Methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate

Abstract

In the title compound, C21H18O5, the dihedral angle between the naphthalene ring system and the benzene ring is 86.65 (6)°. The bridging carbonyl C—C(=O)—C plane makes dihedral angles of 83.57 (7) and 20.21 (8)°, respectively, with the naphthalene ring system and the benzene ring. The ester O—C=O plane and the benzene ring are almost coplanar, making a dihedral angle of 3.81 (18)°. The two meth­oxy groups lie essentially in the naphthalene ring plane [C—O—C—C torsion angles = 2.1 (2) and −1.44 (19)°]. In the crystal structure, a centrosymmetric dimer is formed through C—H⋯O bonds connecting the 7-meth­oxy group and the carbonyl O atom of the ester group. The dimers are further linked by C—H⋯O hydrogen bonds between the methoxy­carbonyl group and the bridging carbonyl O atom.

(3,6-Dimethoxy-2-naphthyl)(4-fluorobenzoyl)methanone

“…Recently, we reported the structures of 1,8-diaroyl-2,7-dimethoxynaphthalenes, i. e., 1,8-bis(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Nakaema et al, 2007), bis(4-bromobenzoyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe et al, 2010a). In addition, the crystal structural analysis of 1-aroyl-2,7-dimethoxynaphthalenes, i. e., methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate (Hijikata et al, 2010) and 1-(4-nitorobenzoyl)-2,7-dimethoxynaphthalene (Watanabe et al 2010b), also has revealed essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes.…”

“…For general background to the regioselective formation of peri-aroylnaphthalene compounds, see: Okamoto & Yonezawa (2009). For related structures, see: Hijikata et al (2010); Mitsui et al (2008); Nakaema et al (2007Nakaema et al ( , 2008; Watanabe et al (2010a,b).…”

1-[(4-Chlorophenyl)(phenylimino)methyl]-7-methoxy-2-naphthol–1,4-diazabicyclo[2.2.2]octane (2/1)

“…For our study of the electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene and peri-aroylnaphthalene compounds, see: Okamoto & Yonezawa (2009). For related structures, see: Hijikata et al (2010); ; Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008); Watanabe, Nakaema, Muto et al (2010); Watanabe, Nakaema, Nishijima et al (2010). Table 1 Hydrogen-bond geometry (Å , ).…”

“…The aroyl groups in these compounds are bonded almost perpendicularly to the naphthalene rings at the 1,8-positions but the benzene ring moieties of the aroyl groups tilt slightly toward the exo sides of the naphthalene rings. Moreover, the X-ray crystal structural analyses of 1-(4-substituted benzoylated)naphthalenes, i.e., 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui, Nakaema, Okamoto & Yonezawa, 2008), 1-(4-nitrobenzoyl)-2,7-dimethoxynaphthalene (Watanabe, Nakaema, Nishijima et al, 2010) and methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate (Hijikata et al, 2010), have also revealed essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes. Contrarily, the benzene ring of (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone ) is bonded to the naphthalene ring with nearly coplanar configuration in the opposite direction against the 2-hydroxy group.…”