106342-09-0

Upstream product

• 5026-62-0 sodium methylparaben 
• 3136-02-5 2-chlorotetrahydro-2H-pyran 
• 142-68-7 TETRAHYDROPYRANE 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 124361-07-5 2-<4-(tetrahydropyranyloxy)phenyl>-2-propanol 
• 1385024-05-4 [(η5-C5H5)Fe(η5-C5H4(p-C6H4-O-(tetrahydropyranyl)))] 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 1173046-26-8 3-oxo-3-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-propionitrile 
• 836608-61-8 4-(11-methacryloyloxyundecyloxycarbonyl)phenyl 7-[4-((S)-2-methylbutoxy)]-2-oxo-2H-1-benzopyran-3-carboxylate 
• 35486-97-6 4-(3,4,5,6-tetrahydropyran-2-yloxy)benzoic acid 

Relevant academic research and scientific papers

Thiosemicarbazone organocatalysis: Tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation

The first use of thiosemicarbazone-based organocatalysis was demonstrated on both tetrahydropyranylation and 2-deoxygalactosylation reactions. The organocatalysts were optimised using kinetics-based selection. The best catalyst outperformed previously reported thiourea catalysts for tetrahydropyranylation by 50-fold. Hammett investigations of both the organocatalyst and the substrate indicate an oxyanion hole-like reaction mechanism.

The construction of C(sp3)–O bond via copper porphyrin catalyzed cross-dehydrogenative coupling reaction: Substituent and electronic effect of the catalysts

The push-pull electronic and steric effect of copper porphyrin catalysts on the cross-dehydrogenative coupling (CDC) reaction between the hydroxyl group of phenol substrates and C(sp3)-H bond have been investigated. Results showed that copper porphyrin bearing electron-withdrawing, bulky steric hindrance or heteroatom of pyridyl groups could increase the catalytic activity in the reaction. 5,10,15,20-(tetrakis(4-pyridyl)porphyrin)copper (CuTPyP) was found the best among all tested catalysts. Phenol substrates bearing various functional groups afforded moderate to excellent yields (99%). Significantly, as compared to other tested copper porphyrins, CuTPyP not only exhibited remarkable higher activity but also could shorten the reaction time from 12 to 6 h.

Construction of C–O bond via cross-dehydrogenative coupling of sp [ 3] C–H bond with phenols catalyzed by copper porphyrin

Copper porphyrin-catalyzed construction of ether bond by cross-dehydrogenative coupling of sp [3] C–H bond with phenols bearing electron-withdrawing groups (EWG) was described for the first time. A broad range of substrates afforded different acetals in m

A BISPHENOL DERIVATIVE HAVING AN ESTER BOND

PROBLEM TO BE SOLVED: To provide a production intermediate useful for obtaining a compound having an ester bond, and a production method to obtain a compound having an ester bond, using the same, with convenience and high purity; specifically, to provide a bisphenol derivative having an ester bond, a method for producing the same, and a compound produced from the bisphenol derivative as an intermediate; and to further provide a polymer obtained by the polymerization of a polymerizable composition containing the compound produced from the bisphenol derivative as an intermediate, and an optical anisotropic body using the polymer. SOLUTION: A bisphenol derivative having an ester bond is represented by general formula (I-C), where at least one of A1 and A2 is substituted with one substituent L. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

Stepwise construction of a 4-hydroxyphenyl functionalized O,N,N-tridentate ferrocene-containing enaminone: Spectral, analytical and structural studies

Tetrahydropyranylation of methyl-4-hydroxybenzoate proceeds with formation of its corresponding THP aromatic ether THP-O-p-C6H 4CO2CH3 (1; THP = tetrahydropyranyl, C 5H9O). Reaction with in

COMPOUNDS USEFUL AS ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTOR AGONISTS

The present invention provides compounds and compositions, and methods of using them to modulate α7 nicotinic acetylcholine receptors and/or to treat any of a variety of disorders, diseases, and conditions. Provided compounds can affect, among other thing

Photosensitized tetrahydropyran transfer

(Chemical Equation Presented) THP ethers were formed cleanly during photolysis of 3,4-dihydro-2H-pyran, an alcohol, and catalytic 1,5-dichloro9,10-anthraquinone with use of visible light. The reaction could be conducted under ambient fluorescent lighting or with sunlight as well as in a Rayonet reactor. The scope and mechanism are discussed.

