121 research outputs found
(±)-N-[4-Acetyl-5-methyl-5-(4-methylcyclohex-3-enyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide
The new title thiadiazole compound, C14H21N3O2S, was semi-synthesized starting from 1-(4-methylcyclohex-3-enyl)ethanone, a natural product isolated from Cedrus atlantica essential oil. The stereochemistry has been confirmed by single-crystal X-ray diffraction. The thiadiazoline ring is roughly planar, although it may be regarded as having a half-chair conformation. The cyclohexenyl ring has a half-chair conformation. The most interesting feature is the formation of a pseudo-ring formed by four molecules associated through N—H⋯O hydrogen bonds around a fourfold inversion axis, forming an R
4
4(28) motif
10α-Hydroxy-13-{[4-(4-methoxyphenyl)piperazin-1-yl]methyl}-4,9-dimethyl-3,8,15-trioxatetracyclo[10.3.0.02,4.07,9]pentadecan-14-one
The title compound, C26H36N2O6, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The molecule is built up from fused five- and ten-membered rings with two additional epoxy ring systems and a methoxyphenylpiperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hydroxy group forming the flap. The molecular conformation is determined by an O—H⋯N hydrogen bond between the hydroxy group and a piperazine N atom. The crystal structure is built up by weak C—H⋯O interactions
1-Isopropyl-4,7-dimethyl-2,8-dinitronaphthalene
The title compound, C15H16N2O4, was synthesized from a mixture of α-himachalene (2-methylene-6,6,9-trimethylbicyclo[5.4.O1,7]undec-8-ene) and β-himachalene (2,6,6,9-tetramethylbicyclo[5.4.01,7]undeca-1,8-diene) which were isolated from an oil of the Atlas cedar (Cedrus atlantica). The asymmetric unit contains two independent molecules. In each of the two molecules, two O atoms of one nitro group are disordered over two sets of sites with site-occupancy factors of 0.636 (5):0.364 (5) and 0.832 (5):0.168 (5). The crystal structure features weak C—H⋯O hydrogen bonds
12-{[4-(2-Fluorophenyl)piperazin-1-yl]methyl}-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
The title compound, C25H33FN2O4, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-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. The asymmetric unit contains two independent molecules. In each molecule, the ten-membered ring displays an approximative chair–chair conformation. Each of the piperazine rings adopts a perfect chair conformation, while both lactone rings show an envelope conformation, one with the C atom bearing the piperazin-1-ylmethyl group as the flap, the other with the junction C atom not attached to the ring O atom as the flap. The dihedral angles between the least-squares planes through the ten- and five-membered rings in the two molecules are similar [19.1 (3) and 16.2 (3)°]. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation. The crystal packing is stabilized by C—H⋯O hydrogen bonds
Crystal structure of (1S,2R,4R,9S,11S,-12R)-9α-hydroxy-4,8-dimethyl-12-[(thio-morpholin-4-yl)methyl]-3,14-dioxatri-cyclo[9.3.0.02,4]tetradec-7-en-13-one
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.Peer reviewedPublisher PD
12-Anilinomethyl-9α-hydroxy-4,8-dimethyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
The title compound, C21H27NO4, was synthesized from 9α-hydroxyparthenolide, which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The asymmetric unit contains two independent molecules. In each, the ten-membered ring displays an approximative chair-chair conformation. Each of the five-membered rings adopts a flattened envelope conformation, the C(H)—C—C(H) atoms representing the flap lie out of the mean plane through the remaining four atoms by 0.443 (2) and 0.553 (2) Å. The dihedral angle between the least-squares planes through the ten- and five-membered rings in the two molecules are similar [22.54 (17) and 23.39 (14)°]. In the crystal, molecules are linked by O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds
5,9-Dihydroxy-9-methyl-3,6-dimethylene-3a,4,5,6,6a,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-2(3H)-one
The title compound, C15H20O4, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-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. The seven-membered ring has a chair conformation, while the five-membered rings display twisted conformations. The dihedral angle between the seven-membered ring and the lactone ring is 21.69 (10)°. In the crystal, molecules are linked into chains propagating along the c axis by intermolecular O—H⋯O hydrogen bonds; an intramolecular O—H⋯O link also occurs
Methyl 2-(3a,8a-dimethyl-4-oxodecahydroazulen-6-yl)acrylate
The title compound, C16H24O3, was synthesized from ilicic acid, which was isolated from the aerial part of Inula viscosa (L) Aiton [or Dittrichia viscosa (L) Greuter]. The asymmetric unit contains two independent molecules, in each of which the seven-membered ring shows a chair conformation, whereas the five-membered ring presents disorder. In the two molecules, three C atoms in the five-membered ring are disordered over two positions with site-occupancy factors of 0.53/0.47 and 0.83/0.17. The dihedral angle between the two rings is different in the two molecules [31.7 (3) and 47.7 (7)°]. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen-bond interactions
2α,8α-Diacetoxy-cis-himachalane
The title compound, C19H32O4, was synthesized from γ-himachalene, wich was isolated from essential oils of Cedrus atlantica. The molecule is built up from two fused six- and seven-membered rings. The six-membered ring has a screw-boat conformation, whereas the seven-membered ring displays a half-chair conformation; the dihedral angle between the mean planes of the rings is 61.99 (6)°
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