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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.

ABSTRACT: 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)°.

SUBMITTER: Oukhrib A

PROVIDER: S-EPMC3588986 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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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.

Oukhrib Abdelouahd A Benharref Ahmed A Saadi Mohamed M Daran Jean-Claude JC Berraho Moha M

Acta crystallographica. Section E, Structure reports online 20121124 Pt 12

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, whe ...[more]

PMID: 23476222

Similar Datasets

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

Project description:The title compound, C(16)H(24)Br(2), 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 two fused six- and seven-membered rings and an additional three-membered ring from the reaction of β-himachalene with dibromo-carbene. The six-membered ring shows a screw-boat conformation, whereas the seven-membered ring displays a boat conformation; the dihedral angle between the mean planes through the rings is 57.9 (4)°. The absolute structure was established unambiguously from anomalous dispersion effects.

| S-EPMC3414955 | biostudies-literature

(1S,3R,8R,11S)-11-Bromo-10-bromo-methyl-2,2-di-chloro-3,7,7-tri-methyl-tricyclo-[6.4.0.0(1,3)]dodec-9-ene.

Project description:The title compound, C16H22Br2Cl2, was synthesized from β-him-achalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-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 appended three-membered ring. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a chair conformation. The dihedral angle between the two best plane through each ring is 59.5 (2)°. No specific inter-molecular inter-actions were discerned in the crystal packing.

| S-EPMC3793778 | biostudies-literature

(1S,3R,8R)-9-(1-Amino-ethyl-idene)-2,2-dichloro-3,7,7-trimethyl-tricyclo-[6.4.0.0]undecan-10-one.

Project description:The title compound, C(16)H(23)Cl(2)NO, was synthesised 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 contains a seven membered ring, which is fused to a five- and a three-membered ring. The five-membered ring has a twisted conformation, whereas the seven-membered ring displays a chair conformation. The dihedral angle between the five- and seven-membered rings is 45.26 (9)°. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, mol-ecules are linked into chains propagating along the b axis by inter-molecular N-H⋯O hydrogen bonds; an intramolecular N-H⋯O link also occurs.

| S-EPMC3052109 | biostudies-literature

(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)°.

| S-EPMC3588943 | biostudies-literature

Absolute configuration of (1S,3R,8R)-10-bromo-methyl-2,2-di-chloro-3,7,7-tri-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-ene.

Project description:The absolute configuration of the title compound, C16H23BrCl2, has been deduced from the chemical pathway and fully confirmed by refinement of the Flack and Hooft parameters. The six-membered ring adopts a half-chair conformation, whereas the seven-membered ring is a twisted chair. The mol-ecular packing within the crystal is stabilized only by van der Waals inter-actions.

| S-EPMC3884344 | biostudies-literature

(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.

| S-EPMC3052100 | biostudies-literature

(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.

Project description:The title compound, C16H24Br2O, 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 contains fused six- and seven-membered rings, each linked to a three-membered ring. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a chair conformation. The dihedral angle between the mean planes through the six- and seven-membered rings is 39.55 (12)°. The two three-membered rings, linked to the six- and seven-membered rings, are nearly perpendicular to the six-membered ring, making dihedral angles of 78.6 (2) and 80.5 (2)°, respectively. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, each mol-ecule is linked to its symmetry-equivalent partner by C-H⋯O hydrogen bonds, forming zigzag chains parallel to [100].

| S-EPMC3629578 | biostudies-literature

(1S,3R,8R)-2,2-Di-chloro-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-en-11-one.

Project description:The title compound, C16H22Cl2O, was synthesized from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-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 arising from the reaction of himachalene with di-chloro-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 59.65 (14)°.

| S-EPMC3684918 | biostudies-literature

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

Project description:The title compound, C16H24Cl2O, was synthesized by treating (1S,3R,8S,9R,10S)-2,2-di-chloro-3,7,7,10-tetra-methyl-9,10-ep-oxy-tri-cyclo-[6.4.0.0(1,3)]dodecane with a concentrated solution of hydro-bromic acid. It is built up from three fused rings: a cyclo-heptane ring, a cyclo-hexyl ring bearing alkene and hy-droxy substituents, and a cyclo-propane ring bearing two chlorine atoms. The asymmetric unit contains two mol-ecules linked by an O-H⋯O hydrogen bond. In the crystal, further O-H⋯O hydrogen bonds build up an R 4 (4)(8) cyclic tetra-mer. One of the mol-ecules presents disorder that affects the seven-membered ring. In both mol-ecules, the six-membered rings display a chair conformation, whereas the seven-membered rings display conformations inter-mediate between boat and twist-boat for the non-disordered mol-ecule and either a chair or boat and twist-boat for the disordered mol-ecule owing to the disorder. The absolute configuration for both mol-ecules is 1S,3R,8R,9R and was deduced from the chemical pathway and further confirmed by the X-ray structural analysis.

| S-EPMC4971863 | biostudies-literature

(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 β-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)°].

| S-EPMC3009205 | biostudies-literature

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