847-83-6Relevant academic research and scientific papers
(4-Methoxyphenyl)diphenylmethanol, an unusual tetramer containing a D[R] pattern of hydrogen bonds, and tris(2-methoxyphenyl)methanol
Patterson, Iain L. J.,Glidewell, Christopher,Ferguson, George
, p. 1970 - 1974 (1998)
(4-Methoxyphenyl)diphenylmethanol (C20H18O2) crystallizes with two independent molecules; the molecules are linked by O-H...O hydrogen bonds into centrosymmetric tetramers in which two molecules form a cyclic R22(16) motif from which the other two are pendant, giving a D33(11)[R22(16)] pattern. In tris(2-methoxyphenyl)methanol (C22H22O4) the hydroxy H atoms are disordered over two sites; whichever site is occupied, an intramolecular O-H...O hydrogen bond is formed with a methoxy O atom.
Expeditious and practical synthesis of tertiary alcohols from esters enabled by highly polarized organometallic compounds under aerobic conditions in Deep Eutectic Solvents or bulk water
Quivelli, Andrea F.,D'Addato, Giovanna,Vitale, Paola,García-álvarez, Joaquín,Perna, Filippo M.,Capriati, Vito
, (2021/01/18)
An efficient protocol was developed for the synthesis of tertiary alcohols via nucleophilic addition of organometallic compounds of s-block elements (Grignard and organolithium reagents) to esters performed in the biodegradable choline chloride/urea eutectic mixture or in water. This approach displays a broad substrate scope, with the addition reaction proceeding quickly (20 s reaction time) and cleanly, at ambient temperature and under air, straightforwardly furnishing the expected tertiary alcohols in yields of up to 98%. The practicability of the method is exemplified by the sustainable synthesis of some representative S-trityl-L-cysteine derivatives, which are a potent class of Eg5 inhibitors, also via telescoped one-pot processes.
An Efficient Ga(OTf)3/Isopropanol Catalytic System for Direct Reduction of Benzylic Alcohols
Sai, Masahiro
supporting information, p. 4330 - 4335 (2018/10/15)
This study aims to report the first gallium-catalyzed direct reduction of benzylic alcohols using isopropanol as a reductant. The reaction proceeds via gallium catalyst-assisted hydride transfer of the in situ-generated benzylic isopropyl ether. The method generates only water and acetone as byproducts and thus provides an atom-economic and environmentally friendly approach to the synthesis of di- and triarylmethanes, which are important substructures in various bioactive compounds and functional materials. (Figure presented.).
MELANIN PRODUCTION INHIBITOR
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Paragraph 0230 - 0238, (2015/12/17)
Disclosed is a melanin production inhibitor which has an excellent inhibitory activity on the production of melanin and is highly safe. The melanin production inhibitor is represented by general formula (1) (excluding clotrimazole) and/or a pharmacologically acceptable salt thereof. In the formula, A1, A2 and A3 are independently selected from a hydrogen atom, an aryl group which may have a substituent, and an aromatic heterocyclic group which may have a substituent. At least one of A1, A2 and A3 is selected from the aryl group and the aromatic heterocyclic group, the total number of carbon atoms contained in A1, A2 and A3 is 6 to 50 and, when at least two of A1, A2 and A3 represent the aryl groups or the aromatic heterocyclic groups, the adjacent two aryl or aromatic heterocyclic groups may be bound to each other via an alkyl chain or an alkenyl chain to form a ring; m represents an integer of 0 to 2; X represents a hetero atom, a hydrogen atom, or a carbon atom; R1 and R2 are independently selected from a hydrogen atom and an oxo group. When one of R1 and R2 is an oxo group, the other is not present. R3 is selected from a hydrogen atom, and a C1-8 hydrocarbon group in which one or some of hydrogen atoms or carbon atoms may be substituted by a hetero atom or hetero atoms. The number of R3's present in the compound corresponds to X and, when two or more R3's are present, the R3's are independently present and the adjacent two R3's may be bound to each other to form, together with X, a ring, and the terminal of R3 may be bound to a carbon atom to which A1, A2 and A3 are bound, thereby forming a ring.
Oxidative gold catalysis meets photochemistry - Synthesis of benzo[a]fluorenones from diynes
N?sel, Pascal,Moghimi, Setareh,Hendrich, Christoph,Haupt, Marten,Rudolph, Matthias,Rominger, Frank,Hashmia, A. Stephen K.
supporting information, p. 3755 - 3760 (2015/01/09)
Diynes bearing one terminal and one triarylmethylsubstituted alkyne were converted into complex benzofluorenone derivatives via a one-pot process involving a gold-catalyzed step followed by a photocyclization/oxidation. In the first step an Noxide was used to position-selectively generate an a-oxo carbenoid at the terminal alkyne which after a regioselective 1,6-carbene transfer along the tethered tritylalkyne and a subsequent aryl 1,2-shift furnished tetraphenylethylene-like derivatives. These intermediates were successfully transformed to fluorenones via oxidative photocyclization.
