29366-41-4Relevant articles and documents
Chemistry of naphthazarin derivatives 13. Conformational analysis of 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones by quantum chemistry methods
Glazunov,Berdyshev,Yakubovskaya,Pokhilo
, p. 1729 - 1736 (2006)
The molecular structures of various conformers of 2-hydroxy-1,4- naphthoquinone; 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones; 2,5,8-trihydroxy-1,4-naphthoquinone; and 3-(alk-1-enyl)-2,5,8-trihydroxy-1,4- naphthoquinones were studied by density functional theory (B3LYP/6-31(d), B3LYP/6-31(d, p)) and ab initio (MP2/6-31G, MP2/6-31(d)) methods. The strengths of the intramolecular hydrogen bonds formed by the β-hydroxy group with the O atom at C(1) and with the double bond π-electrons of the alkenyl substituents in the quinonoid rings were estimated. The compounds studied mainly exist as rotamers with the former-type hydrogen bonds. The splitting of the quinonoid bands of the stretching vibrations of the β-hydroxy group in the IR spectra of 3-(alk-1-enyl)-2-hydroxy-1,4-naphthoquinones and 3-(alk-1-enyl)-2,5,8-trihydroxy-1,4-naphthoquinones in hexane solutions is due to the existence of rotamers formed upon internal rotation of the alkenyl substituent.
Synthesis and cytotoxicity evaluation of a series of 3-alkenyl-2-hydroxy-1,4-naphthoquinones obtained by an efficient knoevenagel condensation
David, Cibelle C.,Lins, Antonio C.S.,Silva, Tania M.S.,Campos, Júlia F.,Silva, Teresinha G.,Milit?o, Gardenia C.G.,Camara, Celso A.
, p. 8 - 18 (2018/12/13)
A modified and efficient Knoevenagel condensation procedure was developed to synthesize the title compounds using β-alanine and acetic acid as catalysts, showing good to excellent yields. We used lawsone with suitable aliphatic aldehydes including isobuty
