Synthesis, X-ray, DFT and antibacterial activity of a novel 1-indanone derivative

• Oxabicyclo[2.2.1] heptene was synthesized via intramolecular Diels-Alder cycloaddition of furan. • The structure of the reaction product 11 (CCDC number: 2391,391) in the cycloaddition model was determined by X-ray structure. • Introducing substituents into the aromatic ring resulted in the formation of both cyclization and dimerization products. 1-Indanone is a prominent scaffold recognized for its wide range of biological activities. Numerous studies have demonstrated that 1-indanone derivatives are crucial for Alzheimer's disease, antidiarrheal, anti-proliferative, antibacterial, anti-inflammatory, anticancer agents, etc. In recent years, it has been found that this type of compound also has significant anti-plant disease activity. Novel 1-indanone derivatives were designed and synthesized based on their extensive biological activities. The compounds were characterized using 1 H NMR, 13 C NMR, and high-resolution mass spectrometry (HRMS). Compound 11 (CCDC number: 2391,391) was crystallized, and its structure was determined through X-ray analysis. Additionally, density functional theory (DFT) calculations for compound 11 were conducted at the B3LYP/6–311 level. Ultimately, systematic biological assays indicated that the intermediate 6 exhibited significant inhibitory activity in vitro against the four tested plant pathogenic bacteria. A novel 1-indanone derivative was synthesized, and compound 11 ′s structures were calculated by DFT. The structure of compound 11 by a DFT method was compared with the X-ray structure. The compound 6 exhibited significant inhibitory activity in vitro against the four tested plant pathogenic bacteria.