15291-18-6Relevant articles and documents
The 9-homocubyl cation
Spitz, Urs P.
, p. 10174 - 10182 (1993)
The solvolysis of 9-homocubyl triflate-9-d (8-9-d), the deamination of 9-homocubylammonium chloride-9-d (15-9-d), and most likely also the fluorodeiodination of 9-homocubyl iodide-9-d (13-9-d) take place in a highly stereoselective manner. Both deamination and solvolysis products have the deuterium label scrambled only over one face of the homocubyl cage (syn to the substituent) and are formed with retention at C(9). In more nucleophilic media, the solvolysis of 8-9-d loses the stereoselectivitiy due to partial SN2 substitution, and under nonionizing, very nucleophilic conditions, a pure SN2 displacement of the triflate takes place. NMR experiments show that the SN1 reaction of 8-9-d proceeds via repeated internal return of the triflate leaving group. A similar mechanism involving internal return in the deamination and fluorodeiodination reactions is unconvincing because of the low nucleophilicity (N2) or the instability (IF2-) of the corresponding leaving groups. The observed preservation of the steric information is best explained by a nonclassical ground-state structure, 1b, for the homocubyl cation which additionally undergoes rapid stereoselective automerizations. No evidence was found for a degenerate cation involving all nine homocubyl positions as had been proposed earlier.
Cargill,King
, p. 409 (1970)
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.
