1-(3-Hy­droxy-5,8-dimeth­oxy-4-methyl-1,2,3,4-tetra­hydro-1,4-ep­oxy­naphthalen-2-yl)ethan-1-one

Lough, A.J.; Nagireddy, J.R.; Tam, W.

doi:10.1107/S1600536814007764

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o545

doi:10.1107/S1600536814007764

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1-(3-Hydroxy-5,8-dimethoxy-4-methyl-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2-yl)ethan-1-one

Alan J. Lough,^a ^* Jaipal R. Nagireddy ^b and William Tam ^b

^aDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada, and ^bDepartment of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
^*Correspondence e-mail: alough@chem.utoronto.ca

(Received 19 March 2014; accepted 7 April 2014; online 12 April 2014)

The stereochemistry and regioschemistry (exo) of the title compound, C₁₅H₁₈O₅, were determined by the X-ray analysis. The methoxy groups essentially lie in the plane of the benzene ring to which they are attached, as described by the C—O—C C torsion angles of −176.80 (12) and 4.67 (19)°. In the crystal, O—H⋯O hydrogen bonds and weak C—H⋯O hydrogen bonds link the molecules, forming chains of R₂¹(8) rings along [010].

CCDC reference: 995954

Related literature

For the metal-mediated cleavage of 2-isoxazoline rings fused to bicyclic frameworks, see: Tranmer & Tam (2002 ). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₈O₅
M_r = 278.29
Orthorhombic, P b c a
a = 10.3091 (4) Å
b = 9.1309 (4) Å
c = 29.2552 (13) Å
V = 2753.8 (2) Å³
Z = 8
Cu Kα radiation
μ = 0.84 mm⁻¹
T = 147 K
0.17 × 0.14 × 0.05 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012 ) T_min = 0.686, T_max = 0.753
9265 measured reflections
2368 independent reflections
2195 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 1.04
2368 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3ⁱ	0.97 (3)	1.89 (2)	2.8295 (15)	162 (2)
C7—H7C⋯O3ⁱ	0.98	2.42	3.3936 (19)	173
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 995954

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814007764/tk5301sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007764/tk5301Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814007764/tk5301Isup3.cml

checkCIF report

Structural commentary top

We have previously investigated the metal-mediated cleavage of 2-isoxazoline rings fused to bicyclic frameworks that are prepared in our laboratory through nitrile oxide 1,3-dipolar cycloaddition methodology (Tranmer & Tam, 2002). When expanding this study using Raney Ni, cleavage of 2-isoxazoline compound (I) (see Fig. 1) leads to the formation of β-hydroxy ketone product (II) as a single stereoisomer. The stereochemistry of the product was determined by this single-crystal X-ray analysis. Although different stereoisomers (exo and endo) could be formed, only the exo regioisomer (II) was formed.

The molecular structure of the title compound is shown in Fig. 2. The methoxy groups essentially lie in the plane of the benzene ring to which they are attached as described by the C15—O5—C12—C11 and C14—O4—C9—C10 torsion angles of -176.80 (12) and 4.67 (19)°. In the crystal, O—H···O hydrogen bonds and weak C—H···O hydrogen bonds link molecules forming chains of R¹₂(8) rings (Bernstein et al., 1995) along [010] (see Fig. 3).

Synthesis and crystallization top

To an oven dried flask containing the cycloadduct (I) (60 mg, 0.21 mmol) was added methanol (5 ml), THF (5 ml) and distilled water (2 ml) and the mixture was cooled to 273–278 K using an ice bath. AlCl₃ (87 mg, 0.65 mmol) was added to the cold solution in one portion and was stirred at 273 K for 15 minutes. Raney-nickel (0.52 g) was added and was stirred for 4 h at 273 K. The reaction mixture was filtered through a pad of celite, while washing with dichloromethane (20 ml). The organic layer was separated and the aqueous layer was extracted again with dichloromethane (10 ml), and the combined organic layers were dried over sodium sulfate then evaporated using rotary evaporation. The crude product was washed by hexanes (3 ml) followed by recrystallizaion in EtOAc:hexanes = 1:5 to give product (II) in 86% yield. X-ray quality crystals were grown from a solution of the title compound in EtOAc:hexanes = 1:5.

