Category: 596-38-3

Llama, Emilio F. published the artcileSynthesis and antinociceptive activity of 9-phenyl-9-alkoxy or 9-acyloxy derivatives of xanthene, thioxanthene and acridine, Category: alcohols-buliding-blocks, the publication is European Journal of Medicinal Chemistry (1989), 24(4), 391-6, database is CAplus.

9-Phenyl-9-(alkoxy or acyloxy) derivatives of xanthene, thioxanthene, and acridine I (X = O, S, NH, NMe; R = Me, Et, Ac, COEt) are prepared by PhLi or PhMgBr addition to xanthone, thioxanthone or acridone followed by derivatization of the resultant hydroxy group. I (X = O, S; R = COEt) demonstrated potent antinociceptive activity.

European Journal of Medicinal Chemistry published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Barton, Benita published the artcileAn investigation of the complexation of host N,N’-bis(9-phenyl-9-thioxanthenyl)ethylenediamine with dihaloalkane guests, Related Products of alcohols-buliding-blocks, the publication is Journal of Inclusion Phenomena and Macrocyclic Chemistry (2017), 89(1-2), 105-116, database is CAplus.

Two wheel-and-axle host compounds were synthesized and assessed for their host ability. After growing crystals of N,N’-bis(9-phenyl-9-thioxanthenyl)ethylenediamine from various alkyl halide solvents, we discovered that this host is highly proficient for the enclathration of these guest types. However, the novel compound N,N’-bis(9-phenyl-9-xanthenyl)-1,6-hexamethylenediamine, bearing the more flexible axle, showed no inclusion ability whatsoever. Competition experiments where the title host compound was recrystallized from equimolar binary and ternary mixtures of CH₂Cl₂, CH₂Br₂ and CH₂I₂ showed this host to have a selectivity in the order CH₂Br₂ > CH₂I₂ > CH₂Cl₂ for these guests. Varying the molar ratios of guests in these mixtures beyond equimolar revealed that the host remained selective for the bromine derivative whenever it was present, even at low dibromomethane concentrations Single crystal X-ray diffraction data and, more specifically, host-guest interactions in the crystal, were used to explain the selectivity order; lattice energies were also considered in this context. The relative thermal stabilities of the three complexes, obtained from thermal experiments, showed that the selectivity order and these thermal stabilities are unrelated.

Journal of Inclusion Phenomena and Macrocyclic Chemistry published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Minto, Robert E. published the artcileLaser flash photolysis study of photodehydroxylation phenomena of 9-phenylxanthen-9-ol and photobehavior of related intermediates. Enhanced electrophilicity of 9-phenylxanthenium cation singlet, Recommanded Product: 9-Phenyl-9H-xanthen-9-ol, the publication is Journal of the American Chemical Society (1989), 111(24), 8858-66, database is CAplus.

In the course of 248-nm laser flash photolysis, solutions of 9-phenylxanthen-9-ol (I) undergo homolytic and heterolytic photodehydroxylation, the relative efficiency of which depends strongly on the solvent nature. Polar/hydroxylic solvents, especially aqueous mixtures, cause copious formation of 9-phenylxanthenium cation (II), the ground- and excited-state properties of which are conveniently studied by single- and double-laser flash photolysis. In 1:1 H₂O/MeCN, the quantum yield of carbenium ion generation is 0.4 ± 0.1, only 2% of which evolves through an adiabatic route. In polar but nonhydroxylic solvents (e.g., MeCN and CH₂ClCH₂Cl) also, the cation is photogenerated in small yields sufficient for time-resolved spectroscopic detection and study in these relatively neutral and inert media. In relatively nonpolar solvents, e.g., n-heptane and C₆H₆, photolysis of I is dominated by homolytic cleavage to 9-phenylxanthenyl radical III. The short-lived triplets of I (τ_T ≤ 0.3 μs) are also observed in nonaqueous solvents (ϕ_T = 0.05 in MeCN). In comparison to the weak, fast-decaying, double-doublet fluorescence of III (λ_max^F = 590 nm, τ_F ≤ 5 ns), the singlet-singlet fluorescence from II is intense and long-lived (λ_max^F = 550 nm, τ_F = 25 ns in MeCN in the absence of nucleophilic quenchers) and is almost nonquenchable by oxygen (k_q ≤ 5 × 10⁸M^-1 s^-1). The electrophilicity of the lowest excited singlet state of II, measured in terms of rate constants (k_q) of bimol. quenching by anions and lone-pair containing mols., is considerably more pronounced than that of the ground state (i.e., k_q‘s are higher for the excited state by several orders of magnitude).

