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10?-Hy-droxy-4,9-dimethyl-13-(pipyridin-1-ylmethyl)-3,8,15-trioxatetra-cyclo-[10.3.0.0.0]tetra-decan-14-one.

ABSTRACT: The title compound, C(20)H(31)NO(5), was synthesized from 9?-hy-droxy-parthenolide (9?-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo-[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 the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the six- and five-membered rings display chair and envelope conformations, respectively. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 20.8?(3)°. An intra-molecular O-H?N hydrogen-bond occurs. The crystal structure is stabilized by weak inter-molecular C-H?O hydrogen bonds.

SUBMITTER: Moumou M

PROVIDER: S-EPMC3247403 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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10α-Hy-droxy-4,9-dimethyl-13-(pipyridin-1-ylmethyl)-3,8,15-trioxatetra-cyclo-[10.3.0.0.0]tetra-decan-14-one.

Moumou Mohamed M Benharref Ahmed A Oudahmane Abdelghani A Elhakmaoui Ahmed A Berraho Moha M

Acta crystallographica. Section E, Structure reports online 20111022 Pt 11

The title compound, C(20)H(31)NO(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo-[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 the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the six- and five-membered rings d ...[more]

PMID: 22220021

Similar Datasets

10?-Hy-droxy-4,9-dimethyl-13-(morph-o-lin-4-ylmeth-yl)-3,8,15-trioxatetra-cyclo-[10.3.0.0.0]penta-decan-14-one.

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10?-Hy-droxy-4,9-dimethyl-13-[(4-phenyl-piperazin-1-yl)meth-yl]-3,8,15-trioxatetra-cyclo-[10.3.0.0.0]tetra-decan-14-one.

Project description:The title compound, C(25)H(34)N(2)O(5), was synthesized from 9?-hy-droxy-parthenolide (9?-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 contains a fused five- and ten-membered ring system. The ten-membered ring adopts an approximate chair-chair conformation, while the five-membered ring is in an envelope conformation, with the C atom closest to the hy-droxy group forming the flap. The piperazine ring is in a chair conformation. In the crystal, O-H?O hydrogen bonds connect mol-ecules into chains along [100]. Weak inter-molecular C-H?O hydrogen bonds are also present.

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10α-Hy-droxy-13-{[4-(2-hy-droxy-phen-yl)piperazin-1-yl]meth-yl}-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(34)N(2)O(6), 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 ten-membered ring adopts an approximate chair-chair conformation, while the piperazine ring displays a near regular chair conformation and the five-membered ring an envelope conformation with the C atom closest to the hy-droxy group forming the flap. The mol-ecular conformation is stabilized by an O-H⋯N hydrogen bond, which generates an S(7) loop, and the crystal structure features weak C-H⋯O inter-actions.

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10?-Hy-droxy-4,9-dimethyl-13-[(pyrrol-idin-1-yl)meth-yl]-3,8,15-trioxatetra-cyclo-[10.3.0.0.0]penta-decan-14-one.

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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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3-Hy-droxy-2-[(2-hy-droxy-4,4-dimethyl-6-oxocyclo-hex-1-en-1-yl)(3-nitro-phen-yl)meth-yl]-5,5-dimethyl-cyclo-hex-2-en-1-one.

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Dimethyl-ammonium 4-hy-droxy-benzoate.

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