Refinement top

Hydrogen atoms bonded to C atoms were placed in calculated positions with C—H distances ranging from 0.95–1.00 Å and included in the refinement in a riding-model approximation with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C_methyl). The hydroxyl H atom was refined independently with an isotropic displacement parameter.

Related literature top

For the metal-mediated cleavage of 2-isoxazoline rings fused to bicyclic frameworks, see: Tranmer & Tam (2002). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The reaction scheme.
	Fig. 2. The molecular structure of the title compound showing 30% probability ellipsoids.
	Fig. 3. Part of the crystal structure with weak hydrogen bonds shown as dashed lines.

1-(3-Hydroxy-5,8-dimethoxy-4-methyl-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2-yl)ethan-1-one top

Crystal data top

C₁₅H₁₈O₅	D_x = 1.342 Mg m⁻³
M_r = 278.29	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 6136 reflections
a = 10.3091 (4) Å	θ = 5.3–66.6°
b = 9.1309 (4) Å	µ = 0.84 mm⁻¹
c = 29.2552 (13) Å	T = 147 K
V = 2753.8 (2) Å³	Plate, colourless
Z = 8	0.17 × 0.14 × 0.05 mm
F(000) = 1184

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	2195 reflections with I > 2σ(I)
Radiation source: Bruker ImuS with multi-layer optics	R_int = 0.021
ϕ and ω scans	θ_max = 66.6°, θ_min = 5.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −11→10
T_min = 0.686, T_max = 0.753	k = −6→10
9265 measured reflections	l = −34→34
2368 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0532P)² + 1.2534P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2368 reflections	Δρ_max = 0.42 e Å⁻³
189 parameters	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₈O₅	V = 2753.8 (2) Å³
M_r = 278.29	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 10.3091 (4) Å	µ = 0.84 mm⁻¹
b = 9.1309 (4) Å	T = 147 K
c = 29.2552 (13) Å	0.17 × 0.14 × 0.05 mm

