1,3-dien-1-yl)-2,2′ ,3,3′ -tetramethoxy-1,1′ -biphenyl
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.14243/558636
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