2958-72-7Relevant articles and documents
Baeyer-Villiger Oxidation of Pentacyclo2,6.03,10.05,9>undecane-8,11-dione
Surapaneni, C. Rao,Gilardi, Richard
, p. 2382 - 2385 (1986)
-
Barriers to Intramolecular Hydride Transfers in Some Polycyclic Hydroxyketones
Craze, Gabrielle-Anne,Watt, Ian
, p. 175 - 184 (1981)
The hydroxyketones (1) and (2) have been prepared from the Diels-Alder adducts of p-benzoquinone with cyclopentadiene and cyclohexa-1,3-diene.The boron trifluoride-ether catalysed reaction of cyclohepta-1,3-diene with p-benzoquinone gave good yields of the Diels-Alder adduct which was converted into hydroxyketone (3).Experiments with cyclohexanol and admantan-2-ol established characteristic 13C n.m.r. chemical shifts associated with deprotonation of alcohols by dimsyl sodium in dimethyl sulphoxide.Solutions of the sodium salts of (1)-(3) were prepared and dynamic 13C n.m.r. spectroscopy gave barriers for their degenerate rearrangement of >21.7 (100 deg C), 19.0 (100 deg C), and 17.3 (72 deg C) kcal mol-1, respectively.The relationship between variation of barrier and molecular geometry is discussed with the aid of empirical force field calculations.
Synthesis of 4,4′-spirobi[pentacyclo[5.4.0.02,6.03,10.05,9]undecane]
Shi, Yijun,Jiang, Jingyang,Wang, Jianzhi,Wang, Yanhua
, p. 6704 - 6706 (2015)
4,4′-Spirobi[pentacyclo[5.4.0.02,6.03,10.05,9]undecane] (10) is first successfully prepared by a nine step synthetic scheme starting from the key intermediate (cyclopentadiene derivate, 2). This synthetic scheme avoids using the hardly obtainable spiro[4.4]nonatetraene (18) as the starting material. In the structure of 10, two polycyclic cages share one spiro-carbon so that it has high density (1.2663 g/cm3) and high volumetric heat of combustion (53.353 MJ/L).
A convenient road to 1-chloropentacycloundecanes - A joint experimental and computational investigation
Sharapa, Dmitry I.,Gayday, Alexander V.,Mitlenko, Alena G.,Levandovskiy, Igor A.,Shubina, Tatyana E.
, p. 2554 - 2561 (2011)
An efficient synthetic strategy to obtain 1-chloro-Cs- trishomocubane and 1-chloro-D3-trishomocubane is described. 1-Chloro-Cs-trishomocubane is synthesized by a regioselective Diels-Alder reaction, and B3PW91/6-31G(d,p) calculations offer a plausible explanation of the reaction mechanism. Surprisingly, 1-chloro-C s-trishomocubane does not undergo an acid-catalyzed rearrangement to form 1-chloro-D3-trishomocubane and was obtained by chlorosulfation of Cookson's diketone. A possible mechanism of the reaction involving the formation of Cs- and D3-trishomocubane nonclassical cations was proposed on the basis of a mechanistic [B3PW91/6-31G(d,p) and MP2/cc-pVDZ] study. An efficient method to prepare 1-substituted pentacycloundecanes is described. Simple modification of the starting material for the Diels-Alder reaction gives 1-Cs-trishomocubane derivatives readily. Chlorosulfation of Cookson's diketone in four steps gives 1-chloro-D3-trishomocubane in good yields. The proposed mechanism of the reactions is explained by DFT and MP2 calculations. Copyright
Design, synthesis and evaluation of pentacycloundecane and hexacycloundecane propargylamine derivatives as multifunctional neuroprotective agents
Zindo, Frank T.,Malan, Sarel F.,Omoruyi, Sylvester I.,Enogieru, Adaze B.,Ekpo, Okobi E.,Joubert, Jacques
, p. 83 - 94 (2018/12/04)
The multifactorial pathophysiology of neurodegenerative disorders remains one of the main challenges in the design of a single molecule that may ultimately prevent the progression of these disorders in affected patients. In this article, we report on twelve novel polycyclic amine cage derivatives, synthesized with or without a propargylamine function, designed to possess inherent multifunctional neuroprotective activity. The MTT cytotoxicity assay results showed the SH-SY5Y human neuroblastoma cells to be viable with the twelve compounds, particularly at concentrations less than 10 μM. The compounds also showed significant neuroprotective activity, ranging from 31% to 61% at 1 μM, when assayed on SH-SY5Y human neuroblastoma cells in which neurodegeneration was induced by MPP+. Calcium regulation assays conducted on the same cell line showed the compounds to be significant VGCC blockers with activity ranging from 26.6% to 51.3% at 10 μM; as well as significant NMDAr antagonists with compound 5 showing the best activity of 88.3% at 10 μM. When assayed on human MAO isoenzymes, most of the compounds showed significant inhibitory activity, with compound 5 showing the best activity (MAO-B: IC50 = 1.70 μM). Generally, the compounds were about 3–52 times more selective to the MAO-B isoenzyme than the MAO-A isoenzyme. Based on the time-dependency studies conducted, the compounds can be defined as reversible MAO inhibitors. Several structure activity relationships were derived from the various assays conducted, and the compounds’ possible putative binding modes within the MAO-B enzyme cavity were assessed in silico.
A Small-Footprint, High-Capacity Flow Reactor for UV Photochemical Synthesis on the Kilogram Scale
Elliott, Luke D.,Berry, Malcolm,Harji, Bashir,Klauber, David,Leonard, John,Booker-Milburn, Kevin I.
supporting information, p. 1806 - 1811 (2016/10/31)
The development of a highly compact and powerful reactor for synthetic organic photochemistry is described enabling a 10-fold reduction in reaction times, with up to 30% more power efficiency than previous fluorinated ethylene propylene tube reactors. Two