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	2368 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2012)	2195 reflections with I > 2σ(I)
T_min = 0.686, T_max = 0.753	R_int = 0.021
9265 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.42 e Å⁻³
2368 reflections	Δρ_min = −0.24 e Å⁻³
189 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
O1	0.88037 (9)	0.52360 (10)	0.62898 (3)	0.0212 (2)
O2	0.70291 (9)	0.72212 (11)	0.58154 (3)	0.0259 (2)
O3	0.85382 (10)	0.46468 (11)	0.52476 (3)	0.0294 (3)
O4	0.93569 (9)	0.88101 (11)	0.72203 (3)	0.0267 (2)
O5	1.28252 (9)	0.59024 (12)	0.60787 (3)	0.0315 (3)
C1	0.99163 (13)	0.55891 (15)	0.60115 (4)	0.0212 (3)
H1A	1.0361	0.4727	0.5871	0.025*
C2	0.85197 (12)	0.67220 (14)	0.64418 (4)	0.0192 (3)
C3	0.73874 (13)	0.67520 (16)	0.67653 (4)	0.0250 (3)
H3A	0.7645	0.6323	0.7059	0.038*
H3B	0.6669	0.6185	0.6636	0.038*
H3C	0.7109	0.7767	0.6813	0.038*
C4	0.83079 (12)	0.74951 (14)	0.59729 (4)	0.0194 (3)
H4A	0.8488	0.8569	0.5994	0.023*
C5	0.93447 (13)	0.66931 (14)	0.56674 (4)	0.0204 (3)
H5A	1.0027	0.7399	0.5566	0.025*
C6	0.87214 (13)	0.59612 (15)	0.52575 (4)	0.0230 (3)
C7	0.84055 (16)	0.69186 (18)	0.48585 (5)	0.0328 (4)
H7A	0.7895	0.6362	0.4636	0.049*
H7B	0.9211	0.7256	0.4715	0.049*
H7C	0.7903	0.7766	0.4963	0.049*
C8	0.98548 (13)	0.71876 (14)	0.66166 (4)	0.0192 (3)
C9	1.02832 (13)	0.81205 (14)	0.69594 (4)	0.0212 (3)
C10	1.16170 (14)	0.82634 (16)	0.70211 (5)	0.0259 (3)
H10A	1.1935	0.8868	0.7261	0.031*
C11	1.24964 (14)	0.75349 (16)	0.67375 (5)	0.0276 (3)
H11A	1.3401	0.7656	0.6786	0.033*
C12	1.20648 (13)	0.66370 (15)	0.63864 (5)	0.0242 (3)
C13	1.07345 (13)	0.64562 (15)	0.63424 (4)	0.0213 (3)
C14	0.98079 (15)	0.98213 (16)	0.75556 (5)	0.0299 (3)
H14A	0.9064	1.0277	0.7708	0.045*
H14B	1.0333	1.0580	0.7407	0.045*
H14C	1.0337	0.9302	0.7782	0.045*
C15	1.41953 (14)	0.60214 (19)	0.61366 (6)	0.0354 (4)
H15A	1.4636	0.5488	0.5891	0.053*
H15B	1.4443	0.5603	0.6433	0.053*
H15C	1.4448	0.7055	0.6126	0.053*
H2O	0.673 (2)	0.813 (3)	0.5676 (8)	0.072 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0214 (5)	0.0188 (5)	0.0234 (5)	−0.0021 (4)	0.0009 (4)	−0.0006 (4)
O2	0.0188 (5)	0.0323 (6)	0.0267 (5)	0.0002 (4)	−0.0033 (4)	−0.0005 (4)
O3	0.0325 (6)	0.0294 (6)	0.0263 (5)	−0.0037 (4)	−0.0013 (4)	−0.0039 (4)
O4	0.0249 (5)	0.0278 (5)	0.0274 (5)	0.0002 (4)	−0.0040 (4)	−0.0091 (4)
O5	0.0177 (5)	0.0428 (6)	0.0341 (6)	0.0056 (4)	0.0026 (4)	0.0006 (5)
C1	0.0181 (7)	0.0226 (7)	0.0227 (7)	0.0012 (5)	0.0010 (5)	−0.0012 (5)
C2	0.0179 (7)	0.0183 (7)	0.0214 (6)	−0.0010 (5)	−0.0006 (5)	−0.0021 (5)
C3	0.0199 (7)	0.0322 (8)	0.0229 (7)	−0.0026 (6)	0.0019 (5)	−0.0003 (6)
C4	0.0155 (6)	0.0210 (7)	0.0217 (7)	−0.0008 (5)	−0.0009 (5)	−0.0013 (5)
C5	0.0177 (7)	0.0215 (7)	0.0221 (7)	0.0000 (5)	0.0016 (5)	0.0001 (5)
C6	0.0185 (7)	0.0280 (8)	0.0225 (7)	0.0030 (5)	0.0035 (5)	−0.0016 (6)
C7	0.0397 (9)	0.0377 (9)	0.0211 (7)	0.0107 (7)	−0.0001 (6)	−0.0010 (6)
C8	0.0183 (7)	0.0187 (6)	0.0208 (6)	−0.0008 (5)	−0.0017 (5)	0.0034 (5)
C9	0.0224 (7)	0.0198 (6)	0.0214 (6)	−0.0005 (5)	−0.0027 (5)	0.0021 (5)
C10	0.0250 (8)	0.0255 (7)	0.0271 (7)	−0.0057 (6)	−0.0075 (6)	0.0017 (6)
C11	0.0185 (7)	0.0324 (8)	0.0319 (7)	−0.0034 (6)	−0.0059 (6)	0.0063 (6)
C12	0.0184 (7)	0.0270 (7)	0.0273 (7)	0.0020 (6)	0.0004 (5)	0.0062 (6)
C13	0.0199 (7)	0.0215 (7)	0.0223 (7)	0.0008 (5)	−0.0013 (5)	0.0033 (5)
C14	0.0334 (8)	0.0292 (7)	0.0270 (7)	−0.0034 (6)	−0.0042 (6)	−0.0093 (6)
C15	0.0171 (8)	0.0468 (10)	0.0422 (9)	0.0059 (7)	0.0030 (6)	0.0146 (7)

