70945-85-6

Upstream product

• 98-54-4 para-tert-butylphenol 
• 99-90-1 para-bromoacetophenone 
• 99-91-2 para-chloroacetophenone 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 99-93-4 4-Hydroxyacetophenone 
• 100-19-6 (4-nitrophenyl)ethanone 
• 13329-40-3 4-Iodoacetophenone 
• 403-42-9 1-(4-fluorophenyl)ethanone 

Downstream Products

• 39064-93-2 4-(4-(tert-butyl)phenoxy)phenol 

Relevant academic research and scientific papers

Isothiouronium salts as useful and odorless intermediates for the synthesis of thiaalkylimidazolium ionic liquids

A simple and odorless route for the synthesis of monocationic and dicationic thiaalkylimidazolium ionic liquids (ILs) is reported. Our approach starts with the selective monoalkylation of dihalogenated substrates by methylimidazole derivatives, followed b

Diaryl Ether Formation Merging Photoredox and Nickel Catalysis

Photoredox and Ni catalysis are combined to produce diaryl ethers under mild conditions. A broad range of aryl halides and phenol derivatives are cross-coupled in the presence of a readily available organic photocatalyst and NiBr2(dtbpy). Symmetrical diaryl ethers have also been directly obtained from aryl bromides in the presence of water. Mechanistic investigations support the involvement of Ni(0) species at the outset of the reaction and a Ni(II)/Ni(III)-photocatalyzed single electron transfer process preceding the productive C(sp2)-OAr reductive elimination.

Nickel-Catalyzed Etherification of Phenols and Aryl Halides through Visible-Light-Induced Energy Transfer

Notwithstanding some progress in nickel-catalyzed etherification of alkanols and arylhalides, the ability of such a Ni-catalyzed transformation employing phenols to diaryl ethers is unsuccessful due to phenolates with much lower reduction potentials, which suppress the oxidation of nickel(II) intermediates into requisite Ni(III) species. We herein report visible-light-initiated, nickel-catalyzed O-arylation of phenols with arylhalides using t-BuNH(i-Pr) as the base and thioxanthen-9-one as the photosensitizer under visible light. This photocoupling exhibits a broad substrate scope.

Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors

Protein tyrosine phosphatase 1B (PTP1B) has been considered as a validated biological target for type 2 diabetes treatment, but past endeavors to develop inhibitors of PTP1B into drugs have been unsuccessful. Two challenging aspects are selective inhibition and cell permeability. A structure-based strategy was employed to develop uncharged bromophenols as a new series of PTP1B inhibitors. The most potent compound 22 (LXQ46) inhibited PTP1B with an IC50 value of 0.190 μM, and showed remarkable selectivity over other protein tyrosine phosphatases (PTPs, 20–200 folds). In the SPR study, increasing concentrations of compound 22 led to concentration-dependent increases in binding responses, indicating that compound 22 could bind to the surface of PTP1B via noncovalent means. By treating insulin-resistant C2C12 myotubes with compound 22, enhanced insulin and leptin signaling pathways were observed. Long-term oral administration of compound 22 reduced the blood glucose level of diabetic BKS db mice. The glucose tolerance tests (OGTT) and insulin tolerance tests (ITT) in BKS db mice showed that oral administration of compound 22 could increase insulin sensitivity. In addition, long-term oral administration of compound 22 could protect mice from obesity, which was not the result of toxicity. Our pharmacokinetics results from the rat-based assays showed that orally administered compound 22 was absorbed rapidly from the gastrointestinal tract, extensively distributed to the tissues, and rapidly eliminated from the body. All these results indicate that compound 22 could serve as a qualified agent to treat type II diabetes.

