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9-Hy-droxy-4,8-dimethyl-12-(piperidin-1-ylmeth-yl)-3,14-dioxatricyclo-[9.3.0.0]tetra-dec-7-en-13-one.

ABSTRACT: The title compound, C(20)H(31)NO(4), 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-membered ring display a chair conformation and the five-membered ring an envelope conformation with the C(H)-C-C(H) atom at the flap. The dihedral angle between the ten-membered ring and the lactone ring is 21.7?(4)°. The mol-ecular conformation is stabilized by an O-H?N hydrogen bond and the crystal structure is stabilized by weak inter-molecular C-H?O inter-actions.

SUBMITTER: Moumou M

PROVIDER: S-EPMC3201218 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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9-Hy-droxy-4,8-dimethyl-12-(piperidin-1-ylmeth-yl)-3,14-dioxatricyclo-[9.3.0.0]tetra-dec-7-en-13-one.

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

Acta crystallographica. Section E, Structure reports online 20110930 Pt 10

The title compound, C(20)H(31)NO(4), 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-membered ring display a chai ...[more]

PMID: 22058816

Similar Datasets

9-Hy-droxy-4,8-dimethyl-12-(pyrrolidin-1-ylmeth-yl)-3,14-dioxatricyclo-[9.3.0.0]tetra-dec-7-en-13-one.

Project description:The title compound, C(19)H(29)O(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 two fused five- and ten-membered rings with the pyrrolidin-1-ylmethyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and pyrrolidine rings display approximate chair-chair and twisted conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 18.01 (19)°. An intra-molecular O-H⋯N hydrogen bond occurs. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen-bonding inter-actions.

| S-EPMC3200593 | biostudies-literature

12-Anilinomethyl-9?-hy-droxy-4,8-dimethyl-3,14-dioxatricyclo-[9.3.0.0]tetra-dec-7-en-13-one.

Project description:The title compound, C(21)H(27)NO(4), was synthesized from 9?-hy-droxy-parthenolide, which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The asymmetric unit contains two independent mol-ecules. 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 mol-ecules are similar [22.54?(17) and 23.39?(14)°]. In the crystal, mol-ecules are linked by O-H?O, O-H?N and N-H?O hydrogen bonds.

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12-{[4-(2-Fluoro-phen-yl)piperazin-1-yl]-meth-yl}-9α-hy-droxy-4,8-dimethyl-3,14-dioxatricyclo-[9.3.0.0]tetra-dec-7-en-13-one.

Project description:The title compound, C(25)H(33)FN(2)O(4), 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 asymmetric unit contains two independent mol-ecules. In each mol-ecule, 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 mol-ecules are similar [19.1 (3) and 16.2 (3)°]. An intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecular conformation. The crystal packing is stabilized by C-H⋯O hydrogen bonds.

| S-EPMC3295510 | biostudies-literature

9?-Hy-droxy-12-{[4-(4-meth-oxy-phen-yl)piperazin-1-yl]meth-yl}-4,8-dimethyl-3,14-dioxatricyclo-[9.3.0.0]tetra-dec-7-en-13-one.

Project description:The title compound, C(26)H(36)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), wich 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 meth-oxy-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 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 0.343?(3)?Å. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 18.12?(14)°. An intra-molecular O-H?N hydrogen bond occurs. The crystal structure features weak C-H?O inter-actions.

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9?-Hy-droxy-12-{[4-(4-hy-droxy-phen-yl)piperazin-1-yl]meth-yl}-4,8-dimethyl-3,14-dioxatri-cyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one.

