15584-52-8Relevant academic research and scientific papers
Preparation and testing of homocubyl amines as therapeutic NMDA receptor antagonists
Sklyarova, Anna S.,Rodionov, Vladimir N.,Parsons, Christopher G.,Quack, Guenter,Schreiner, Peter R.,Fokin, Andrey A.
, p. 360 - 366 (2013/03/29)
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
Rodionov,Sklyarova,Shamota,Schreiner,Fokin
experimental part, p. 1695 - 1702 (2012/03/12)
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.
Convenient preparative synthesis of pentacyclo[5.3.0.02,5.03,9.04,8]decane (C 2-Bishomocubane)
Sklyarova,Rodionov,Fokin
experimental part, p. 1633 - 1636 (2010/05/03)
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.
SYNTHESIS AND -CYCLOREVERSION OF CAGE KETONES
Yamashita, Yoshiro,Mukai, Toshio
, p. 1741 - 1744 (2007/10/02)
A series of pentacyclic cage ketones 2b-d having no substituent was synthesized by the photochemical -cycloaddition reaction of corresponding tricyclic dienones 1b-d.The cage ketones 2b-d underwent thermal -cycloreversion to give dienones 1b-d.The reactivities were dependent on the length of the bridge "X".
Carbonylation and Valence Isomerization of 1,3-Dihomocubane Derivatives by Chlorodicarbonylrhodium Dimer
Zlotogorski, Changa,Blum, Jochanan,Osawa, Eiji,Schwartz, Helmut,Hoehne, Gerhard
, p. 971 - 976 (2007/10/02)
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
Mehta, Goverdhan,Pandey, Paras N.,Usha, R.,Venkatesan, K.
, p. 177 - 185 (2007/10/02)
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.
Photochemical Formation of Strained Cage Compounds and their Acid-catalysed Reversion as a Preliminary Model for Light Energy Conversion
Hamada, Tatsuo,Iijima, Hideo,Yamamoto, Tohru,Numao, Naganori,Hirao, Ken-ichi,Yonemitsu, Osamu
, p. 696 - 697 (2007/10/02)
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.
