Synthesis of prenylated benzaldehydes and their use in the synthesis of analogs of licochalcone A was written by Kromann, Hasse;Larsen, Mogens;Boesen, Thomas;Schonning, Kristian;Nielsen, Simon Feldbaek. And the article was included in European Journal of Medicinal Chemistry in 2004.Synthetic Route of C11H13NO This article mentions the following:
A generally applicable synthesis of prenylated aromatic compounds exemplified by prenylated benzaldehydes starting from readily available acetophenones was described. The synthesized benzaldehydes were used to prepare a number of novel analogs, such as I (R = OH, R1 = H, Cl, OMe; R = H, R1 = H, OH; R = OMe, R1 = OH, OMe), of Licochalcone A, a known antibacterial compound, and for the exploration of the pharmacophoric elements that are essential for the antibacterial activity. It was shown that the hydroxyl group in the A ring is essential for the activity and that the hydroxyl group in the B ring has no influence on the antibacterial effect of Licochalcone A. Furthermore, it is shown that the prenyl group at the position 5 of the B ring also has a dominating influence on the activity. This aliphatic group can be replaced by other lipophilic long chained substituents in order to maintain the activity. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Synthetic Route of C11H13NO).
2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Synthetic Route of C11H13NO
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts