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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.

ABSTRACT: 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.

SUBMITTER: Bimoussa A

PROVIDER: S-EPMC3884344 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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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.

Bimoussa Abdoullah A Auhmani Aziz A Ait Itto My Youssef MY Daran Jean-Claude JC Auhmani Abdelwahed A

Acta crystallographica. Section E, Structure reports online 20131023 Pt 11

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. ...[more]

PMID: 24454120

Similar Datasets

(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)-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 ?-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.

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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,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)°.

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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.

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Crystal structure of (1S,3R,8R,9S,10R)-10-bromo-methyl-2,2-di-chloro-9,10-ep-oxy-3,7,7-tri-methyl-tri-cyclo-[6.4.0.0(1,3)]dodeca-ne.

Project description:The title compound, C16H23BrCl2O, was synthesized in three steps 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 two fused six- and seven-membered rings, each linked to a three-membered ring. The six-membered ring has a screw-boat conformation, whereas the seven-membered ring displays a twist-boat conformation. The absolute structure was established unambiguously from anomalous dispersion effects.

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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)°.

| S-EPMC3588943 | biostudies-literature

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.

| S-EPMC4571362 | 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-other

(1S,3R,8R,10R)-2,2-Di-bromo-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodecan-9-one.

Project description:The title compound, C16H24Br2O was synthesized by three steps from ?-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from essential oil of the Atlas cedar (Cedrus atlantica). The mol-ecule is built up from a seven-membered ring to which a six- and a three-membered ring are fused. The six-membered ring shows a chair conformation. One C atom in the seven-membered ring and two methyl groups attached to the ring are disordered over two sets of sites, with an occupancy ratio of 0.658?(7):0.342?(7).

| S-EPMC3885047 | biostudies-literature

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