(2E)-3-(3,4-Dimethoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

Abstract

In the title compound, C17H16O4, the dihedral angle between the mean planes of the hy­droxy­phenyl and dimeth­oxy­phenyl rings is 19.34 (7)°. The mean plane of the prop-2-en-1-one group, the active site in this mol­ecule, makes angles of 7.40 (8) and 13.25 (8)°, respectively, with the hy­droxy­phenyl and dimeth­oxy­phenyl rings. The crystal packing is stabilized by O—H⋯O hydrogen bonds, weak inter­molecular C—H⋯O and π–π stacking inter­actions [centroid–centroid distance = 3.7386 (9) Å].

(E)-3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

“…The bond lengths (Allen et al, 1987) and bond angles are within normal values. The bond angles C6-C7-C8 = 119.12 (14) ° and C8═C9-C10 = 127.20 (17) ° are comparable with those in a similar reported structure (E)-3- (Jasinski et al, 2011). This may be due to the presence of the keto group and associated steric forces.…”

“…For the biological activity of chalcones and chalcone derivatives, see: Marais et al (2005); Di Carlo et al (1999);Troeberg et al (2000); Ni et al (2004). For a related structure, see: Jasinski et al (2011). For the synthesis, see: Sidharthan et al (2012); Chitra et al (2013).…”

(2E)-3-(3-Benzyloxyphenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one

“…For general background and applications of chalcones, see: Awad et al (1960); Coudert et al (1988); Insuasty et al (1992Insuasty et al ( , 1997; Kolos et al (1996); Sarojini et al (2006); Shettigar et al (2010); Samshuddin et al (2010); Fun et al (2010). For related structures, see: Butcher et al (2006); Ravishankar et al (2003Ravishankar et al ( , 2005; Narayana et al (2007); Sarojini, Narayana et al (2007); ; Sharma et al (1997); Jasinski et al (2011). For hydrogen-bond motifs, see: Bernstein et al (1995).…”

“…Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al, 2006;Shettigar et al, 2010). The crystal structures of some of the related chalcones viz 1-(3,4-dimethoxyphenyl)-3-(3-methylphenyl)prop-2-en-1-one (Sharma et al, 1997), 3-(3,4-dimethoxyphenyl)-1-(4-hydroxy-phenyl)prop-2-en-1-one (Ravishankar et al, 2003), 1-(4chlorophenyl)-3-(4-hydroxyphenyl) prop-2-en-1-one (Ravishankar et al, 2005) (Sarojini, Narayana et al, 2007; and 2E (Jasinski et al, 2011) have been reported. In continuation to our studies on structures of chalcones, we report here the crystal structure of a new chalcone, the title compound.…”

In silico study, synthesis, and evaluation of the antimalarial activity of hybrid dimethoxy pyrazole 1,3,5‐triazine derivatives

“…The product was precipitated and dried, and recrystallized by the rectified spirit to get 3‐(3,4‐dimethoxyphenyl)‐1‐(4‐hydroxyphenyl)prop‐2‐en‐1‐one ( 3 ). [ 24 ]…”