(1S,3S,8R,9S,10R)-9,10-Ep­oxy-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.01,3]dodeca­ne

Bimoussa, A.; Auhmani, A.; Ait Itto, M.Y.; Daran, J.-C.; Auhmani, A.

doi:10.1107/S1600536814006230

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o480

doi:10.1107/S1600536814006230

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(1S,3S,8R,9S,10R)-9,10-Epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodecane

Abdoullah Bimoussa,^a Aziz Auhmani,^a My Youssef Ait Itto,^a ^* Jean-Claude Daran ^b and Abdelwahed Auhmani ^a

^aLaboratoire de Synthése Organique et Physico-Chimie Moléculaire, Département de Chimie, Faculté des Sciences Semlalia, BP 2390 Marrakech 40000, Morocco, and ^bLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France
^*Correspondence e-mail: aititto@uca.ma

(Received 10 March 2014; accepted 20 March 2014; online 26 March 2014)

The title compound, C₁₆H₂₆O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-9-ene with metachloroperbenzoic acid. The molecule is built up from two fused six- and seven-membered rings. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. In the crystal, there are no significant intermolecular interactions present.

CCDC reference: 992783

Related literature

For the use of epoxydes in organic synthesis, see: Mori (1989 ); Paddon-Jones et al. (1997 ); Taylor et al. (1991 ). For their biological activity, see: Kupchan et al. (1989 ); Trost et al. (1983 ); Vollhardt & Schore (1996 ); Yang (2004 ). For structural discussion, see: Cremer & Pople (1975 ); Flack (1983 ); Flack & Bernardinelli (2000 ); Spek (2009 ); Boessenkool & Boyens (1980 ); Benharref et al. (2010 ). For the synthesis, see: Auhmani et al. (2001 ).

Experimental

Crystal data

C₁₆H₂₆O
M_r = 234.37
Monoclinic, P 2₁
a = 10.5563 (10) Å
b = 5.7548 (5) Å
c = 11.7096 (13) Å
β = 92.777 (8)°
V = 710.52 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 180 K
0.31 × 0.31 × 0.25 mm

Data collection

Agilent Xcalibur Eos Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.767, T_max = 1.0
8241 measured reflections
2899 independent reflections
2150 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.105
S = 1.05
2899 reflections
158 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL2013.

Supporting information

CCDC reference: 992783

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814006230/xu5778sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814006230/xu5778Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814006230/xu5778Isup3.cml

checkCIF report

Comment top

Epoxides are important synthetic intermediates that are widely used in organic synthesis. They are described in the synthesis of Antifungal products (Taylor et al., 1991) and different pheromones (Mori, 1989, Paddon-Jones et al., 1997). Besides, many natural products possess this functional group as an essential structural moiety for their biological activities (Yang, 2004; Vollhardt et al., 1996; Trost et al., 1983; Kupchan et al., 1974). Because of their widespread occurrence and synthetic utility, the development of methods for the direct asymmetric synthesis of epoxides has grown significantly. In order to prepare new epoxides with natural products, we synthesized (1S,3S,8R,9S,10R)-9,10-epoxy-3,7,7,10-tetramethyltricyclo [6.4.0.0^1,3]dodecane in three stages from β-himachalene. The title compound was prepared by treating (1S,3S,8R)-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-9-ene (Auhmani et al., 2001) by metachloroperbenzoique acide.

The title compound is built up from two fused six and seven-membered rings (Fig. 1). The six-membered-ring has an half chair conformation with puckering parameters: Q = 0.447 (3) Å, θ= 128.5 (4)° and ϕ= 171.6 (6)° (Cremer & Pople, 1975), whereas the seven-membered ring displays a boat conformation with puckering amplitudes: Q2 = 1.142 (4) and Q3 =0.036 (4) (Boessenkool & Boyens, 1980). Although the absolute configuration is different, this structure is closely related to the (1S,3S,8R,9S,10R)-2,2-Dichloro-3,7,7,10-tetramethyl-9,10-epoxytricyclo [6.4.0.0^1,3]dodecane (Benharref et al., 2010) however the seven-membered ring displays a chair conformation.

The absolute configuration (1S,3S,8R,9S,10R) is deduced from the chemical pathway. The refinement of the Flack's parameter (-0.2 (10)) (Flack, 1983; Flack & Bernardinelli, 2000) as well as the Hooft's parameter ((Spek, 2009) do not allow to define reliably the absolute configuration.

Related literature top

For the use of epoxydes in organic synthesis, see: Mori (1989); Paddon-Jones et al. (1997); Taylor et al. (1991). For their biological activity, see: Kupchan et al. (1974); Trost et al. (1983); Vollhardt & Schore (1996); Yang (2004). For structural discussion, see: Cremer & Pople (1975); Flack (1983); Flack & Bernardinelli (2000); Spek (2009); Boessenkool & Boyens (1980); Benharref et al. (2010). For the synthesis, see: Auhmani et al. (2001).