Design, synthesis and biological evaluation of uncharged catechol derivatives as selective inhibitors of PTP1B

Protein tyrosine phosphatases 1B (PTP1B) is a promising and validated therapeutic target to effectively treat T2DM and obesity. However, the development of charged PTP1B inhibitors was restricted due to their low cell permeability and poor bioavailability. Based on active natural products, two series of uncharged catechol derivatives were identified as PTP1B inhibitors by targeting a secondary aryl phosphate-binding site as well as the catalytic site. The most potent inhibitor 22 showed an IC50 of 0.487?μM against PTP1B and strong selectivity (27-fold) over TCPTP. Kinetic studies were also performed that 22 act as a competitive PTP1B inhibitor. The treatment of C2C12 myotubes with 22 markedly increased the phosphorylation levels of IRβ, Akt and IRS1 phosphorylation. The similarity of its action profiling with that produced by insulin suggested its potential as a new non-insulin-dependent drug candidate.

Palladium-on-Carbon-Catalyzed Coupling of Nitroarenes with Phenol: Biaryl Ether Synthesis and Evidence of an Oxidative-Addition-Promoted Mechanism

Nucleophilic substitution in nitroarenes to form biaryl ethers is of fundamental importance in organic synthesis. Under non-catalytic conditions, this can occur if highly activated nitroarenes are used or if the nucleophile is activated by a strong stoichiometric base. We established a new method involving the use of a ligand-free palladium-on-carbon (Pd/C) catalyst for the cross-coupling of activated nitroarenes with relatively non-nucleophilic phenol derivatives, including naphthol, in the absence of harsh bases. Control experiments, hot filtration, the three-phase test, and inductively coupled plasma atomic emission spectroscopy analysis revealed that the catalysis proceeded through an usual oxidative addition step of the nitroarene to Pd/C, which resulted in the release of active palladium particles having extremely high catalytic activity. DFT calculations revealed the origin of the selectivity of the activated nitroarenes.

SAR-based optimization of a 4-quinoline carboxylic acid analogue with potent antiviral activity

It is established that drugs targeting viral proteins are at risk of generating resistant strains. However, drugs targeting host factors can potentially avoid this problem. Herein, we report structure-activity relationship studies leading to the discovery

Copper-in-charcoal (Cu/C) promoted diaryl ether formation

(Chemical Equation Presented) Copper impregnated into charcoal efficiently catalyzes cross-couplings between aryl bromides and phenols. The etherifications were conveniently promoted by microwave heating.

Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers

A general method for the palladium-catalyzed formation of diaryl ethers is described. Electron-rich, bulky aryldialkylphosphine ligands, in which the two alkyl groups are either tert-butyl or 1-adamantyl, are the key to the success of the transformation. A wide range of electron-deficient, electronically neutral and electron-rich aryl bromides, chlorides, and triflates can be combined with a variety of phenols with the use of sodium hydride or potassium phosphate as base in toluene at 100 °C. The bulky yet basic nature of the phosphine ligand is thought to be responsible for increasing the rate of reductive elimination of the diaryl ether from palladium.

A convenient method for the preparation of 4-aryloxyphenols

A convenient method for the preparation of 4-aryloxyphenols via the homologation of preformed phenols is described. Condensation of various 4-substituted phenols with either 4-fluorobenzaldehyde (8) or 4-fluoroacetophenone (9) yielded the corresponding 4-aryl-oxybenzaldehydes, 10, and acetophenones, 11, in 70-93% yield. Baeyer-Villiger oxidation of these materials with 3-chloroperoxybenzoic acid (MCPBA) yielded the corresponding 4-formyloxy and 4-acetoxyphenyl ethers which were hydrolyzed without purification to the desired 4-aryloxyphenols 12 in 72-94% yield. Both 4-fluorobenzaldehyde (8) and 4-fluoroacetophenone (9) are synthetically equivalent to the a4 umpoled synthon 6. Extension of this methodology of the preparation of 4,4'-[arylbis(oxy)]bisphenols from aromatic diols is also described. Condensation of various aromatic diols with 8 or 9 yielded the corresponding 4,4'-[arylbis(oxy)]bisbenzaldehydes 15 and acetophenones 16 in 71-89% yield. Baeyer-Villiger oxidation of these compounds with MCPBA yielded the desired 4,4'-[arylbis(oxy)]bisphenyl bisformates 17 and bisacetates 18 in 67-84% yield. Hydrolysis of these compounds afforded the desired 4,4'-[arylbis(oxy)bisphenols 19 in 70-91% yield.