Geometric parameters (Å, º) top

O1—C1	1.4431 (16)	C5—C6	1.5157 (18)
O1—C2	1.4576 (16)	C5—H5A	1.0000
O2—C4	1.4187 (16)	C6—C7	1.494 (2)
O2—H2O	0.97 (3)	C7—H7A	0.9800
O3—C6	1.2153 (18)	C7—H7B	0.9800
O4—C9	1.3750 (17)	C7—H7C	0.9800
O4—C14	1.4252 (16)	C8—C13	1.3827 (19)
O5—C12	1.3692 (17)	C8—C9	1.3880 (19)
O5—C15	1.4268 (18)	C9—C10	1.393 (2)
C1—C13	1.5086 (19)	C10—C11	1.397 (2)
C1—C5	1.5417 (18)	C10—H10A	0.9500
C1—H1A	1.0000	C11—C12	1.387 (2)
C2—C3	1.5030 (18)	C11—H11A	0.9500
C2—C8	1.5286 (18)	C12—C13	1.387 (2)
C2—C4	1.5581 (18)	C14—H14A	0.9800
C3—H3A	0.9800	C14—H14B	0.9800
C3—H3B	0.9800	C14—H14C	0.9800
C3—H3C	0.9800	C15—H15A	0.9800
C4—C5	1.5740 (18)	C15—H15B	0.9800
C4—H4A	1.0000	C15—H15C	0.9800

C1—O1—C2	97.11 (9)	C6—C7—H7A	109.5
C4—O2—H2O	106.0 (14)	C6—C7—H7B	109.5
C9—O4—C14	116.88 (11)	H7A—C7—H7B	109.5
C12—O5—C15	116.83 (12)	C6—C7—H7C	109.5
O1—C1—C13	101.51 (10)	H7A—C7—H7C	109.5
O1—C1—C5	102.17 (10)	H7B—C7—H7C	109.5
C13—C1—C5	106.84 (11)	C13—C8—C9	120.45 (12)
O1—C1—H1A	114.9	C13—C8—C2	105.20 (11)
C13—C1—H1A	114.9	C9—C8—C2	134.34 (12)
C5—C1—H1A	114.9	O4—C9—C8	117.45 (12)
O1—C2—C3	111.41 (11)	O4—C9—C10	124.81 (12)
O1—C2—C8	100.38 (10)	C8—C9—C10	117.72 (13)
C3—C2—C8	118.92 (11)	C9—C10—C11	121.26 (13)
O1—C2—C4	100.44 (10)	C9—C10—H10A	119.4
C3—C2—C4	115.93 (11)	C11—C10—H10A	119.4
C8—C2—C4	107.14 (10)	C12—C11—C10	120.85 (13)
C2—C3—H3A	109.5	C12—C11—H11A	119.6
C2—C3—H3B	109.5	C10—C11—H11A	119.6
H3A—C3—H3B	109.5	O5—C12—C13	116.53 (12)
C2—C3—H3C	109.5	O5—C12—C11	126.35 (13)
H3A—C3—H3C	109.5	C13—C12—C11	117.12 (13)
H3B—C3—H3C	109.5	C8—C13—C12	122.49 (13)
O2—C4—C2	109.65 (10)	C8—C13—C1	105.01 (11)
O2—C4—C5	111.38 (10)	C12—C13—C1	132.43 (13)
C2—C4—C5	101.19 (10)	O4—C14—H14A	109.5
O2—C4—H4A	111.4	O4—C14—H14B	109.5
C2—C4—H4A	111.4	H14A—C14—H14B	109.5
C5—C4—H4A	111.4	O4—C14—H14C	109.5
C6—C5—C1	112.97 (11)	H14A—C14—H14C	109.5
C6—C5—C4	111.50 (11)	H14B—C14—H14C	109.5
C1—C5—C4	101.12 (10)	O5—C15—H15A	109.5
C6—C5—H5A	110.3	O5—C15—H15B	109.5
C1—C5—H5A	110.3	H15A—C15—H15B	109.5
C4—C5—H5A	110.3	O5—C15—H15C	109.5
O3—C6—C7	121.69 (13)	H15A—C15—H15C	109.5
O3—C6—C5	121.34 (12)	H15B—C15—H15C	109.5
C7—C6—C5	116.90 (12)

