19234-05-0

Upstream product

• 90-46-0 9-hydroxyxanthene 
• 100-66-3 methoxybenzene 
• 19434-34-5 2-(phenoxy)benzaldehyde 
• 92-83-1 xanthene 
• 944668-33-1 C₂₀H₁₈O₃ 
• 123-11-5 4-methoxy-benzaldehyde 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 64-18-6 formic acid 
• 94465-25-5 9-(4-methoxyphenyl)-9H-xanthen-9-ol 
• 77-78-1 dimethyl sulfate 
• 90-47-1 xanth-9-one 
• 112305-00-7 9-(p-Methoxyphenyl)-xanthyl 
• 19355-10-3 1-benzyl-4-methyl-1,4-dihydronicotinamide 
• 952-92-1 1-Benzyl-1,4-dihydronicotinamide 

Downstream Products

• 94929-75-6 C₂₀H₁₅O₂^(1-) 
• 112305-00-7 9-(p-Methoxyphenyl)-xanthyl 
• 103019-26-7 bis-[9-(4-methoxy-phenyl)-xanthen-9-yl]-peroxide 

Relevant academic research and scientific papers

Intrazeolite photochemistry. 12. Ship-in-a-bottle synthesis and control of the photophysical properties of 9-(4-methoxyphenyl)xanthenium ion imprisoned into large-pore zeolites

The 9-(4-methoxyphenyl)xanthylium ion (AnX+), a bulky cation that according to molecular modeling simulations cannot enter through the 7.4 A pore opening of tridirectional large-pore zeolites Y and β, has been prepared by ship-in-a-bottle synthesis within the supercages of these two zeolites. The synthetic procedure involves two steps: (i) generation of xanthylium cation (X+) adsorbed within the zeolite by treatment of xanthydrol onto the H+ form of these solids; (ii) electrophilic attack of the cation to anisole within the framework of the zeolite. Carrying out the same procedure using toluene or benzene or using an alternative process involving the reaction of xanthone with anisole, led to the corresponding 9-arylxanthylium ions together with some unidentified adventitious material. Textural and acidic properties of these composites were tested using α-methylstyrene dimerization and were found to be very similar to the original HY or Hβ zeolites, thus indicating an internal location for AnX+. Entrapment within the zeolite framework restricts AnX+ conformational mobility, thwarting the deactivation pathway occurring in solution. This has allowed for the first time characterization of its triplet excited state as a long-lived transient species (tens of microseconds), as well as the observation of room-temperature fluorescence in the nanosecond range.

Substituent Effects on Temperature Dependence of Kinetic Isotope Effects in Hydride-Transfer Reactions of NADH/NAD+Analogues in Solution: Reaction Center Rigidity Is the Key

Substituent effects on the temperature dependence of primary kinetic isotope effects, characterized by ΔEa = EaD - EaH, for two series of the title reactions in acetonitrile were studied. The change from ΔEa ≈ 0 for a highly rigid system to ΔEa > 0 for systems with reduced rigidities was observed. The rigidities were controlled by the electronic and steric effects. This work replicates the observations in enzymes and opens a new research direction that studies structure-ΔEa relationship.

Graphene-Oxide-Catalyzed Direct CH?CH-Type Cross-Coupling: The Intrinsic Catalytic Activities of Zigzag Edges

The development of graphene oxide (GO)-based materials for C?C cross-coupling represents a significant advance in carbocatalysis. Although GO has been used widely in various catalytic reactions, the scope of reactions reported is quite narrow, and the relationships between the type of functional groups present and the specific activity of the GO are not well understood. Herein, we explore CH?CH-type cross-coupling of xanthenes with arenes using GO as real carbocatalysts, and not as stoichiometric reactants. Mechanistic studies involving molecular analogues, as well as trapped intermediates, were carried out to probe the active sites, which were traced to quinone-type functionalities as well as the zigzag edges in GO materials. GO-catalyzed cross-dehydrogenative coupling is operationally simple, shows reusability over multiple cycles, can be conducted in air, and exhibits good functional group tolerance.

Palladium-copper catalyzed C(sp3)-C(sp2) bond C-H activation cross-coupling reaction: Selective arylation to synthesize 9-aryl-9: H -xanthene and 9,9-diaryl-xanthene derivatives

A novel cooperatively catalyzed C(sp3)-C(sp2) bond C-H activation cross-coupling reaction has been developed. A series of 9-aryl-9H-xanthenes and 9,9-diaryl-xanthenes were selectively synthesized in moderate to good yields by control

Unusual Reaction Constant for Hydride Transfer from a Carbanion to 9-Arylxanthyliums

The reaction constant (ρ) from the kinetics for hydride transfer from a carbanion (XH-) to 9-arylxanthylium ions (9-GPhXn+) in CH3CN was unusually negative. Thermodynamic analysis indicated that ρ for the simple hydride tr

Structurally diverse α-substituted benzopyran synthesis through a practical metal-free C(sp3)-H functionalization

