Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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

ABSTRACT: 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)°.

SUBMITTER: Oukhrib A

PROVIDER: S-EPMC3588943 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

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

Oukhrib Abdelouahd A Benharref Ahmed A Saadi Mohamed M El Ammari Lahcen L Berraho Moha M

Acta crystallographica. Section E, Structure reports online 20121114 Pt 12

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, ...[more]

PMID: 23476179

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)-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

(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)-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)°.

| S-EPMC3588986 | 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

(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,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 β-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

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 β-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

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

Project description:The absolute configuration of the title compound, C16H24O, has been deduced from the chemical pathway. The six-membered ring has a roughly half-chair conformation with the quaternary C atom as the flap. The seven-membered ring displays a chair conformation. In the crystal, there is a weak C-H⋯O hydrogen bond between the methyl-ene group of the cyclo-propane ring and the carbonyl group of a screw-axis-related mol-ecule, which builds up a zigzag-like chain along the b-axis direction.

| S-EPMC3914107 | 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

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data