942-57-4Relevant academic research and scientific papers
Birch Reductive Alkylation of Methyl m-(Hydroxymethyl)benzoate Derivatives and the Behavior of o- and p-(Hydroxymethyl)benzoates under Reductive Alkylation Conditions
Fretz, Samuel J.,Hadad, Christopher M.,Hart, David J.,Vyas, Shubham,Yang, Dexi
supporting information, p. 83 - 92 (2013/03/29)
Birch reductive alkylation of methyl m-(hydroxymethyl)benzoate derivatives, using lithium in ammonia-tetrahydrofuran in the presence of tertbutyl alcohol, can be achieved without significant loss of benzylic oxygen substituents. Similar treatment of o- and p-(hydroxymethyl)benzoate derivatives results largely in loss of benzylic oxygen substituents. The results are rationalized by computations describing electron density patterns in the putative radical anion intermediate involved in these reactions.
Benzohydroxamic acids as potent and selective anti-HCV agents
Kozlov, Maxim V.,Kleymenova, Alla A.,Romanova, Lyudmila I.,Konduktorov, Konstantin A.,Smirnova, Olga A.,Prasolov, Vladimir S.,Kochetkov, Sergey N.
, p. 5936 - 5940 (2013/10/22)
A diverse collection of 40 derivatives of benzohydroxamic acid (BHAs) of various structural groups were synthesized and tested against hepatitis C virus (HCV) in full-genome replicon assay. Some of these compounds demonstrated an exceptional activity, suppressing viral replication at sub-micromolar concentrations. The compounds were inactive against key viral enzymes NS3, and NS5B in vitro assays, suggesting host cell inhibition target(s). The testing results were consistent with metal coordination by the BHAs hydroxamic group in complex with a target(s). Remarkably, this class of compounds did not suppress poliomyelitis virus (PV) propagation in RD cells indicating a specific antiviral activity of BHAs against HCV.
Electrochemical reduction of methyl 2-bromomethylbenzoate at carbon cathodes in dimethylformamide containingwater
Allen, Caroline R.,Brown, Drew K.,Potts, Jessica L.,Ji, Chang
, p. G3069-G3072 (2013/07/05)
Cyclic voltammetry and controlled-potential electrolysis have been employed to examine the electrochemical reduction of methyl 2-bromomethylbenzoate at carbon cathodes in dimethylformamide (DMF) containing tetramethylammonium tetrafluoroborate (TMABF4). A cyclic voltammogram for the reduction of the substrate exhibits one irreversible cathodic wave with a peak potential of -1.45 V vs. SCE, which is due to the two-electron cleavage of the benzylic carbon-bromine bond. The corresponding reductive peak current also increases incrementally with the amount of water in DMF. Bulk electrolyses of methyl 2-bromomethylbenzoate have been carried out at -1.85 V vs. SCE with different concentrations of water in the solvent. The reduction process involves carbanion intermediates to afford various products including phthalide, which is generated via intramolecular cyclization that is affected by the presence of water. Detailed mechanism for the electrochemical reaction is proposed and further studied by isotope incorporation experiment.
Oxidation of Aromatic Compounds. II. Oxidation of Methyl Derivatives of Benzoic Acid and Acetophenone in the System HSO3F-PbO2
Rudenko, A. P.,Korovina, N. S.
, p. 1084 - 1088 (2007/10/03)
Low-temperature oxidation of methyl derivatives of benzoic acid and acetophenone in the system HSO3F-PbO2 proceeds with intermediate formation of radical cations and results in replacement of hydrogen atom in methyl group or benzene ring.The reaction allows preparation of various substituted derivatives of benzyl alcohols and alkylated phthalides.
THE ESR SPECTRA, STRUCTURE, AND REACTIVITY OF AROMATIC RADICAL-CATIONS IN SUPERACIDS
Rudenko, A. P.
, p. 1946 - 1980 (2007/10/03)
The oxidation of aromatic compounds by lead dioxide in superacids based on fluorosulfonic acid at -75 deg C takes place by a one-electron mechanism and leads in many cases to relatively stable radical-cations.The ESR spectra, the isotropic hyperfine coupling constants, data on the reactivity of the radical-cations, and the structures of the final products from their transformations under "long-life" conditions are presented.
Generation and Thermal Reactions of 2-Methyl-4-oxo-2-selenoniochroman-3-ide
Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Tsutsumi, Kazuhiro
, p. 1397 - 1400 (2007/10/02)
The thermal reaction of 2-methyl-4-oxo-2-selenoniochroman-3-ide (4) in aprotic solvents afforded (E)-bisbenzoyl>ethylene (5) and trans-1,2,3-trisbenzoyl>cyclopropane (6) via a carbene intermediate.Ethanol reacted thermally with 4 to open the chroman ring, giving ethyl 2-benzoate (9a) and ethyl 2-(ethoxymethyl)benzoate (10a), whereas reaction with methanol yielded only methyl 2-benzoate (9b).Hydrolysis of ylide 4 eliminated dimethyl selenide, giving phthalide and 2-(hydroxymethyl)benzoic acid.
