(1S,3R,8R)-2,2-Dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0^1,3]dodec-9-en-11-one

Abstract

The title compound, C16H22Cl2O, was synthesized from β-himachalene (3,5,5,9-tetra­methyl-2,4a,5,6,7,8-hexa­hydro-1H-benzo­cyclo­heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol­ecule is built up from fused six- and seven-membered rings and an additional three-membered ring arising from the reaction of himachalene with di­chloro­carbene. 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)°.

N′-[(1S,3R,8R)-2,2-Dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodecan-11-yl]acetohydrazide

“…To a solution of an equimolecular quantity of (1S,3R,8R)-2,2dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0 1,3 ]dodecan-11one (Ourhriss et al, 2013) and thiosemicarbazide dissolved in ethanol, several drops of concentrated HCl were added. The reaction mixture was heated at reflux for 5 h and then evaporated under reduced pressure.…”

(1S,3R,8R)-2,2-Dichloro-3,7,7,10-tetramethyl-11-methylenetricyclo[6.4.0.01,3]dodec-9-ene

“…Thereafter, 6 g (20 mmol) of (1S,3R,8R)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.0 1 , 3 ] dodecan-11-one (Ourhriss et al, 2013) solubilized in 60 ml of ether were added dropwise. At the end of the addition, the mixture was stirred for 4 h at ambient temperature.…”