Project description:The title compound, C25H34N2O5, was synthesized from 9?-hy-droxy-parthenolide (9?-hy-droxy-4,8-dimethyl-12-methylen-3, 14-dioxa-tri-cyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which in turn was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule comprises a ten-membered ring fused to a five-membered ring with an additional ep-oxy ring system fused to the ten-membered ring. The five-membered ring also carries a 4-hy-droxy-phenyl-piperazin-1-ylmethyl 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. Two C atoms in the phenyl ring and the O atom of the hydroxyl group are disordered over two sites, with an occupancy ratio of 0.53?(5):0.47?(5). An intra-molecular O-H?N hydrogen-bond stabilizes the mol-ecular conformation. In the crystal, C-H?O hydrogen bonds link the mol-ecules into zigzag chains running along the a-axis direction.

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12-{[4-(4-Bromo-phen-yl)piperazin-1-yl]meth-yl}-9α-hy-droxy-4,8-dimethyl-3,14-dioxatri-cyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one.

Project description:The title compound, C25H33BrN2O4, was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tri-cyclo-[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 two fused five- and ten-membered rings with an additional ep-oxy ring system and a bromo-phenyl-piperazine group as a substituent. The ten-membered ring adopts an approximate chair-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. An intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecular conformation. The crystal packing features C-H⋯O hydrogen bonds, which link the mol-ecules into zigzag chains running along the b-axis direction.

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Crystal structure of (1S,2R,4R,9S,11S,12R)-9?-hy-droxy-4,8-dimethyl-12-[(thio-morpholin-4-yl)meth-yl]-3,14-dioxatri-cyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one.

Project description:The title compound, C19H29NO4S, was synthesised from 9?-hy-droxy-parthenolide (9?-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatri-cyclo-[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 the plant Anvillea radiata. The mol-ecule is built up from two fused five- and ten-membered rings, with an additional ep-oxy ring system and a thio-morpholine group as a substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the thio-morpholine ring displays a chair conformation and the five-membered ring has an envelope conformation, with the C atom closest to the hy-droxy group forming the flap. An intra-molecular O-H?N hydrogen bond closes an S(8) ring. The crystal structure features weak C-H?O hydrogen-bonding inter-actions, which link the mol-ecules into [010] chains.

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(E)-1-(3-Hy-droxy-phen-yl)-3-[4-(tetra-dec-yl-oxy)phen-yl]prop-2-en-1-one.

Project description:In the title compound, C(29)H(40)O(3), the enone moiety adopts an s-cis conformation. The dihedral angle between the benzene rings is 4.33?(5)° The least-squares mean line through the tetra-decyl side chain forms a dihedral angle of 83.99?(7)° with the normal to the attached benzene ring. In the crystal, O-H?O and C-H?O hydrogen bonds involving the keto and the hy-droxy O atoms form ribbons along [-41-1]. The crystal structure also features C-H?? inter-actions.

| S-EPMC3470259 | biostudies-literature

3-Hy-droxy-1-(4-meth-oxy-benz-yl)piperidin-2-one.

Project description:The title compound, C13H17NO3, adopts a conformation in which the aromatic ring and the mean plane of the piperidine ring are almost perpendicular to each other [dihedral angle = 79.25?(6)°]. The presence of the carbonyl group alters the conformation of the piperidine ring from a chair to a twisted half-chair conformation. In the crystal, pairs of strong O-H?O hydrogen bonds link the mol-ecules into inversion dimers. Weak C-H?O inter-actions extend the hydrogen-bonding network into three dimensions.

| S-EPMC3588348 | biostudies-literature

4-{[4-(Hy-droxy-meth-yl)piperidin-1-yl]meth-yl}phenol.

Project description:In the title compound, C(13)H(19)NO(2), the piperidine ring has a chair conformation with the exocyclic N-C bond in an equatorial position. In the crystal, mol-ecules are linked head-to-tail by phenol O-H⋯O hydrogen bonds to hy-droxy-methyl-ene O-atom acceptors, forming chains which extend along [100]. These chains form two-dimensional networks lying parallel to (101) through cyclic hydrogen-bonding associations [graph set R(4) (4)(30)], involving hy-droxy O-H donors and piperidine N-atom acceptors.

| S-EPMC3394056 | biostudies-literature

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