CPrenylierung

C-Prenylierung is a chemical reaction process involving the attachment of a prenyl group (a 3-methyl-2-butenyl group) to an organic substrate, typically an aromatic compound or a heteroatom-containing molecule. This reaction is a subset of electrophilic aromatic substitution or other nucleophilic interactions, depending on the nature of the substrate and reagents used. C-Prentylation plays a significant role in the modification of natural products, pharmaceuticals, and organic syntheses, enabling the introduction of lipophilic units that can alter a compound’s biological activity or solubility.

The prenyl group, derived from isoprene units, is hydrophobic and can influence the biological properties of the modified molecule. C-Prentylation often involves reagents such as prenyl halides or prenyl alcohol derivatives, which are activated under suitable conditions—acidic, basic, or catalytic—depending on the specific reaction pathway.

This reaction can be catalyzed by acids, Lewis acids, or transition metal catalysts, facilitating the formation of a new carbon-carbon bond between the prenyl group and the substrate. Factors influencing the outcome include the type of substrate, the nature of the prenyl donor, reaction temperature, and solvent selection.

C-Prentylation is used in the synthesis of prenylated flavonoids, terpenoids, and other bioactive natural compounds. Because prenylation can enhance membrane permeability and binding affinity of pharmacologically active molecules, it has gained interest in medicinal chemistry and drug development. The reaction’s selectivity and efficiency are ongoing challenges, prompting research into catalysis and alternative methods to achieve regioselective prenylation.