170798-94-4Relevant academic research and scientific papers
Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB)
Ramu, Ravirala,Chang, Chun-Wei,Chou, Ho-Husan,Wu, Li-Lan,Chiang, Chih-Hsiang,Yu, Steve S.-F.
supporting information; experimental part, p. 2950 - 2953 (2011/06/23)
gem-Difluoromethylene substituted molecules constitute a distinct class of fluorinated compounds. In this study, special chemistry has been developed for their preparation based on the highly selective terminal hydroxylation of these gem-difluorinated oct
Pentacoordinate organoaluminum chemistry: Catalytic efficiency of Me3Al in the epoxide cleavage with alkynyllithiums
Ooi,Kagoshima,Ichikawa,Maruoka
, p. 3328 - 3333 (2007/10/03)
A new and highly effective catalytic method for epoxide alkynylations has been developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me3Al via pentacoordinate organoaluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether, (1-benzyloxy)-3-butene oxide (1), in toluene with PhC?CLi under the influence of catalytic Me3Al (10 mol%) proceeded smoothly at 0 °C for 5 h to furnish the alkynylation product, 1-(benzyloxy)-6-phenylhex-5-yn-3-ol, in 76% yield [cf. 3% without Me3Al catalyst; 78% with stoichiometric Me3Al under similar conditions]. This represents the first catalytic procedure for the amphiphilic alkylation of epoxides. The participation of pentacoordinate Me3Al complexes of epoxy ethers of type 1 is emphasized by comparing the reactivity with the corresponding simple epoxide, 5-phenyl-1-pentene oxide, which was not susceptible to nucleophile attack of PhC?CLi with catalytic Me3Al under similar conditions. The pentacoordinate complex formation of Me3Al with epoxy ether 1 is characterized by low-temperature 13C and 27Al NMR spectroscopy. This approach is also applicable to the selective alkynylation of tosyl aziridines with adjacent ether functionality, which provides a promising method for amino alcohol synthesis.
18F-labeled octanoates as potential agents for cerebral fatty acid studies. The influence of 4-substitution and the fluorine position on biodistribution.
Nagatsugi,Inoue,Sasaki,Maeda
, p. 607 - 615 (2007/10/02)
In order to understand the structural features that might lead to an in vivo radiotracer for studying cerebral fatty acid metabolism, 8-[18F]fluorooctanoate derivatives with methyl or gem-dimethyl branching at the C4 position have been prepared. 3-[18F]Fluoro- and 4-[18F]fluorooctanoic acid have also been synthesized for studying the influence of the fluorine position on the in vivo behavior of 18F-labeled octanoic acid analogs. Radiochemical synthesis was achieved by the nucleophilic displacement of a tosylate or mesylate precursor with [18F]fluoride ion. Tissue distribution studies in rats showed low cerebral uptakes of these 18F-labeled fatty acid analogs with poor brain-to-blood ratios. 3-[18F]Fluorooctanoic acid showed considerable defluorination, evident as a high bone activity level. The initial uptake of activity in the brain after injection of ethyl 8-[18F]fluoro-4-methyloctanoate and 4-[18F]-fluorooctanoic acid remained virtually unchanged over an extended time period, similar to that previously observed for the unbranched analogs, ethyl 8-[18F]fluorooctanoate and its free acid. In contrast, the 4-gem-dimethyl branched analog was rapidly and preferentially taken up by the liver. It was shown in the metabolite analysis that labeled metabolites produced from 8-[18F]fluoro-4-methyloctanoic acid were found in blood, and that they could enter the brain to a significant degree. Thus, the present studies showed that radioactivity retention in the brain in the case of the 4-methyl branched analog was mainly attributable to its radioactive metabolites.
