63007-45-4Relevant academic research and scientific papers
Direct Oxidation of Csp3?H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow
Lesieur, Mathieu,Battilocchio, Claudio,Labes, Ricardo,Jacq, Jér?me,Genicot, Christophe,Ley, Steven V.,Pasau, Patrick
supporting information, p. 1203 - 1207 (2019/01/04)
A fast, scalable, and safer Csp3?H oxidation of activated and un-activated aliphatic chains can be enabled by methyl(trifluoromethyl)dioxirane (TFDO). The continuous flow platform allows the in situ generation of TFDO gas and its rapid reactivity toward tertiary and benzylic Csp3?H bonds. The process exhibits a broad scope and good functional group compatibility (28 examples, 8–99 %). The scalability of this methodology is demonstrated on 2.5 g scale oxidation of adamantane.
Unprecedented stereochemical control in the intramolecular ene-reactions of δ,ε-unsaturated aldehydes using exceptionally bulky organoaluminum reagents: Elucidation of the transition state
Ooi,Maruoka,Yamamoto
, p. 6505 - 6522 (2007/10/02)
Unprecendented stereochemical control has been achieved in the type II intramolecular ene reactions of δ,ε-unsaturated aldehydes leading to trans-cyclohexanols with excellent selectivity under very mild conditions, using exceptionally bulky methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR). Success of the stereocontrolled cyclization can be ascribable to the ability of this modified organoaluminum reagents, MABR, to change the conformation of the transition state. Examining the ene reactions of substrates 7, 11, 14 with MABR, the stereochemical outcome of the present organoaluminum-promoted intramolecular ene reactions is further elucidated.
Oxidations of Alkylbenzenes with Dimethyldioxirane
Kuck, Dietmar,Schuster, Andreas
, p. 1223 - 1226 (2007/10/02)
Dioxiranes, Dimethyldioxirane, Alkylbenzenes, Oxidation The oxidation of various alkylbenzenes (1-17) with excess dimethyldioxirane (DMDO) in homogeneous acetone solutions has been studied.In general, the benzylic methylene and methine C-H bonds were oxidized to give the corresponding phenones and tertiary benzylic alcohols, respectively, in relatively low yields.Whereas a tert-butyl substituent at the reaction centre leads to very low conversion due to steric hindrance, the presence of additional phenyl groups appears to favour the oxidation in most,but not all cases.Di- and triphenylmethane (4 and 14) were found to be considerably less reactive than cis-decalin.By contrast, the intramolecular competetive oxidation of isobutylbenzene (19) and 1-methyl-4-phenylcyclohexanes (20) reveals that the benzylic C-H bonds are slightly more reactive than the tertiary ones at remote positions.
Synthesis and Anticonvulsant Activity of 1-Phenylcyclohexylamine Analogues
Thurkauf, Andrew,Costa, Brian de,Yamaguchi, Shun-ichi,Mattson, Mariena V.,Jacobson, Arthur E.,et al.
, p. 1452 - 1458 (2007/10/02)
Thirty-eight analogues of 1-phenylcyclohexylamine (PCA), a phencyclidine (PCP) derivative, were examined for their activities in the mouse maximal electroshock (MES) seizure test and in a motor-toxicity assay.In addition, we determined the binding affinities of the compounds for PCP acceptor sites in rat brain membranes labeled with -1-piperidine.Many of the analogues were protective against MES seizures (ED50s of 4-41 mg/kg, ip) and all of these compounds caused motor toxicity.The potencies in the motor toxicity and MES seizure tests showed a moderate correlation with the affinities for PCP sites.Several analogues exhibited a greater separation of potencies in the motor toxicity and MES seizure tests than did the parent compound PCA.These were obtained by (i) 3-methylation of the cyclohexyl ring trans to the phenyl ring, (ii) methoxylation at the ortho position on the phenyl ring, and (iii) contraction of the cyclohexane ring to form the corresponding cyclopentane.
