(E)-2-(1,1-Di­cyclo­hexyl-3-phenyl­all­yl)-5,5-dimethyl-1,3,2-dioxaborinane

Gamal A El-Hiti; Keith Smith; Mark C Elliott; Dyfyr Heulyn Jones; Benson M Kariuki

doi:10.1107/S1600536813021739

. 2013 Aug 10;69(Pt 9):o1403. doi: 10.1107/S1600536813021739

(E)-2-(1,1-Dicyclohexyl-3-phenylallyl)-5,5-dimethyl-1,3,2-dioxaborinane

Gamal A El-Hiti ^a,^*, Keith Smith ^b, Mark C Elliott ^b, Dyfyr Heulyn Jones ^b, Benson M Kariuki ^b,^*

PMCID: PMC3884414 PMID: 24427041

Abstract

The crystal structure of the title compound, C₂₆H₃₉BO₂, which contains no strong hydrogen bond donors, displays only long C—H⋯O contacts between inversion-related pairs of molecules. The structure contains layers rich in oxygen and boron parallel to the ac plane. The dioxaborinane ring adopts an envelope conformation with the C atom attached to the two methyl groups as the flap .

Related literature

For the synthesis and applications of allylboronic esters, see: Lombardo et al. (2002 ▶); Carosi & Hall (2007 ▶); Althaus et al. (2010 ▶); Fandrick et al. (2010 ▶); Clary et al. (2011 ▶); Hesse et al. (2012 ▶); Incerti-Pradillos et al. (2013 ▶). For the X-ray structure of a boronic ester, see: Sopková-de Oliveira Santos et al. (2003 ▶).

Experimental

Crystal data

C₂₆H₃₉BO₂
M _r = 394.38
Triclinic,
a = 9.4967 (3) Å
b = 11.2837 (2) Å
c = 12.0297 (4) Å
α = 109.897 (2)°
β = 96.388 (2)°
γ = 102.048 (2)°
V = 1161.90 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 150 K
0.38 × 0.30 × 0.28 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T _min = 0.975, T _max = 0.981
8277 measured reflections
5287 independent reflections
4303 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.128
S = 1.03
5287 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP99 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CHEMDRAW Ultra (Cambridge Soft, 2001 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813021739/go2094sup1.cif

e-69-o1403-sup1.cif^{(29.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021739/go2094Isup2.hkl

e-69-o1403-Isup2.hkl^{(253.6KB, hkl)}

Click here for additional data file.^{(9.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813021739/go2094Isup3.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
C22—H22B⋯O2ⁱ	0.99	2.69	3.5773 (18)	150

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would like to extend their appreciation to the Deanship of Scientific Research at King Saud University for its funding for this research through the research group project RGP-VPP-239.

supplementary crystallographic information

1. Comment

The title compound I, a useful synthetic intermediate, was synthesized by the reaction of (E)-dicyclohexylstyrylborane with the anion of dichloromethyl methyl ether followed by esterification with 2,2-dimethyl-1,3-propanediol. Allylboronic esters have been synthesized from the reaction of lithiated carbamates with vinylboranes [Althaus et al. (2010)], and from the reaction of primary allyl halides with pinacolborane and magnesium [Incerti-Pradillos et al. (2013), Clary et al. (2011)]. Allylboronic esters are important synthetic intermediates, which have been shown to react with aldehydes to give homoallylic alcohols [Lombardo et al. (2002)], with the control of the newly-generated stereogenic centre possible through use of a chiral catalyst [Carosi et al. (2007)]. Allylboronic esters take part in a zinc alkoxide catalysed reaction with ketones to give the corresponding homoallylic alcohol products [Fandrick et al. (2010)], and also take part in a proto-deboronation reaction which has been used to synthesize the pheromone of the Californian red scale beetle [Hesse et al. (2012)]. For the X-ray structure of a boronic ester, see: Sopková-de Oliveira Santos et al. (2003).

In the molecule (Figure 1), the two cyclohexyl groups assume a chair conformation and an envelope conformation is observed for the dioxaborinane ring. The phenylallyl group is not planar as the plane through the double bond makes an angle of 20.84 ° with the phenyl group. There are no strong hydrogen bond donors in the structure. Long contacts of C—H···O type occur between pairs of molecules to form loosely bound dimers (Figure 2). The dimers are stacked along the a-axis to form a structure with layers rich in oxygen and boron parallel to the ac plane (Figure 3).