Journal of the American Chemical Society published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Recommanded Product: 9-Phenyl-9H-xanthen-9-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Arnett, Edward M. published the artcileMaster equations for calculating heterolysis energies in solution, Recommanded Product: 9-Phenyl-9H-xanthen-9-ol, the publication is Energy & Fuels (1987), 1(1), 17-23, database is CAplus.

The title LFER, in which carbocation stability is represented by the π-delocalization energy instead of k_R⁺, correlates. The reactions of six carbocations with twenty-one carbanions and five phenoxides with excellent statistical accuracy and self-consisting. This equation can be used to predict the bond heterolysise enthalpies when resonance stabilized ions are formed.

Energy & Fuels published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Recommanded Product: 9-Phenyl-9H-xanthen-9-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Barton, Benita published the artcileSynthesis of N,N’-bis(9-phenylxanthen-9-yl)ethylenediamine and an investigation of its host-guest inclusion potential, SDS of cas: 596-38-3, the publication is Perkin 2 (2000), 865-869, database is CAplus.

The novel amine, N,N’-bis(9-phenylxanthen-9-yl)ethylenediamine (I), was synthesized by treating 9-phenylxanthen-9-ylium perchlorate with ethylenediamine. Its host potential was assessed by allowing it to crystallize from a range of organic solvents (single and binary mixtures), of which several were found to be included. The stoichiometries of these host-guest complexes were determined through ¹H-NMR anal. and their stabilities assessed through thermal anal. Single crystal x-ray crystallog. was used to elucidate the crystal structure of the 1:1 I·THF inclusion complex. It was found that only one of the two amine moieties of the host functions as a donor, forming a nearly linear hydrogen bond to the oxygen atom of the guest mol. Each THF mol. is effectively surrounded by host mols. so that the THF mols. are found to occupy discrete “cavities” within the host lattice. The activation energy associated with desolvation of the I·THF complex was determined through thermal anal. and was found to decrease as desolvation progressed.

Perkin 2 published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, SDS of cas: 596-38-3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Valentino, Maria R. published the artcileQuenching behavior of singlet excited 9-arylxanthylium cations, Computed Properties of 596-38-3, the publication is Journal of Organic Chemistry (1993), 58(21), 5826-31, database is CAplus.

Several 9-arylxanthylium tetrafluoroborate salts (Ar = H, p, m-F, p, m-Me, m-OMe) were synthesized by reaction of the corresponding 9-arylxanthen-9-ol with fluoroboric acid. Spectral characteristics of the xanthyl cations were identical to those previously reported for the cations generated by alternate methods. The 9-arylxanthyl cation fluorescence was quenched by the addition of H₂O, MeOH, i-PrOH, and t-BuOH. Stern-Volmer anal. of the fluorescence quenching gave bimol. excited-state rate constants ranging from 10⁶ to 10¹⁰ M^-1 s^-1, with the larger rate constants associated with electron-donating substituents. Hammett plots of log[k_q(X)/k_q(H)] vs. σ^hv gave neg. ρ values for each quencher, opposite to the substituent dependence observed for ground-state cations reacting with nucleophiles. The relative quenching order also differs from the order observed for ground-state cation reactions. The mechanism for quenching of the singlet excited 9-arylxanthylium cations is evaluated in terms of nucleophilic attack. The possibility of an electron-transfer mechanism is considered and eliminated.

Journal of Organic Chemistry published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C6H8BNO3, Computed Properties of 596-38-3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Misetic, Ana published the artcileThe pixyl (Px) group: a novel photocleavable protecting group for primary alcohols, Related Products of alcohols-buliding-blocks, the publication is Tetrahedron Letters (1998), 39(13), 1653-1656, database is CAplus.

The 9-phenylxanthyl (pixyl or Px) moiety has been investigated as a potential photocleavable protecting group for primary alcs. Alcs. were protected in good yield by treatment with 9-chloro-9-phenylxanthene in dry pyridine at room temperature Irradiation of the alc. derivatives in neutral aqueous acetonitrile regenerates the alcs. and the 9-phenylxanthyl alc.

Tetrahedron Letters published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Azarani, A. published the artcileElectron transfer reactions between excited diarylmethyl and triarylmethyl carbocations and aromatic donors, Computed Properties of 596-38-3, the publication is Journal of Photochemistry and Photobiology, A: Chemistry (1991), 57(1-3), 175-89, database is CAplus.