Experimental top

In 100 mL flask containing (0.220 g, 1.009 mmol) of (1S,3S,8R)-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-9-ene in 20 ml of dichloromethane was added a stoechiometric quantity of m-chloroperbenzoic acid (m-CPBA). The reaction mixture was stirred at room temperature for 2 h and then treated with 10% solution of sodium hydrogencarbonate. The reaction mixture was extracted with dichloromethane (3x 20 mL) and the organic layer were dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (230–400 mesh) with Hexane/Ethyl acetate (97:3) as eluent to give the title compound (1S,3S,8R,9S,10R)-9,10-epoxy-3,7,7,10-tetramethyltricyclo [6.4.0.0^1,3]dodecane in 72% yield. X-ray quality crystals were obtained by slow evaporation from a petroleum ether solution of the title compound.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

Figures top

Fig. 1. : Molecular view of the title compound with the atom labeling scheme. Ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

(1S,3S,8R,9S,10R)-9,10-Epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodecane top

Crystal data top

C₁₆H₂₆O	F(000) = 260
M_r = 234.37	D_x = 1.095 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1871 reflections
a = 10.5563 (10) Å	θ = 3.9–26.5°
b = 5.7548 (5) Å	µ = 0.07 mm⁻¹
c = 11.7096 (13) Å	T = 180 K
β = 92.777 (8)°	Box, colourless
V = 710.52 (12) Å³	0.31 × 0.31 × 0.25 mm
Z = 2

Data collection top

Agilent Xcalibur Eos Gemini ultra diffractometer	2899 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2150 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 16.1978 pixels mm^-1	θ_max = 26.4°, θ_min = 3.5°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −7→7
T_min = 0.767, T_max = 1.0	l = −14→14
8241 measured reflections

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0267P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2899 reflections	Δρ_max = 0.14 e Å⁻³
158 parameters	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₆H₂₆O	V = 710.52 (12) Å³
M_r = 234.37	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.5563 (10) Å	µ = 0.07 mm⁻¹
b = 5.7548 (5) Å	T = 180 K
c = 11.7096 (13) Å	0.31 × 0.31 × 0.25 mm
β = 92.777 (8)°