C2—O1—C1—C13	52.14 (11)	C3—C2—C8—C9	−27.1 (2)
C2—O1—C1—C5	−58.12 (11)	C4—C2—C8—C9	106.73 (16)
C1—O1—C2—C3	−178.08 (10)	C14—O4—C9—C8	−176.91 (12)
C1—O1—C2—C8	−51.22 (11)	C14—O4—C9—C10	4.67 (19)
C1—O1—C2—C4	58.56 (10)	C13—C8—C9—O4	−179.83 (11)
O1—C2—C4—O2	81.46 (11)	C2—C8—C9—O4	1.0 (2)
C3—C2—C4—O2	−38.70 (15)	C13—C8—C9—C10	−1.29 (19)
C8—C2—C4—O2	−174.15 (10)	C2—C8—C9—C10	179.56 (13)
O1—C2—C4—C5	−36.26 (11)	O4—C9—C10—C11	−179.33 (12)
C3—C2—C4—C5	−156.42 (11)	C8—C9—C10—C11	2.2 (2)
C8—C2—C4—C5	68.13 (12)	C9—C10—C11—C12	−0.4 (2)
O1—C1—C5—C6	−85.45 (12)	C15—O5—C12—C13	−176.80 (12)
C13—C1—C5—C6	168.38 (11)	C15—O5—C12—C11	2.9 (2)
O1—C1—C5—C4	33.82 (12)	C10—C11—C12—O5	177.95 (13)
C13—C1—C5—C4	−72.35 (12)	C10—C11—C12—C13	−2.4 (2)
O2—C4—C5—C6	5.64 (15)	C9—C8—C13—C12	−1.6 (2)
C2—C4—C5—C6	122.10 (11)	C2—C8—C13—C12	177.80 (12)
O2—C4—C5—C1	−114.69 (11)	C9—C8—C13—C1	−178.95 (11)
C2—C4—C5—C1	1.77 (12)	C2—C8—C13—C1	0.42 (13)
C1—C5—C6—O3	10.24 (18)	O5—C12—C13—C8	−176.91 (12)
C4—C5—C6—O3	−102.85 (14)	C11—C12—C13—C8	3.4 (2)
C1—C5—C6—C7	−166.79 (12)	O5—C12—C13—C1	−0.3 (2)
C4—C5—C6—C7	80.12 (15)	C11—C12—C13—C1	179.95 (13)
O1—C2—C8—C13	31.93 (12)	O1—C1—C13—C8	−33.15 (13)
C3—C2—C8—C13	153.61 (12)	C5—C1—C13—C8	73.48 (13)
C4—C2—C8—C13	−72.51 (12)	O1—C1—C13—C12	149.85 (14)
O1—C2—C8—C9	−148.83 (14)	C5—C1—C13—C12	−103.52 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3ⁱ	0.97 (3)	1.89 (2)	2.8295 (15)	162 (2)
C7—H7C···O3ⁱ	0.98	2.42	3.3936 (19)	173

Symmetry code: (i) −x+3/2, y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3ⁱ	0.97 (3)	1.89 (2)	2.8295 (15)	162 (2)
C7—H7C···O3ⁱ	0.98	2.42	3.3936 (19)	173

Symmetry code: (i) −x+3/2, y+1/2, z.

Acknowledgements

This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2012). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tranmer, G. K. & Tam, W. (2002). Org. Lett. 4, 4101–4104. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 70| Part 5| May 2014| Page o545

doi:10.1107/S1600536814007764

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-(3-Hy­dr­oxy-5,8-dimeth­­oxy-4-methyl-1,2,3,4-tetra­hydro-1,4-ep­­oxy­naphthalen-2-yl)ethan-1-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(3-Hydroxy-5,8-dimethoxy-4-methyl-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-2-yl)ethan-1-one