19888-33-6Relevant articles and documents
Diethyl ether-boron trifluoride (1/1) induced transannular cyclization reaction of humulene 2,3-epoxide
Hayano, Kiyoharu,Shirahama, Haruhisa
, p. 459 - 464 (1996)
The treatment of (6E, 9E)-2,3-epoxy-3,7,11,11-tetramethylcycloundeca-6,9-diene with Et2O·BF3 produced four novel transannular cyclized compounds of (4E)-(1S*, 8S*, 9S*)-8-acetoxy-6,6,9-trimethyl-2-methylenebicyclo[7.2.0]undec-4-ene (13), (2Z, 4E)-(1S*, 8S*, 9S*)-8-acetoxy-2,6,6,9-tetramethylbicyclo[7.2.0]undeca-2,4-diene (14), (6E)-(1R*, 2R*, 3S*, 10R*)-3-acetoxy-2,5,5-trimethyl-9-methylenebicyclo[8.1.0]undec-6-ene (15), and (4E)-(1S*, 2S*, 8S*, 9S*)-2,8-diacetoxy-2,6,6,9-tetramethylbicyclo[7.2.0]undec-4-ene (16) together with three new acetates: (2E, 5E, 8E)-1-acetoxy-2, 6,10,10-tetramethylcycloundeca-2,5,8-triene, (1E, 6E)-3,9-diacetoxy-2,5,5,9-tetramethylcycloundeca-1,6-diene, and (4E, 7E)-1-acetoxy-3,3,7-trimethyl-11-methylenecycloundeca-4,7-diene. The configurations of the bicyclo[7.2.0]undecane skeletons (13, 14, and 16) and 15 maintained the shape of TC and CT conformers of the original epoxide, respectively.
Monoepoxidation of humulene 2,3-epoxide to humulene 2,3;6,7-diepoxides. Observation of the rotation of the double bond plane by 1H NMR spectral analysis and conformation
Hayano, Kiyoharu,Mochizuki, Katsura
, p. 387 - 393 (2007/10/03)
The reaction of (6E,9E)-humulene 2,3-epoxide (7) with m-CPBA produced two known humulene 2,3;6,7-diepoxides (8 and 9), and careful analysis of the 1H NMR of 7 at various temperatures suggested an equilibrium of four possible conformations, CT,
Rearrangement of humulene-8,9-epoxide
Bryson, Ian,Roberts, James S,Sattar, Abdul
, p. 201 - 204 (2007/10/02)
Rearrangement of humulene-8,9-epoxide with tin(IV) chloride leads to the formation of a bicyclic alcohol, the structure of which is related to a rearrangement product of humulene itself.