Refernces
10.1016/j.tet.2009.07.021
The study presents the synthesis and characterization of a new class of fluorescent nucleosides with 2-aryl-3-hydroxychromone (3-HC) as base analogues. These nucleosides, specifically 1a and 1b, were designed to incorporate into DNA oligonucleotides for sensitive fluorescence-based detection and imaging. The synthesis involved key steps like aryl-aldol condensation, cycloetherification, Friedel-Crafts glycosylation, and 1,3-dipolar cycloaddition. The resulting nucleosides exhibited dual emission sensitivity to polarity changes, with 1a showing high sensitivity, making it promising for nucleic acid labeling and tracking environmental changes within DNA structures. The study provides a foundation for developing more advanced fluorescent probes for biological applications.
10.1021/jo502623g
The study presents a novel and efficient method for the reduction of tertiary hydroxyalkylphosphine oxides to the corresponding tertiary hydroxyalkylphosphine-boranes using borane (BH3) as a mild reducing agent. This direct and stereoselective conversion is facilitated by the presence of an α- or β-hydroxy group in the phosphine oxide structure, which enables an intramolecular P≡O···B complexation. The study demonstrates that the reduction of the P≡O bond occurs with complete inversion of configuration at the phosphorus center. The method's mild conditions and high yields make it a valuable approach for the synthesis of organophosphorus compounds, particularly those that are functionalized and/or nonracemic. The research also includes the exploration of the stereochemical course of the reduction and the role of the hydroxyl group in the reduction process, providing insights into the mechanism and potential applications in organic chemistry.
10.1016/j.tetlet.2014.01.056
The research presents a study on a selective fluorescence turn-on detection method for hydrogen peroxide (H2O2) and D-glucose, utilizing a tetraphenylethylene (TPE)-based molecule, compound 1. The detection mechanism relies on the aggregation-induced emission (AIE) behavior of the TPE unit and the reaction of H2O2 with the arylboronic ester group in compound 1. Upon reaction with H2O2, compound 1 transforms into compound 2, which is less soluble in water, leading to aggregation and a consequent fluorescence turn-on due to AIE properties. The study also demonstrates the application of compound 1 for the selective detection of D-glucose in aqueous solutions, leveraging the enzymatic oxidation of D-glucose by glucose oxidase (GOx) to produce H2O2, which then reacts with compound 1. The experiments involved the synthesis of compound 1, its characterization using 1H NMR, 13C NMR, and mass spectra, and fluorescence spectroscopy to monitor the reaction with H2O2 and the detection of D-glucose. The results showed high selectivity and sensitivity for H2O2 detection, with a low detection limit of 180 nM, and successful D-glucose detection down to a concentration of 3.0 μM. The selectivity was confirmed by testing the fluorescence response of compound 1 to other reactive oxygen species and sugars, with significant enhancement observed only in the presence of H2O2 and D-glucose.
10.1246/cl.1994.1307
The research investigates the ring hydroxylation of aromatic amino acid derivatives and toluene catalyzed by manganese halogenated porphyrins in CHCl3/H2O and lipid bilayers. The study finds that manganese fluorinated porphyrins can catalyze the ring hydroxylation of phenylalanine derivatives and toluene with hydrogen peroxide, and the hydroxylation is enhanced in phospholipid bilayers when imidazole is present. The hydroxylation depends on the structures of the porphyrins and substrates. The results suggest that the hydrophobic moiety of the substrate plays an important role in the ring hydroxylation in lipid bilayers, and the concentration of imidazole is crucial for the hydroxylation.
10.1016/j.tet.2007.02.082
The study focuses on the synthesis, stereochemical analysis, and functional transformations of 2-phenylselanyl-1,3-dienes. The researchers prepared these dienes using Wittig or Wittig-Horner-Emmons reactions, starting from α-phenylselanyl α,β-unsaturated aldehydes. They determined the ratio and configuration of the diene isomers using 77Se and 1H NMR spectroscopy. The dienes were then oxidized to selenoxides, which underwent [2,3]-sigmatropic rearrangements in THF, leading to the formation of allenyl alcohols, allenyl carbamates, and 1-haloalkyl allenes. This work explores the potential of selenoxides, selenimides, and dihalo-selenuranes in organic synthesis, providing a mild and selective method for preparing various functionalized allenes. The study also discusses the implications of these findings in the context of organic synthesis, including the potential use of these compounds in Diels-Alder cycloaddition reactions and as precursors for other synthetic transformations.
10.1002/hc.1044
The research centers on the synthesis and assessment of metal-ion transport capabilities of newly crafted thiamacrocycles, which incorporate thiol and disulfide groups within their structure. These compounds were designed to selectively transport heavy metal ions, with a particular focus on silver ions (Ag?). The synthesis involved multiple steps, beginning with the preparation of diol and ditosylate intermediates, which then reacted under high dilution conditions to form cyclic dibromides. These were further transformed into dithiol hosts through lithiation and reaction with elemental sulfur, followed by oxidation to disulfide hosts using hydrogen peroxide and potassium carbonate. The synthesized thiamacrocycles were then tested for their metal-transport ability using a dual cylindrical apparatus, where the hosts were dissolved in a liquid membrane, and metal nitrate solutions were used as the source. After 24 hours, the transport of metal ions into the receiving phase was quantified by atomic absorption spectroscopy, revealing high selectivity for Ag?. The study utilized various reactants and analytical techniques, such as NMR, IR spectroscopy, and mass spectrometry, to characterize the synthesized compounds and understand the factors influencing their metal-binding preferences.
10.1080/14786419.2015.1075525
The research focuses on the utilization of hydrotalcite catalysis for the synthesis of novel chiral building blocks, specifically lactones 7 and 8, derived from carvone. The methodology involves a regioselective Baeyer–Villiger reaction using hydrogen peroxide as the oxidant and hydrotalcites as catalysts, which is considered green due to the lack of by-products other than water. The study compares different reaction conditions, including the use of AlCl3 and meta-chloroperbenzoic acid (m-CPBA) as oxidants, and evaluates the efficiency of the catalysts in terms of yield and selectivity. Reactants such as carvone, benzonitrile, and various catalysts were used, and the progress of reactions was monitored by thin-layer chromatography (TLC). Analyses of the synthesized compounds were conducted using techniques like infrared spectroscopy (IR), nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS) to determine their structures and confirm their formation.
10.1021/jo00308a030
The study focuses on the synthesis of 1,4-dinitroanthracene-9,10-dione (2) and its subsequent transformations using various diamines. The researchers explored two methods for synthesizing 2, one involving trifluoroacetic anhydride and hydrogen peroxide, and the other using trifluoroacetic acid and hydrogen peroxide. They then investigated the displacement of the nitro groups in 2 by different diamines, such as N,N-dimethylethylenediamine, 2-[(2-aminoethyl)amino]ethanol, and ethylenediamine, to produce monosubstituted and bis-substituted anthracene-9,10-dione derivatives. The study also examined the sequential displacements of the nitro substituents by diamines to prepare unsymmetrically substituted 1,4-bis[(aminoalkyl)amino]anthracene-9,10-diones. The products were characterized using various analytical techniques, including melting point determination, proton NMR, and mass spectrometry.
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