A trityl ion-mediated practical C-H functionalization of a variety of benzopyrans with a wide range of nucleophiles (organoboranes and C-H molecules) at ambient temperature has been disclosed. The metal-free reaction has an excellent functional group tole

A classical but new kinetic equation for hydride transfer reactions

A classical but new kinetic equation to estimate activation energies of various hydride transfer reactions was developed according to transition state theory using the Morse-type free energy curves of hydride donors to release a hydride anion and hydride acceptors to capture a hydride anion and by which the activation energies of 187 typical hydride self-exchange reactions and more than thirty thousand hydride cross transfer reactions in acetonitrile were safely estimated in this work. Since the development of the kinetic equation is only on the basis of the related chemical bond changes of the hydride transfer reactants, the kinetic equation should be also suitable for proton transfer reactions, hydrogen atom transfer reactions and all the other chemical reactions involved with breaking and formation of chemical bonds. One of the most important contributions of this work is to have achieved the perfect unity of the kinetic equation and thermodynamic equation for hydride transfer reactions. The Royal Society of Chemistry.

Sulfonic acid-catalyzed autoxidative carbon-carbon coupling reaction under elevated partial pressure of oxygen

An aerobic organocatalytic oxidative C-C bond formation reaction of benzylic C-H bonds with various C-nucleophiles is described. The coupling reaction proceeds by simply stirring the substrates under elevated partial pressure of oxygen in the presence of a sulfonic acid catalyst at room temperature. Elevation of the pressure enables the reaction of a broad scope of nucleophile substrates otherwise showing poor reactivity at ambient pressure. The benzylic C-H bonds of xanthene, acridanes, isochromane and related heterocycles could be functionalized with nucleophiles including ketones, 1,3-dicarbonyl compounds and aldehydes. Electron-rich arenes could be utilized as nucleophiles at elevated temperatures. The reactions are believed to proceed via autoxidation of the benzylic C-H bonds to the hydroperoxides and subsequent nucleophilic substitution catalyzed by sulfonic acids. Copyright

What are the differences between ascorbic acid and NADH as hydride and electron sources in vivo on thermodynamics, kinetics, and mechanism?

Ascorbic acid (AscH2) and dihydronicotinamide adenine dinucleotide (NADH) are two very important natural redox cofactors, which can be used as hydride, electron, and hydrogen atom sources to take part in many important bioreduction processes in vivo. The differences of the two natural reducing agents as hydride, hydrogen atom, and electron donors in thermodynamics, kinetics, and mechanisms were examined by using 5,6-isopropylidene ascorbate (iAscH-) and β-d-glucopyranosyl-1, 4-dihydronicotinamide acetate (GluNAH) as their models, respectively. The results show that the hydride-donating ability of iAscH- is smaller than that of GluNAH by 6.0 kcal/mol, but the electron-donating ability and hydrogen-donating ability of iAscH- are larger than those of GluNAH by 20.8 and 8.4 kcal/mol, respectively, which indicates that iAscH- is a good electron donor and a good hydrogen atom donor, but GluNAH is a good hydride donor. The kinetic intrinsic barrier energy of iAscH- to release hydride anion in acetonitrile is larger than that of GluNAH to release hydride anion in acetonitrile by 6.9 kcal/mol. The mechanisms of hydride transfer from iAscH- and GluNAH to phenylxanthium perchlorate (PhXn+), a well-known hydride acceptor, were examined, and the results show that hydride transfer from GluNAH adopted a one-step mechanism, but the hydride transfer from iAscH- adopted a two-step mechanism (e-H?). The thermodynamic relation charts (TRC) of the iAscH- family (including iAscH-, iAscH?, iAsc?-, and iAsc) and of the GluNAH family (including GluNAH, GluNAH?+, GluNA?, and GluNA+) in acetonitrile were constructed as Molecule ID Cards of iAscH- and of GluNAH in acetonitrile. By using the Molecule ID Cards of iAscH- and GluNAH, the character chemical properties not only of iAscH- and GluNAH but also of the various reaction intermediates of iAscH- and GluNAH all have been quantitatively diagnosed and compared. It is clear that these comparisons of the thermodynamics, kinetics, and mechanisms between iAscH- and GluNAH as hydride and electron donors in acetonitrile should be quite important and valuable to diagnose and understand the different roles and functions of ascorbic acid and NADH as hydride, hydrogen atom, and electron sources in vivo.

Scandium triflate-catalyzed one-pot domino approach towards general and efficient syntheses of unsymmetrical 9-substituted xanthene derivatives

A general and efficient one-pot cascade/tandem approach to synthesize unsymmetrical 9-aryl/heteroaryl xanthenes has been developed under extremely mild reaction conditions using 10 mol% Sc(OTf)3 as a catalyst. This strategy has been further extended to synthesize 9-(thioaryl) xanthenes through tandem carbon-sulfur (C-S) and carbon-carbon (C-C) bond formation. Novel C-C and C-S bond cleavage promoted by Sc(OTf)3 is also discussed during mechanistic investigation. The Royal Society of Chemistry.