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(1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy-droxy-3,7-dimethyl-11-methyl-idene-13-oxabicyclo-[8.3.0]tridec-6-en-12-one.

ABSTRACT: The title compound, C(15)H(21)ClO(4), was synthesized from 9?-hy-droxy-parthenolide (9?-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from fused five- and ten-membered rings. The five-membered lactone ring has an envelope conformation with the flap atom, C(H)-C-C(H), displaced by 0.2325?(15)?Å from the mean plane through the remaining four atoms, whereas the ten-membered ring displays an approximate chair-chair conformation. The dihedral angle between the two rings is 66.4?(2)°. In the crystal, mol-ecules are linked into chains propagating along the a axis by O-H?O hydrogen bonds.

SUBMITTER: Moumou M

PROVIDER: S-EPMC3247566 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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(1S,2R,3R,8R,10S)-3-Chloro-2,8-dihy-droxy-3,7-dimethyl-11-methyl-idene-13-oxabicyclo-[8.3.0]tridec-6-en-12-one.

Moumou Mohamed M Benharref Ahmed A Daran Jean-Claude JC Elhakmaoui Ahmed A Akssira Mohamed M Berraho Moha M

Acta crystallographica. Section E, Structure reports online 20111005 Pt 11

The title compound, C(15)H(21)ClO(4), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from fused five- and ten-membered rings. The five-membered lactone ring has an envelope conformation with the flap atom, C(H)-C-C(H), displaced by 0.2325 (15) Å from the mean plane through the remaining fou ...[more]

PMID: 22219871

Similar Datasets

(1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro-phen-yl)piperazin-1-yl]meth-yl}-10-hy-droxy-4,9-dimethyl-3,8,15-trioxatetra-cyclo-[10.3.0.0(2,4).0(7,9)]penta-decan-14-one.

Project description:The title compound, C(25)H(33)ClN(2)O(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from fused five- and ten-membered rings with two additional ep-oxy ring systems and a chloro-phenyl-piperazine 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 hy-droxy group forming the flap. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond between the hy-droxy group and a piperazine N atom. The crystal structure is stabilized by weak C-H⋯O inter-actions.

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Crystal structure of (1S,3R,8R,10S)-2,2-di-chloro-10-hy-droxy-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodecan-9-one.

Project description:The asymmetric unit of the title compound, C16H24Cl2O2, contains two independent mol-ecules (A and B) which are built from three fused rings, viz. a seven-membered heptane ring, a six-membered cyclo-hexyl ring bearing a ketone and an alcohol group, and a cyclo-propane ring bearing two Cl atoms. In the crystal, the two mol-ecules are linked via two O-H?O hydrogen bonds, forming an A-B dimer with an R 2 (2)(10) ring motif. The A mol-ecules of these dimers are linked via a C-H?O hydrogen bond, forming chains propagating along the a-axis direction. Both mol-ecules have the same absolute configuration, i.e. 1S,3R,8R,10S, which is based on the synthetic pathway and further confirmed by resonant scattering [Flack parameter = 0.03?(5)].

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(1S,3R,8R,9R,10S)-2,2-Dibromo-3,7,7,10-tetra-methyl-9β,10β-ep-oxy-3,7,7,10-tetra-methyl-tricyclo-[6.4.0.0(1,3)]dodeca-ne.

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Crystal structure of (1S,3R,8R,9R,10S)-2,4,6-tris-(2,2-di-chloro-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-yl)cyclo-triboroxane.

Project description:The title compound, C48H75B3Cl6O3, was synthesized in two steps from ?-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-hept-ene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule consists of an almost planar cyclo-triboroxane ring [maximum deviation = 0.036?(2)?Å] linked to three identical fused ring systems with different conformations. Each of the three attached ring systems is built up from a seven-membered ring to which a six- and a three-membered ring are fused. The three six-membered rings have a twist-boat conformation, whereas the seven-membered rings display boat, chair and twist-boat conformations. The dihedral angles between the central boroxane ring and the mean planes of the attached six-membered rings are 63.67?(18), 54.89?(2) and 56.57?(19)°. The crystal packing is governed only by van der Waals inter-actions.

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(1S,3R,8R)-2,2-Dibromo-3,7,7,10-tetra-methyl-tricyclo-[6.4.0.0(1,3)]dodec-9-ene.

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(1S,2R,8R)-2,2-Dichloro-3,7,7,10-tetra-methyltricyclo-[6.4.0.0]dodec-10-en-9-one.

Project description:The title compound, C(16)H(22)Cl(2)O, was synthesized from ?-himachalene, which was isolated from essential oil of the Atlas cedar (cedrus atlantica). The asymmetric unit contains two independent mol-ecules, in each of which the six-membered ring shows a half-chair conformation, whereas the seven-membered ring displays a boat conformation. The dihedral angle between the two rings is slightly different in the two mol-ecules [63.22?(13) and 61.81?(14)°].

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(1S,3R,8R)-2,2-Dibromo-3,7,7,10-tetra-methyltricyclo-[6.4.0.0(1,3)]dodec-9-en-11-one.

Project description:The title compound, C16H22Br2O, was synthesized from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule is built up from fused six- and seven-membered rings and an additional three-membered ring from the reaction of himachalene with dibromo-carbene. The six-membered ring has an envelope conformation, with the C atom belonging to the three-membered ring forming the flap, whereas the seven-membered ring displays a screw-boat conformation; the dihedral angle between the rings (all atoms) is 60.92 (16)°.

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(1S,3R,8R)-2,2-Dibromo-10-bromo-methyl-3,7,7-trimethyl-tricyclo-[6.4.0.0(1,3)]dodec-9-ene.

Project description:The title compound, C16H23Br3, was synthesized from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule is built up from fused six- and seven-membered rings and an additional three-membered ring from the reaction of himachalene with dibromo-carbene. The six-membered ring has an envelope conformation (the flap atom being the C atom shared with the three-membered ring, whereas the seven-membered ring displays a screw boat conformation; the dihedral angle between the rings (defined by the near coplanar atoms) is 56.5 (2)°.

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(1S,3R,8R,11S)-2,2-Dichloro-3,7,7,10-tetra-methyl-tricyclo-[6.4.0.0]dodec-9-en-11-ol.

Project description:The title compound, C(16)H(24)Cl(2)O, was synthesized from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from essential oil of the Atlas cedar (Cedrus atlantica). The two fused rings exhibit different conformations: the six-membered ring has a screw-boat conformation, while the seven-membered ring displays a boat conformation. The dihedral angle between the two rings is 56.56 (18)°. In the crystal, mol-ecules aggregate into supra-molecular chains along the c axis mediated by O-H⋯O hydrogen bonds.

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(1S,3R,8S,9R,10S)-2,2-Dichloro-3,7,7,10-tetra-methyl-9,10-ep-oxy-tricyclo-[6.4.0.0]dodeca-ne.

Project description:The title compound, C(16)H(24)Cl(2)O, was synthesized from ?-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from the essential oil of the Atlas cedar (cedrus atlantica). The mol-ecule forms an extended sheet of two fused rings which exhibit different conformations. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a chair conformation; the dihedral angle between the two rings is 38.2?(1)°.

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