(E)-3-Hy­droxy-5,5-dimethyl-2-(3-phenyl­prop-2-en-1-yl)cyclo­hex-2-en-1-one

Afsaneh Zonouzi; Zakieh Izakiana; Seik Weng Ng

doi:10.1107/S160053681103220X

. 2011 Aug 17;67(Pt 9):o2337. doi: 10.1107/S160053681103220X

(E)-3-Hydroxy-5,5-dimethyl-2-(3-phenylprop-2-en-1-yl)cyclohex-2-en-1-one

Afsaneh Zonouzi ^a, Zakieh Izakiana ^a, Seik Weng Ng ^b,^c,^*

PMCID: PMC3200708 PMID: 22058958

Abstract

Five of the atoms of the six-membered cyclohexene ring of the title compound, C₁₇H₂₀O₂, are essentially coplanar (r.m.s. deviation = 0.006 Å), with the sixth (the dimethylmethyl C atom) deviating from the mean plane of the five atoms by 0.610 (2) Å. This plane is nearly perpendicular to the cinnamyl portion, the two planes being aligned at 85.1 (1)°. Two molecules are linked by an O—H⋯O hydrogen bond about a center of inversion. The cyclohexene ring is disordered over two directly overlapping positions. As a result, the hydroxy group and the keto O atom cannot be distinguished from one another.

Related literature

For the synthesis, see: Gan et al. (2008 ▶).

Experimental

Crystal data

C₁₇H₂₀O₂
M _r = 256.33
Triclinic,
a = 5.6480 (2) Å
b = 10.9077 (5) Å
c = 12.4762 (8) Å
α = 70.999 (5)°
β = 89.533 (4)°
γ = 75.783 (4)°
V = 702.31 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.977, T _max = 0.985
6734 measured reflections
3119 independent reflections
2554 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.120
S = 1.02
3119 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103220X/bt5605sup1.cif

e-67-o2337-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103220X/bt5605Isup2.hkl

e-67-o2337-Isup2.hkl^{(153KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681103220X/bt5605Isup3.cml

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
O1—H1⋯O1ⁱ	0.84	1.76	2.582 (2)	166
O2—H2⋯O2ⁱⁱ	0.84	1.74	2.569 (2)	167

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We thank the Iran National Science Foundation and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Dimedone condenses with aromatic aldehydes. Cinnamaldehyde is the aldehyde in the present study. The compound C₁₇H₂₀O₂ (Scheme I, Fig. 1) possess a hydroxy as well as a ketonic unit; these interact by an O–H···O hydrogen bond to generate a hydrogen-bonded dimer (Table 1). The synthesis illustrates the direct activation of a C–O bond of a cyclic 1,3-dione to yield the C-alkylated product; an earlier report detailed the synthesis that is catalyzed by palladium compounds (Gan et al., 2008). Five of the atoms of the six-membered cyclohexene ring of C₁₇H₂₀O₂ are coplanar, with the sixth (the dimethylmethyl carbon) deviating from the mean-plane of the five. This plane is perpendicular to the cinnamyl portion. Two molecules are linked by an O–H···O hydrogen bond about a center-of-inversion (Table 1).

Experimental

To a stirred solution of dimedone (0.68 g, 5 mmol) and cinnamaldehyde (0.66 g, 5 mmol) in ethanol (10 ml) was added zinc chloride (1 mmol) along with a small amount of a primary amine as catalyst. The mixture was heated for 12 h. The product was purified by column chromatography on silica gel by using an ethyl acetate/n-hexane (1:3) solvent system. The compound was recrystallized from ethyl acetate to give colorless crystals (yield 70%).