Bicyclo[3.3.1]nonane-2,9-dione derivatives

Conclusions Bicyclo[3.3.1]nonane-2,9-dione derivatives, containing substituents in the 7 position, were synthesized by the condensation of the morpholine enamines of 4-substituted cyclohexanones with acryloyl chloride.Translated from Izvestiya Akadeinii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1408–1410, June, 1976.     

Acid-catalysed acylations of bicyclo[3.3.1]nonan-2,6-diones: A novel preparation of the adamantane skeleton

The acid-catalysed acylations of bicyclo[3.3.1]nonan-2,6-dione 1 and its 9-thia-2 and 9-oxa-3 analogues with Ac₂O are described. At high acidity, C-acylation is favoured over O-acylation and for 1 and 2 intramolecular aldol condensation occurs with the formation of adamantanes 18 and 19 and 2-thiaadamantanes 15 and 16. These results are compared with alternative acylations of 2 using 2-acetoxypropene, (PhCO)₂O and acid halides.     

Synthesis and Chemical Transformations of 7-Hydroxybicyclo[3.3.1]nonane-3-carbohydrazide

Russian Journal of Organic Chemistry - The reaction of 4-oxahomoadamantan-5-one with hydrazine gave (3-exo,7-endo)-7-hydroxybicyclo[3.3.1]nonane-3-carbohydrazide. The latter was reacted with...     

Reaction of methyl 4,9-dioxobicyclo[3.3.1]nonane-2-carboxylate with hydrazine hydrate

Vilnius University, Vilnius 2734. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 416–417, March, 1995. Original article submitted January 20, 1995.     

Molecular structure of 3,7-dimethyl-9-thia-3,7-diazabicyclo[3.3.1]nonane-9,9-dioxide

By a single crystal X-ray diffraction study the molecular structure of 3,7-dimethyl-9-thia-3,7-diazabicyclo[3.3.1]nonane-9,9-dioxide having a chair-chair conformation with a diequatorial arrangement of methyl groups at nitrogen atoms is determined. Compound 1 C₈H₁₆N₂O₂S crystallizes in the space group Pnma with the following cell parameters: a = 11.0262(3) Å, b = 14.4490(3) Å, c = 6.1780(3) Å.     

Revised structure of diastereomeric 3,8-di-t-butylspiro[4,4]nonane-1,6-diones

The recently assigned diastereomeric configuration of 3,8-di-t-butylspiro[4.4]nonane-1,6-dione has been revised based on the X-ray analysis.     

Bicyclo[3.3.1]nonane and its derivatives—IV : Reactions of some carbonyl derivatives of bicyclo[3.3.1]nonane with diazomethane

The reaction of bicyclo[3.3.1]nonane-2,6-dione with diazomethane in situ does not lead to the homologous bicyclo[4.3.1]decane-2,7-dione, but mainly to tricyclo[4.4.0.0^2,9]decan-9-ol-5-one. The structure of the latter was confirmed by the proton NMR spectra measured with an addition of Eu(DPM)₃, A mixture of tricyclo[4,4.0.0^2,9]decan-9-ol-5-one and bicyclo[4.3.1]decane-2,7-dione results when solutions of diazomethane are used. The reaction of bicyclo[3.3.1]nonane-2,6-dione monoethyleneacetal with diazomethane in situ yields predominantly bicyclo[4.3.1]decane-2,7-dione. Under the same conditions bicyclo[3.3.1]nonan-2-one gives with diazomethane in situ only bicyclo[4.3.1]decan-2-one.     

Four New Lignans with a Bicyclo[3.3.1]nonadienemethanol Skeleton from Cunninghamia lanceolata

Four unique bicyclo[3.3.1]nonadienemethanol lignans, designated lanceolatanins A ( 1 ), B ( 2 ), C ( 3 ), and D ( 4 ), along with one previously known compound, isolariciresinol ( 5 ), were isolated from the MeOH extracts of the heartwood of Cunninghamia lanceolata. Their structures were elucidated by application of various spectroscopic methods, including 1D‐ and 2D‐NMR techniques, to their acetylated derivatives 1a, 2a, 3a , and 4a . Their possible biosynthetic formations are also discussed.