METHOD OF INHIBITING APOLIPOPROTEIN-E EXPRESSION COMPRISING ADMINISTERING A TRIARYLMETHYL AMINE COMPOUND
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Paragraph 0047-0048, (2014/02/15)
This invention offers an effective method of inhibiting the expression of apolipoprotein E by mammalian cells. Apolipoprotein E is a protein that plays a significant role in the development of Alzheimer's Disease in humans. The method comprises administering an effective amount of a triarylmethyl amine compound having the general formula: wherein the R1 group may comprise acyclic amines and aliphatic amines. The R2 group may comprise one of three aryl varieties: aryl, substituted aryl, or heterocycle. Triarylamine compounds inhibit apolipoprotein E expression in mammalian cells. In one aspect of the invention the mammalian cells may be human cells, and more specifically may be human brain cells.
Acid-catalysed hydrolysis of trityl derivatives in strongly acidic aqueous media
Canle L., Moises,Maskill, Howard
supporting information, p. 1016 - 1022 (2014/01/06)
The kinetics of hydrolysis (deamination or dealcoholation) of tritylamines and 2,2,2-trifluoroethyl ethers and their corresponding 4-methoxy, 4,4′-dimethoxy-, and 4,4′,4″-trimethoxy-substituted analogues in aqueous solutions up to 3.5 mol · dm-3 in strong acid have been investigated at constant ionic strength. In all cases, acid-catalysed hydrolytic processes have been observed, with finite reactivity at [H 3O+] = 0. Strong upward curvature has been observed for kobs versus [HClO4]. Analysis of this dependence in terms of the HR acidity function and the X0 excess acidity scale allow explanation of the observed behaviour in terms of the increasing differences between concentrations and activities of the various species involved in the processes, including water, for which the activity coefficient strongly diverges from its standard state value as the acidity increases. This analysis has shown that, by taking account of the effect of the ionic strength, the same mechanistic models proposed for mildly acidic solutions are valid in more highly concentrated acid media. These comprise (i) protonation of the trityl ether followed by C-O bond heterolysis to give a carbenium ion-alcohol (ion-molecule) pair which can separate, and (ii) C-N bond heterolysis of the protonated tritylamine to give a carbenium ion-amine (ion-molecule) pair followed by separation of the fragments or protonation of the amine and subsequent separation of the ions. Each separated (substituted) trityl carbenium ion, regardless of its provenance, is invariably captured by a solvent molecule (water). Copyright 2013 John Wiley & Sons, Ltd. Strong upward curvatures observed for kobs versus [H3O+] kinetics results in the hydrolysis of tritylamines and trityl ethers in strongly acidic aqueous solutions are entirely understandable as medium effects and accurately described in terms of excess acidities. The mechanisms previously proposed for mild acidic conditions have been generalized to more strong acid media. Copyright
Near-ambient temperature halogen-lithium exchange of p-bromoanisole and related substrates: Flow/batch studies
Slocum,Reinscheld, Thomask.,Austin, Nickd.,Kusmic, Damir,Whitley, Paule.
experimental part, p. 2531 - 2536 (2012/09/22)
With the advent of flow chemistry, the norm has been reactions executed on the laboratory scale with flow rates of only a few mL/min. We bring to the community's attention our investigation of the halogen-lithium (X-Li) exchange in a continuous flow reactor, the Synthetron. This novel reactor is capable of orders of magnitude greater rates of flow than current microreactors. This paper details a problematic X-Li exchange using our promoted hydrocarbon media formulated batch studies as well as the comparative derived flow studies. All of these studies have the additional feature of being performed at ambient or near-ambient temperatures. From the initial discoveries of Wittig and Gilman in the late 1930s, it has been known that X-Li exchange of p-bromoanisole (p-BrA) is plagued by a secondary ortho-lithiation. Fine-tuning of promoted hydrocarbon media batch studies can increase the ratio of p-LiA/o-Li-p-BrA; results from the Synthetron studies afford a much superior ratio of >100:1. Gram quantities of derivatives from this exchange (employing two reactors) can be prepared in a few seconds. Rationales for these observations will be presented as well as initial studies and discussion for bromobenzene (PhBr), m-bromoanisole (m-BrA), and p-iodoanisole (p-IA). Georg Thieme Verlag Stuttgart · New York.
Design, synthesis and identification of a new class of triarylmethyl amine compounds as inhibitors of apolipoprotein e production
Singh, Mandeep,Schott, Jason T.,Leon, Martin A.,Granata, Robert T.,Dhah, Harkiran K.,Welles, Jason A.,Boyce, Michelle A.,Oseni-Olalemi, Hafeez S.,Mordaunt, Charles E.,Vargas, Anthony J.,Patel, Nilay V.,Maitra, Santanu
, p. 6252 - 6255 (2012/10/29)
We have identified a new class of triarylmethyl amine compounds that can inhibit apolipoprotein E (apoE) production. ApoE is a cholesterol- and lipid-carrier protein implicated in aging, atherosclerosis, Alzheimer's Disease (AD), and other neurological and lipid-related disorders. Attenuation of apoE production is generally considered to be of therapeutic value. A majority of the apoE in the brain is produced by astrocytes. Here, we describe the design, synthesis, and biological screening of a small library of compounds that led to the identification of four triarylmethyl amines as potent inhibitors of apoE production in CCF-STTG1 astrocytoma cells.
Electrophilicity versus electrofugality of tritylium ions in aqueous acetonitrile
Horn, Markus,Mayr, Herbert
supporting information; scheme or table, p. 7478 - 7487 (2010/08/20)
First-order rate constants kw for the reactions of a series of donorsubstituted triphenylmethylium (tritylium) ions with water in aqueous acetonitrile have been determined photometrically at 20°C using stopped-flow and laser-flash techniques. T
