9α-Hydroxy-4,8-dimethyl-3′-phenyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one-12-spiro-5′-isoxazole monohydrate

Fatima Outahar,Mohamed Saadi,El Mostapha Rakib,Abdellah Hannioui,Lahcen El Ammari,Mohamed Akssira

doi:10.1107/s2414314619014081

Fatima Outahar, Mohamed Saadi + Show 4 more

Open Access

https://doi.org/10.1107/s2414314619014081

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Abstract

In the title compound, C22H25NO5·H2O, the ten-membered ring displays an approximate chair–chair conformation, whereas the five-membered furan ring has an envelope conformation, with the C atom of the methine group adjacent to the spiro C atom as the flap. The isoxazole ring is almost planar and its plane is slightly inclined to the plane of the attached phenyl ring. The mean plane of the furan ring is nearly perpendicular to that of the isoxazole ring, as indicated by the dihedral angle between them of 89.39 (12)°. In the crystal, the organic molecules are linked into [010] chains by O—H...O hydrogen bonds. The water molecule forms O—H...O and O—H...N hydrogen bonds and a weak C—H...O interaction is also observed. Together, these lead to a three-dimensional network.

Highlights

In the title compound, C22H25NO5ÁH2O, the ten-membered ring displays an approximate chair–chair conformation, whereas the five-membered furan ring has an envelope conformation, with the C atom of the methine group adjacent to the spiro C atom as the flap
The organic molecules are linked into [010] chains by O—HÁ Á ÁO hydrogen bonds
The title compound was synthesized from 9-hydroxyparthenolide (9-hydroxy-4,8dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata (Quezel & Santa, 1963; Ozenda, 1958)

Summary

Structure description

The title compound was synthesized from 9-hydroxyparthenolide (9-hydroxy-4,8dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata (Quezel & Santa, 1963; Ozenda, 1958). Our work lies within the framework of the evaluation of medicinal plants and, in particular, Anvillea radiata. The main constituent of the chloroform extract of the aerial parts of this plant is 9-hydroxypartenolide (El Hassany et al, 2004). The reactivities of this sesquiterpene lactone and its derivatives have been the subject of several studies

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