Synthesis and investigation of photophysical and photochemical properties of new side-group liquid crystalline polymers containing coumarin moieties

Four coumarin (2-oxo-2H-1-benzopyran) containing liquid crystalline polymethacrylates possessing the same monomer formula but different linkage directions and/or construction directions of their mesogens into the same main-chain were prepared and investigated. Each of the four polymers exhibits a smectic A liquid crystalline phase. The change of construction and/or linkage directions significantly affected their liquid crystalline properties. Especially, the change of the construction directions of the mesogens caused different photophysical and photochemical properties.

Intramolecular general-acid and electrostatic catalysis in acetal hydrolysis. Hydrolysis of 2-(substituted phenoxy)-6-carboxytetrahydropyrans and 2-alkoxy-6-carboxytetrahydropyrans

Rate constants have been determined for hydrolysis of a series of trans-2-(substituted phenoxy)-6-carboxytetrahydropyrans (e,a) in H2O and 50% dioxane-H2O. The second-order rate constant (k2) for the apparent hydronium ion catalyzed reaction of the anionic species of the p-nitro derivative in 50% dioxane-H2O (50 °C) is 620-fold larger than the second-order rate constant for hydrolysis of 2-(p-nitrophenoxy)tetrahydropyran. The slope (p) of the Hammett plot of log k2 vs σ is approximately 0, which supports a mechanism involving intramolecular general-acid catalysis by the un-ionized carboxyl group with proton transfer to the leaving group oxygen. Sizable catalytic effects can therefore be obtained in an intramolecular general-acid-catalyzed reaction when the leaving group is sufficiently good, even though the steric fit is poor and proton transfer may necessarily occur via an intervening water molecule. Intramolecular general-acid-catalyzed ring opening is not a favorable in the hydrolysis of tetrahydropyranyl acetals; such a mechanism does not occur in the hydrolysis of 2-alkoxy-6-carboxytetrahydropyrans. In the pH-independent decomposition of 2-(p-nitrophenoxy)-6-carboxytetrahydropyran at pH >6, the neighboring carboxylate anion participates electrostatically in 50% dioxane-H2O and gives a 10-fold rate enhancement. The plot of log kobed vs pH for hydrolysis of 2-(o-carboxyphenoxy)-6-carboxytetrahydropyran is bell shaped, which indicates that the monoanionic species is maximally reactive. The rate enhancement in that reaction in comparison with the hydrolysis of 2-(p-carboxyphenoxy)-6-carboxytetrahydropyran or 2-(p-carboxyphenoxy)tetrahydropyran is a factor of (2-4) × 103 in H2O but is 104-105 in 50% dioxane-H2O. The o-carboxyl group acts as an intramolecular general acid. However, bifunctional catalysis does not take place in this system. The lack of efficient electrostatic facilitation of these reactions by a neighboring carboxylate anion is most likely due to the energy expenditure for the 6-carboxylate group to approach the developing oxocarbonium ion closely. There is no chemical support for proposed mechanisms of lysozyme-catalyzed reactions that involve intracomplex general-acid-catalyzed opening of an unstrained hexose ring or large electrostatic stabilization effects by Asp-52.

The conformational behaviour of 2-aryloxytetrahydropyrans and 2-acetoxytetrahydropyran, and barrier to ring inversion

The 13C nuclear magnetic resonance data of a series of 2-(4-substituted-phenoxy)tetrahydropyrans at 156 K and in CF2Br2 and CHFCl2 solvents show that the axial preference increases with electron withdrawal in the aryloxy group: from 79 percent (ΔG0E->A = -0.4 kcal mol-1) (4-OCH3) to 90 percent (ΔG0E->A = -0.7 kcal mol-1) (4-NO2) in CF2Br2.The axial preference (anomeric effect) is smaller in the more polar CHFCl2 solvent, as expected, and the substituent effect is smaller also: change in ΔG0E->A from -0.3 (4-OCH3) to -0.5 (4-NO2) kcal mol-1.However, the axial preference of 2-acetoxytetrahydropyran is shown to be smaller than that of 2-phenoxytetrahydropyran in CF2Br2 solvent although the acetoxy group is expexted to be more electronegative than the phenoxy group.Furthermore, the polarity of the solvent has no effect on the conformational equilibrium of 2-acetoxytetrahydropyran.The results are interpreted in terms of both orbital and electrostatic interactions.The ring-inversion barrier of 2-alkoxy and 2-aryloxytetrahydropyrans, determined by the temperature-coalescence method, is lower than that of tetrahydropyran by about 1.5 kcal mol-1.