Data collection top

Agilent Xcalibur Eos Gemini ultra diffractometer	2899 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2150 reflections with I > 2σ(I)
T_min = 0.767, T_max = 1.0	R_int = 0.055
8241 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	1 restraint
wR(F²) = 0.105	H-atom parameters constrained
S = 1.05	Δρ_max = 0.14 e Å⁻³
2899 reflections	Δρ_min = −0.21 e Å⁻³
158 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2747 (3)	0.7760 (5)	0.3324 (3)	0.0241 (7)
C2	0.2251 (3)	0.6047 (6)	0.4168 (3)	0.0334 (8)
H2A	0.2213	0.4390	0.3941	0.040*
H2B	0.2461	0.6322	0.4990	0.040*
C3	0.1336 (3)	0.7699 (5)	0.3563 (3)	0.0276 (7)
C4	0.0457 (3)	0.6751 (6)	0.2618 (3)	0.0392 (9)
H4A	−0.0380	0.6418	0.2929	0.047*
H4B	0.0805	0.5271	0.2338	0.047*
C5	0.0281 (3)	0.8450 (7)	0.1615 (3)	0.0493 (11)
H5A	−0.0017	0.7571	0.0927	0.059*
H5B	−0.0391	0.9578	0.1791	0.059*
C6	0.1479 (3)	0.9792 (7)	0.1341 (3)	0.0429 (9)
H6A	0.1271	1.0768	0.0661	0.051*
H6B	0.1680	1.0860	0.1987	0.051*
C7	0.2684 (3)	0.8433 (6)	0.1112 (3)	0.0335 (8)
C8	0.3116 (3)	0.6867 (5)	0.2160 (3)	0.0265 (8)
H8	0.2675	0.5342	0.2043	0.032*
C9	0.4518 (3)	0.6354 (5)	0.2177 (3)	0.0295 (8)
H9	0.4857	0.5925	0.1423	0.035*
C10	0.5427 (3)	0.7440 (6)	0.2993 (3)	0.0289 (8)
C11	0.4987 (3)	0.9110 (5)	0.3879 (3)	0.0296 (8)
H11A	0.5481	1.0566	0.3826	0.036*
H11B	0.5182	0.8436	0.4645	0.036*
C12	0.3575 (3)	0.9715 (5)	0.3781 (3)	0.0274 (7)
H12A	0.3296	1.0162	0.4546	0.033*
H12B	0.3454	1.1078	0.3272	0.033*
C13	0.0746 (3)	0.9619 (6)	0.4244 (3)	0.0381 (9)
H13A	0.0582	1.0970	0.3750	0.057*
H13B	0.1328	1.0060	0.4885	0.057*
H13C	−0.0054	0.9069	0.4539	0.057*
C14	0.2449 (4)	0.6836 (8)	0.0066 (3)	0.0551 (11)
H14A	0.1789	0.5702	0.0227	0.083*
H14B	0.3235	0.6018	−0.0094	0.083*
H14C	0.2174	0.7774	−0.0599	0.083*
C15	0.3718 (3)	1.0198 (6)	0.0830 (3)	0.0460 (10)
H15A	0.3407	1.1195	0.0198	0.069*
H15B	0.4478	0.9367	0.0608	0.069*
H15C	0.3928	1.1157	0.1505	0.069*
C16	0.6798 (3)	0.7660 (7)	0.2706 (3)	0.0460 (10)
H16A	0.7340	0.7499	0.3406	0.069*
H16B	0.6939	0.9186	0.2363	0.069*
H16C	0.7007	0.6438	0.2164	0.069*
O1	0.50267 (19)	0.5041 (4)	0.31494 (19)	0.0350 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0183 (15)	0.0264 (17)	0.0278 (18)	−0.0012 (14)	0.0043 (13)	−0.0014 (15)
C2	0.0307 (19)	0.0345 (19)	0.035 (2)	0.0008 (16)	0.0051 (15)	0.0065 (16)
C3	0.0200 (16)	0.0298 (18)	0.0331 (19)	−0.0018 (15)	0.0035 (14)	0.0032 (16)
C4	0.0207 (18)	0.044 (2)	0.053 (3)	−0.0058 (16)	0.0012 (16)	−0.0024 (19)
C5	0.032 (2)	0.063 (3)	0.051 (3)	0.006 (2)	−0.0125 (18)	−0.001 (2)
C6	0.039 (2)	0.052 (2)	0.036 (2)	0.008 (2)	−0.0060 (16)	0.012 (2)
C7	0.036 (2)	0.040 (2)	0.0245 (19)	0.0031 (17)	−0.0014 (15)	0.0003 (16)
C8	0.0259 (18)	0.0267 (18)	0.0267 (19)	−0.0016 (14)	0.0000 (14)	−0.0050 (14)
C9	0.0309 (19)	0.0325 (19)	0.0254 (19)	0.0047 (16)	0.0049 (14)	0.0018 (16)
C10	0.0229 (17)	0.0339 (19)	0.0299 (19)	0.0008 (16)	0.0008 (14)	0.0046 (16)
C11	0.0251 (17)	0.034 (2)	0.0295 (19)	−0.0038 (14)	−0.0014 (14)	−0.0024 (15)
C12	0.0281 (18)	0.0302 (17)	0.0242 (18)	−0.0042 (16)	0.0028 (13)	−0.0060 (15)
C13	0.0273 (19)	0.036 (2)	0.052 (2)	0.0061 (16)	0.0123 (16)	−0.0024 (18)
C14	0.065 (3)	0.069 (3)	0.030 (2)	0.006 (2)	−0.0101 (19)	−0.010 (2)
C15	0.055 (2)	0.046 (2)	0.037 (2)	0.002 (2)	0.0087 (17)	0.0144 (18)
C16	0.0251 (19)	0.071 (3)	0.043 (2)	0.000 (2)	0.0038 (16)	−0.001 (2)
O1	0.0302 (13)	0.0314 (12)	0.0433 (15)	0.0050 (12)	0.0011 (10)	0.0018 (12)

Geometric parameters (Å, º) top

C1—C12	1.507 (4)	C9—O1	1.448 (4)
C1—C2	1.508 (4)	C9—C10	1.462 (4)
C1—C8	1.525 (4)	C9—H9	1.0000
C1—C3	1.529 (4)	C10—O1	1.458 (4)
C2—C3	1.507 (4)	C10—C11	1.504 (4)
C2—H2A	0.9900	C10—C16	1.507 (4)
C2—H2B	0.9900	C11—C12	1.530 (4)
C3—C4	1.511 (5)	C11—H11A	0.9900
C3—C13	1.514 (4)	C11—H11B	0.9900
C4—C5	1.533 (5)	C12—H12A	0.9900
C4—H4A	0.9900	C12—H12B	0.9900
C4—H4B	0.9900	C13—H13A	0.9800
C5—C6	1.529 (5)	C13—H13B	0.9800
C5—H5A	0.9900	C13—H13C	0.9800
C5—H5B	0.9900	C14—H14A	0.9800
C6—C7	1.528 (4)	C14—H14B	0.9800
C6—H6A	0.9900	C14—H14C	0.9800
C6—H6B	0.9900	C15—H15A	0.9800
C7—C15	1.538 (5)	C15—H15B	0.9800
C7—C14	1.541 (5)	C15—H15C	0.9800
C7—C8	1.573 (4)	C16—H16A	0.9800
C8—C9	1.508 (4)	C16—H16B	0.9800
C8—H8	1.0000	C16—H16C	0.9800

C12—C1—C2	118.0 (3)	O1—C9—C8	116.1 (2)
C12—C1—C8	113.6 (2)	C10—C9—C8	122.5 (3)
C2—C1—C8	118.5 (3)	O1—C9—H9	115.5
C12—C1—C3	120.4 (2)	C10—C9—H9	115.5
C2—C1—C3	59.52 (19)	C8—C9—H9	115.5
C8—C1—C3	116.7 (3)	O1—C10—C9	59.45 (19)
C3—C2—C1	60.9 (2)	O1—C10—C11	114.7 (2)
C3—C2—H2A	117.7	C9—C10—C11	120.6 (3)
C1—C2—H2A	117.7	O1—C10—C16	113.3 (3)
C3—C2—H2B	117.7	C9—C10—C16	119.9 (3)
C1—C2—H2B	117.7	C11—C10—C16	115.6 (3)
H2A—C2—H2B	114.8	C10—C11—C12	115.2 (3)
C2—C3—C4	118.3 (3)	C10—C11—H11A	108.5
C2—C3—C13	118.9 (3)	C12—C11—H11A	108.5
C4—C3—C13	113.3 (3)	C10—C11—H11B	108.5
C2—C3—C1	59.5 (2)	C12—C11—H11B	108.5
C4—C3—C1	116.3 (3)	H11A—C11—H11B	107.5
C13—C3—C1	120.6 (3)	C1—C12—C11	113.8 (2)
C3—C4—C5	112.2 (3)	C1—C12—H12A	108.8
C3—C4—H4A	109.2	C11—C12—H12A	108.8
C5—C4—H4A	109.2	C1—C12—H12B	108.8
C3—C4—H4B	109.2	C11—C12—H12B	108.8
C5—C4—H4B	109.2	H12A—C12—H12B	107.7
H4A—C4—H4B	107.9	C3—C13—H13A	109.5
C6—C5—C4	114.3 (3)	C3—C13—H13B	109.5
C6—C5—H5A	108.7	H13A—C13—H13B	109.5
C4—C5—H5A	108.7	C3—C13—H13C	109.5
C6—C5—H5B	108.7	H13A—C13—H13C	109.5
C4—C5—H5B	108.7	H13B—C13—H13C	109.5
H5A—C5—H5B	107.6	C7—C14—H14A	109.5
C7—C6—C5	118.9 (3)	C7—C14—H14B	109.5
C7—C6—H6A	107.6	H14A—C14—H14B	109.5
C5—C6—H6A	107.6	C7—C14—H14C	109.5
C7—C6—H6B	107.6	H14A—C14—H14C	109.5
C5—C6—H6B	107.6	H14B—C14—H14C	109.5
H6A—C6—H6B	107.0	C7—C15—H15A	109.5
C6—C7—C15	107.8 (3)	C7—C15—H15B	109.5
C6—C7—C14	110.0 (3)	H15A—C15—H15B	109.5
C15—C7—C14	108.2 (3)	C7—C15—H15C	109.5
C6—C7—C8	111.6 (3)	H15A—C15—H15C	109.5
C15—C7—C8	111.3 (3)	H15B—C15—H15C	109.5
C14—C7—C8	107.9 (3)	C10—C16—H16A	109.5
C9—C8—C1	110.3 (3)	C10—C16—H16B	109.5
C9—C8—C7	111.7 (2)	H16A—C16—H16B	109.5
C1—C8—C7	115.3 (2)	C10—C16—H16C	109.5
C9—C8—H8	106.3	H16A—C16—H16C	109.5
C1—C8—H8	106.3	H16B—C16—H16C	109.5
C7—C8—H8	106.3	C9—O1—C10	60.41 (19)
O1—C9—C10	60.14 (19)

Experimental details

Crystal data
Chemical formula	C₁₆H₂₆O
M_r	234.37
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	180
a, b, c (Å)	10.5563 (10), 5.7548 (5), 11.7096 (13)
β (°)	92.777 (8)
V (Å³)	710.52 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.31 × 0.31 × 0.25

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.767, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	8241, 2899, 2150
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.105, 1.05
No. of reflections	2899
No. of parameters	158
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.21

Computer programs: CrysAlis PRO (Agilent, 2012), SIR97 (Altomare et al., 1999), SHELXL2013 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012).

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