The excited singlet states of diarylmethyl and triarylmethyl carbocations were characterized by fluorescence. The dibenzosuberenyl, xanthenyl, and 9-phenylxanthenyl cations are strongly fluorescent and have fluorescence lifetimes in the 30-40 ns range in 2,2,2-trifluoroethanol. The fluorescence of each of these cations is efficiently quenched by a variety of substituted aromatics (e.g., cumene, anisole, toluene) with rate constants in excess of 10⁹ M^-1 s^-1. There is a correlation between the observed rate constants and the oxidation potential of the aromatic quencher which suggests that an electron transfer process occurs to generate a radical/radical cation pair. This hypothesis is confirmed by irradiation of the dibenzosuberenyl cation in the presence of benzyltrimethylsilane. This reaction produces 5-benzyldibenzocycloheptene, which is formed by addition of the benzyl radical produced via cleavage of the silane radical cation to either the dibenzosuberenyl radical or cation. Quenching studies suggest that the efficiency of product formation is controlled by the competition between cage escape and back electron transfer for the initial geminate radical/radical ion pair.

Journal of Photochemistry and Photobiology, A: Chemistry published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Computed Properties of 596-38-3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

McClelland, Robert A. published the artcileElectrophilic reactions of xanthylium carbocations produced by flash photolysis of 9-xanthenols, Quality Control of 596-38-3, the publication is Journal of the American Chemical Society (1989), 111(8), 2929-35, database is CAplus.

The xanthylium ion and eight 9-aryl derivatives (p-MeO-, p-Me-, m-Me-, H-, p-F-, m-MeO-, p-Cl-, and p-CF₃C₆H₄) were produced in 1:4 acetonitrile/water by flash photolysis of the corresponding 9-xanthenols. The identifications of the transients as xanthylium cations were based upon their characteristic absorption spectra, as well as upon experiments with time-resolved conductivity detection. Rate constants for the reactions of these cations with solvent, with four anionic nucleophiles, and with four neutral nucleophiles (primary amines) were measured. The 9-arylxanthylium ions, which have solvent rate constants (k(solv)) at 25° ranging from 11 to 34 s^-1, follow the Ritchie equation, a plot of log k(nucleophile) vs. the nucleophile N₊ parameter being linear with a slope near unity. For the more reactive parent cation, which has k(solv) at 20° of 2.3 × 10⁴ s^-1, the rate constants k(nucleophile) are more poorly correlated with N₊ and the slope is less than unity. The failure to obey the Ritchie relationship is suggested to be associated with the rate constants becoming controlled by diffusion (azide ion) or desolvation (amines).

Journal of the American Chemical Society published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Quality Control of 596-38-3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Schonberg, Alexander published the artcileAction of Grignard reagents. II. Replacement of the oxygen atoms of ketones by two hydrocarbon radicals by the action of Grignard reagents, Recommanded Product: 9-Phenyl-9H-xanthen-9-ol, the publication is Journal of the Chemical Society (1946), 609-10, database is CAplus.

cf. C.A. 39, 65.1. PhMgBr (from 15 g. PhBr) and 5 g. xanthone in 40 cc. ether and 30 cc. C₆H₆, refluxed 5 hrs., allowed to stand overnight, and the residue extracted repeatedly with petr. ether, give, in addition to the main product [phenylxanthydrol (I)], 0.5 g. of 9,9-diphenylxanthene [Ullmann and Engi, Ber. 37, 2367(1904), reported only I]. Similarly, o-MeC₆H₄MgBr yields 9,9-di-o-tolylxanthene, m. 119°. 2,3,6,5-Dithianaphtheno-1,4-thiapyrone (II)(Part I) and PhCH₂MgCl in ether-C₆H₆, refluxed 5 hrs. and the product decomposed with dilute HCl, give 4,4-dibenzyl-2,3,6,5-dithianaphtheno-1,4-thiapyran (III), m. 176°; it does not react with Ac₂O; the concentrated H₂SO₄ solution is yellow. In another experiment the product was 4-hydroxy-4-benzyl-2,3,6,5-dithianaphtheno-1,4-thiapyran, light yellow, m. 220°; refluxed with Ac₂O for 3 hrs., it yields the 4-benzylidene derivative, light yellow, m. 244°. II and PhMgBr give the 4,4-diphenyl homolog of III, yellow, m. 235°, and m-MeC₆H₄MgBr yields the 4,4-ai-m-tolyl homolog, yellow, m. 219°. (p-MeC₆H₄)₂O (10 g.), 25 g. (COCl)₂, 10 g. AlCl₃ and 75 cc. CS₂ give 80% of 2,7-tlimethylxanthone.

Journal of the Chemical Society published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Recommanded Product: 9-Phenyl-9H-xanthen-9-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts