1-(7-Isopropyl-2,5-dimethyl-8-nitronaphthalen-1-yl)ethanone

Abstract

The title compound, C17H19NO3, was synthesized in three steps from a mixture of α-, β- and γ-himachalene, which was isolated from an essential oil of the Atlas cedar (Cedrus atlantica). The dihedral angle between the two rings of the naphthalene moiety is 2.54 (5)°. The nitro group and the acetyl group lie almost normal to the mean plane of the naphthalene moiety, making dihedral angles of 80.29 (13) and 83.01 (15)°, respectively, and are inclined to one another by 13.23 (19)°. There is an intramolecular C—H...O hydrogen bond present involving a nitro O atom and the H atom of the methine C atom of the isopropyl group, forming anS(6) ring motif. In the crystal, molecules are linked by pairs of C—H...π interactions, forming inversion dimers. There are no other significant intermolecular interactions present.

1-(2-Isopropyl-4,7-dimethyl-3-nitronaphthalen-1-yl)ethanone

“…This oil is made up mainly (75%) of bicyclics sesquiterpene hydrocarbons, among which are found the compounds -,and -himachalene (El Haib et al, 2011;Loubidi et al, 2014). The reactivity of these sesquiterpenes and their derivatives have been studied extensively by our team in order to prepare new products having biological proprieties (El Haib et al, 2011;Zaki et al, 2014;Benharref et al, 2016Benharref et al, ,2017Ait Elhad et al, 2017). Indeed, these compounds have been tested, using the food poisoning technique, for their potential antifungal activity against the phytopathogen botrytis cinera (Daoubi et al, 2004).…”

“…3 g (15 mmol) of 1,6-dimethyl-4-iso-propylenaphtalene (Benharref et al, 2016;Ait Elhad et al, 2017) dissolved in 50 ml of dichloromethane with 1.4 g (15 mmol) of aluminium chloride (AlCl 3 ) and one equivalent of acetyl chloride (CH 3 COCl) was stirred at 273 K for 2 h. After addition of 40 ml water, the reaction mixture was extracted (3 Â 20 ml) with dichloromethane. The organic phases were combined, dried over sodium sulfate and then concentrated in vacuo.…”

6-Methyl-1-(nitromethyl)-4-(propan-2-yl)naphthalene

“…The bicyclic sesquiterpenes -,and -himachalene are the main constituents of the essential oil of the Atlas cedar (Cedrus Atlantica) (El Haib et al, 2011;Loubidi et al, 2014). The reactivity of these sesquiterpenes and derivatives has been studied extensively by our team in order to prepare new products having biological proprieties (Zaki et al, 2014;Benharref et al, 2016;Ait Elhad et al, 2017). Indeed, these compounds were tested, using the food-poisoning technique, for their potential antifungal activity against the phytopathogen Botrytis cinerea (Daoubi et al, 2004).…”