144309-50-2

Basic information

• Product Name: 3-(1,3-BENZODIOXOL-5-YL)-1-(4-METHOXYPHENYL)-2-PROPEN-1-ONE
• Synonyms: 3-(1,3-BENZODIOXOL-5-YL)-1-(4-METHOXYPHENYL)-2-PROPEN-1-ONE;3-(1,3-BENZODIOXOL-5-YL)-1-(4-METHOXYPHENYL)PROP-2-EN-1-ONE;RARECHEM AM UC 0315;SALOR-INT L169552-1EA
• CAS NO: 144309-50-2
• Molecular Formula: C₁₇H₁₄O₄
• Molecular Weight: 282.29
• Mol File: 144309-50-2.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(1,3-BENZODIOXOL-5-YL)-1-(4-METHOXYPHENYL)-2-PROPEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1,3-BENZODIOXOL-5-YL)-1-(4-METHOXYPHENYL)-2-PROPEN-1-ONE(144309-50-2)
• EPA Substance Registry System: 3-(1,3-BENZODIOXOL-5-YL)-1-(4-METHOXYPHENYL)-2-PROPEN-1-ONE(144309-50-2)

Safety Data

• Hazardous Substances Data: 144309-50-2(Hazardous Substances Data)

Upstream product

• 120-57-0 piperonal 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 162256-49-7 2-benzo<1,3>dioxol-5-yl-4-(4-methoxyphenyl)-4-oxobutyric acid methyl ester 
• 162256-50-0 3-Benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one 
• 198271-01-1 3-Benzo[1,3]dioxol-5-yl-4-[3-(2-dimethylamino-ethoxy)-benzyl]-5-hydroxy-5-(4-methoxy-phenyl)-5H-furan-2-one 

Relevant articles and documents

Synthesis and evaluation of chalcone derivatives as novel sunscreen agent

Ultraviolet (UV) irradiation is a serious problem for skin health thus the interest in the research to develop sunscreen agent has been increasing. Chalcone is a promising compound to be developed as its chromophore absorbs in the UV region. Therefore, in

Hansch’s analysis application to chalcone synthesis by Claisen–Schmidt reaction based in DFT methodology

Chalcones are bioactive compounds obtained from either natural sources or synthetic procedures and widely used due to their several biological properties. The most common experimental methodology in obtaining these compounds is Claisen–Schmidt reaction, which is a particular type of aldolic condensation. In this work, we have synthesized 23 chalcones and by density functional theory (DFT) calculation, we have studied the difference in reactivity of the several benzaldehydes and their effects on the yield of this reaction. From molecular orbital descriptors were obtained two quantitative structure–reactivity relationship (QSRR) models based on Hansch’s analysis. The results of this study showed that, for the most benzaldehydes (15 of 23 compounds), their reactivity was correlated with LUMO energy and global Electrophilicity Index (ω) values, which are determined in the first step of Claisen–Schmidt condensation mechanism (nucleophilic addition). Likewise, for the smallest group of benzaldehydes, their reactivity was related to their HOMO and ΔL???H (LUMO???HOMO) energies, which were determined in the second step of the mechanism (trans-elimination). This is the first report of a QSRR model analyzing the yield of chalcone synthesis based on DFT methodology.

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

The present work describes the antibacterial and antifungal activities of several chalcones obtained by a straight Claisen-Schmidt aldol condensation determined by the minimal inhibitory concentration against different microorganisms (Gram-positive and Gram-negative bacteria and fungi). Solid state crystal structures of seven chalcones were determined by X-ray diffraction (XRD) analysis. Chemometric studies were carried out in order to identify a potential structureactivity relationship.