(E)-2-Meth­oxy-4-(3-oxobut-1-en­yl)phenyl acetate

Huoyun Zhang; Shuqin Li; Xiaopeng Shi

doi:10.1107/S1600536808021417

. 2008 Jul 16;64(Pt 8):o1507. doi: 10.1107/S1600536808021417

(E)-2-Methoxy-4-(3-oxobut-1-enyl)phenyl acetate

Huoyun Zhang ^a,^*, Shuqin Li ^a, Xiaopeng Shi ^a

PMCID: PMC2962134 PMID: 21203216

Abstract

The title compound, C₁₃H₁₄O₄, belongs to the class of α,β-unsaturated ketones, which have potential bactericidal, fungicidal, antitumor and anti-inflammatory properties. The C atoms and attached H atoms of the ethenyl part of the title molecule are disordered over two orientations with refined occupancies of 0.583 (7) and 0.417 (3). Molecules are connected by two intermolecular C—H⋯O interactions, forming a dimer with Inline graphic symmetry.

Related literature

For related literature, see: Steiner et al. (1998 ▶); Kuo et al. (2005 ▶); Buszek et al. (2007 ▶); Yarishkin et al. (2008 ▶); Etter et al. (1990 ▶). graphic file with name e-64-o1507-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₄O₄
M _r = 234.24
Triclinic,
a = 6.2534 (5) Å
b = 7.5797 (5) Å
c = 13.9718 (8) Å
α = 96.611 (2)°
β = 91.487 (2)°
γ = 110.599 (2)°
V = 614.21 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 299 (2) K
0.30 × 0.23 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T _min = 0.981, T _max = 0.989
3984 measured reflections
2381 independent reflections
1423 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.220
S = 1.10
2381 reflections
173 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021417/fb2101sup1.cif

e-64-o1507-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021417/fb2101Isup2.hkl

e-64-o1507-Isup2.hkl^{(116.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.58	3.507 (4)	172

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to Xiangfan University for financial support.

supplementary crystallographic information

Comment

The title compound belongs to α,β-unsaturated ketones having potential bactericidal, fungicidal, antitumor and antiinflammatory properties (Kuo et al., 2005; Yarishkin et al., 2008). Sythesis of α,β-unsaturated ketones is being extensively investigated (Buszek et al., 2007). The molecular structure is shown in Fig. 1. The molecules form dimers by a pair of intermolecular C—H···O hydrogen bonds (Steiner et al., 1998) forming a graph-set R²₂(14) (Etter et al., 1990).

Experimental

(E)-4-(4-Hydroxy-3-methoxyphenyl)but-3-en-2-one (1.92 g, 0.01 mol) and Et₃N (1.21 g, 0.012 mol) was dissolved in dry CH₂Cl₂ (50 ml). Acetyl chloride (1.02 g, 0.012 mol) was slowly added (ten minutes) to this solution by a syringe. The mixture was stirred at room temperature until the disappearance of ketone (monitored by thin layer chromatography). Then the mixture was poured into 50 ml brine and extracted with CH₂Cl₂ (40 ml). The organic layer was combined and dried over anhydrous Na₂SO₄. Removal of the solvent under reduced pressure and purification of the residue by recrystallization gave the title compound (2.1 g, yield 90%). The colourless crystals (average dimensions 0.3 mm × 0.2 mm × 0.2 mm) suitable for X-ray data collection were obtained by slow evaporation of a CH₂Cl₂ and MeOH solution in a ratio 4:1 at 293 K.