15443-37-5

Usage

InChI:InChI=1/C10H10O/c11-10-7-3-1-2-4-5(3)9(10)8(4)6(2)7/h2-9H,1H2

Upstream product

• 5530-96-1 endo-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one 
• 13351-15-0 anti-Octahydro-1,2,4-metheno-1H-cyclobutapentalen-3-ol 
• 57293-86-4 ethylene ketal of pentacyclo[5.3.0.0(2,5).0(3,9).0(4,8)]decan-6-one 
• 105500-35-4 (1R,2S,6R,7S)-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one 
• 59189-81-0 C₁₂H₁₆O₂ 
• 94645-36-0 pentacyclo<5.3.0.0^2,6.0^3,10.0^4,8>decan-5-one-2-carboxylic acid 

Downstream Products

• 6707-86-4 Octahydro-1,2,4-metheno-1H-cyclobutapentalene 
• 62234-84-8 exo-2-hydroxy-9-cyanobrend-4-ene 3,5-dinitrobenzoate 

Relevant academic research and scientific papers

Convenient preparative synthesis of pentacyclo[5.3.0.02,5.03,9.04,8]decane (C 2-Bishomocubane)

By reaction of pentacyclo[5.3.0.02,5.03,9.04,8]decane-6,10-dione 6-ethyleneketal with lithium aluminum hydride the corresponding hydroxyketal was obtained whose hydroxy group was replaced by chlorine at boiling in CCl4 in the presence of a 15% molar excess of triphenylphosphine. 6-Ethyleneketal of pentacyclo-[5.3.0.02,5.03,9.04,8]decan-6-one obtained by dechlorination of the chloroketal in a system lithium-t-BuOH in THF was hydrolyzed to ketone by heating in 10% sulfuric acid in the presence of THF. The obtained ketone was reduced along Wolf-Kishner reaction to pentacyclo[5.3.0.02,5.03,9.04,8]decane.

Photochemical Formation of Strained Cage Compounds and their Acid-catalysed Reversion as a Preliminary Model for Light Energy Conversion

On irradiation, some Diels-Alder adducts derived from cyclic dienes and dienones gave, quantitatively, strained pentacyclic C12, C11, and C10 cage compounds, which rapidly and completely reverted to the starting compounds with the evolution of heat (18.0-23.5 kcal/mol) when treated with an acid; the C11 system was found to be the most promising for the reversible storage of light energy.

Preparation and testing of homocubyl amines as therapeutic NMDA receptor antagonists

Computational modeling demonstrates that the van-der-Waals surfaces of homocubyl amines are similar to that of the neuroprotector Memantine . Utilizing readily available precursors we report the preparation of a series of homological cubylamines, namely pentacyclo[6.3.0. 02,6.03,10.05,9]undecyl-4-amine (trishomocubyl-4-amine, 2), pentacyclo[5.3.0.02,5.0 3,9.04,8]decyl-10-amine (bishomocubyl-10-amine, 3), pentacyclo[4.3.0.02,5.03,8.04,7]nonyl-9-amine (homocubyl-9-amine, 4), and pentacyclo[4.2.0.02,5.0 3,8.04,7]octyl-1-amine (cubylamine, 5). The hydrochlorides of amines 2-5 show pronounced affinity for the (+)MK-801 channel binding site, and it seems likely that these compounds would act as very fast voltage-dependent NMDA receptor antagonists.

Selective reductive dimerization of homocubane series oximes

The mixture of di- and monoethylene ketals obtained by the reaction of 1,9-dibromopentacyc lo[5.4.0.02,6.03,10.0 5,9]-undeca-8,11-dione followed by hydrolysis and ring contraction by Faworsky method was converted into a mixture of ethylene ketals of 7-bromopentacyclo[5.3.0.02,5.03,9.04,8]decan-6- one-4- and 5-bromopentacyclo[5.3.0.02,5.03,9.0 4,8]decan-6-one-8-carboxylic acid where the carboxy group was replaced by bromine along the procedure of Hunsdiecker-Borodine-Cristol. 6-Ethylene ketal of the pentacyclo[5.3.0.02,5.03,9.0 4,8] decan-6-one obtained by the debromination of ethylene ketals of 4,7- and 5,8-dibromopentacyclo[5.3.0.02,5.03,9.0 4,8] decan-6-one was hydrolyzed to ketone whose oxime was selectively reduced on a platinum catalyst into the di-6-pentacyclo[5.3.0.0 2,5.03,9.04,8]decylamine. The reaction of reductive dimerization was also characteristic of pentacyclo[4.3.0.0 2,5.03,8.04,7]-nonan-9-one and pentacyclo[6.3.0.02,6.03,10.05,9]undecan-4-one oximes, whereas the composition of the reduction products of pentacyclo[5.4.0.02,6.03,10.05,9]undecan-8-one oxime depended on the amount of the catalyst.

A stereo- and enantioselective approach to clavulones from tricyclodecadienone using flash vacuum thermolysis

The stereo- and enantioselective synthesis of clavulones 6 and their analogues 48 is described. γ-Hydroxycyclopentenones (-)-13 and 44, which are key intermediates in this approach, are obtained from enantiopure endo-tricyclo[5.2.1.02,6]decadienones (+)-14 and (+)-20 in 6 and 8 steps, respectively. Crucial steps are the reductive epoxy ring opening in compounds (+)-25 and 39 to give the corresponding diols (+)-27 and 40, and the thermal cycloreversion of tricyclodecenones (+)-27 and 41, using the technique of flash vacuum thermolysis (FVT). The synthesis of enantiopure (-)-13 represents a formal total synthesis of clavulones 6. The synthesis of vlavulone analogues (-)-48E and (-)-48Z (X = CH2OH) is completed by condensation of 44 with aldehyde 45 followed by elimination of water and removal of the protective THP-group.

Carbonylation and Valence Isomerization of 1,3-Dihomocubane Derivatives by Chlorodicarbonylrhodium Dimer

1,3-Dihomocubane and several analogous cage compounds react with Rh2(CO)4Cl2 to give dinuclear acyl-rhodium complexes.These complexes are transformed into dicyclopentadiene and/or D3-trihomocubanone derivatives either upon heating or by treatment with triphenylphosphine. 1,3-Ethanomethanocubane reacts analogously.The kinetics of these metal-induced transformations follow the second-order rate law.A linear relationship exists between the constants and the calculated strain energies of the starting cage compounds.

1,3-Bishomocubane -> Brendane Rearrangement: Molecular Structure and Reactions of exo-2-Methanesulphonoxy-endo-9-cyanobrend-4-ene

A novel one-step rearrangement of pentacyclo2,5.03,9.04,8>decan-6-one (1,3-bishomocubanone, 1) to exo-2-methanesulphonoxy-9-cyanobrend-4-ene (2a) in the presence of sodium azide in methanesulphonic acid is reported.Structure of 2a is deduced through its interesting transformations to 2-cyanodeltacyclene (13) and 2-cyanonorsnoutane (15).When the rearrangement of 1 is carried out with sodium azide in trifluoroacetic acid, 3-substituted tetracyclo2,9.04,8>nonane is also obtained in addition to brend-4-ene derivative (2b).Plausible mechanism for the formation of 2a from 1 has been proposed.Single crystal X-ray crystallographic studies on 3,5-dinitrobenzoate of exo-2-hydroxy-9-cyanobrend-4-ene (2c) have been carried out to provide unambiguous proof for the structure, and its molecular structure is discussed in detail.