4254-67-5

Usage

Preparation

Obtained by reaction of bromine with 4-benzyloxyacetophenone in methanol in the presence of concentrated hydrochloric acid at 0–5° for 1 h, then at r.t. for another 1 h (90%).

InChI:InChI=1/C15H13BrO2/c16-10-15(17)13-6-8-14(9-7-13)18-11-12-4-2-1-3-5-12/h1-9H,10-11H2

Upstream product

• 54696-05-8 4'-benzyloxy-acetophenone 
• 123-91-1 1,4-dioxane 
• 100-44-7 benzyl chloride 
• 99-90-1 para-bromoacetophenone 
• 100-51-6 benzyl alcohol 
• 36438-63-8 1-(4-[benzyloxy]phenyl)ethan-1-ol 
• 84284-70-8 [4-(benzyloxy)phenyl]acetylene 
• 2491-38-5 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone 
• 100-39-0 benzyl bromide 
• 92850-54-9 2-amino-1-(4-benzyloxy-phenyl)-ethanone 
• 15028-44-1 DL-phenylalanine methyl ester 
• 7789-45-9 copper(II)bromide 
• 99-93-4 4-Hydroxyacetophenone 

Downstream Products

• 72294-65-6 1-(4-benzyloxy-phenyl)-2-morpholin-4-yl-ethanone 
• 36611-41-3 4-{2-[2-Hydroxy-2-(4-hydroxy-phenyl)-ethylamino]-ethoxy}-benzamide 
• 36611-40-2 2-[4-(2-{Benzyl-[2-(4-benzyloxy-phenyl)-2-hydroxy-ethyl]-amino}-ethoxy)-phenyl]-acetamide 
• 47369-95-9 N-(2-{2-[2-Hydroxy-2-(4-hydroxy-phenyl)-ethylamino]-ethoxy}-phenyl)-acetamide 
• 36611-53-7 N-(4-{2-[2-Hydroxy-2-(4-hydroxy-phenyl)-ethylamino]-ethoxy}-benzyl)-acetamide 
• 36665-76-6 N-(4-{2-[2-Hydroxy-2-(4-hydroxy-phenyl)-ethylamino]-ethoxy}-phenyl)-methanesulfonamide 
• 94402-91-2 ethyl trans-3-(4-benzyloxybenzoyl)glycidate 
• 146698-61-5 4-(4-Benzyloxyphenyl)imidazole 
• 93035-37-1 1-(4-benzyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanone 
• 56122-35-1 1-(4-(benzyloxy)phenyl)-2-(2-methoxyphenoxy)ethan-1-one 
• 217302-87-9 2-(4-benzyloxyphenyl)-1-ethylindolizine 
• 4195-25-9 2-amino-1-(4-benzyloxyphenyl)ethanone hydrochloride 

Relevant academic research and scientific papers

A responsive europium(III) chelate that provides a direct readout of pH by MRI

A europium(III) DO3A-tris(amide) complex is reported for imaging pH by MRI using ratiometric chemical exchange saturation transfer (CEST) principles. Deprotonation of a single phenolic proton between pH 6 and 7.6 results in an ～5 ppm shift in the water ex

Stereoselective Formation of β-O-4 Structures Mimicking Softwood Lignin Biosynthesis: Effects of Solvent and the Structures of Quinone Methide Lignin Models

p-Quinone methide (QM) is formed as an intermediate during lignin biosynthesis. The aromatization of the QM by the attack of a nucleophile at the α-position of its side chain generates a phenolic hydroxy group in a growing polymer and creates stereoisomeric forms in the side chain. A series of β-O-4-aryl ether QMs was reacted with water at 25 °C to replicate the formation of p-hydroxyphenyl (H) and guaiacyl (G) β-O-4 structures in plant cell walls. Water addition occurred in 3-methoxy-substituted QMs (G-type QMs) with half-lives (t1/2) between 13 and 15 min, at pH 7, in 50% water solution (dioxane-water, 1:1). The rate increased as the water concentration increased to 99% (t1/2, 1.2-1.4 min). Similar solvent effects were observed for more reactive nonsubstituted QMs (H-type QMs with t1/2 of 1/2 of the H-type QMs was shorter than that of the G-type QMs under every solvent condition. Upon increasing the water concentration, the variation in the erythro/threo ratios of the four dimeric β-O-4 products increased. Interestingly, the effect of pH on the stereopreference, which was observed in 50% water solution, was small and became imperceptible as the water concentration increased to 99%, suggesting that the effect of the solvent, as well as the effect of the pH, plays an important role in understanding the reaction conditions in cell walls during lignin biosynthesis. The threo isomer was preferentially formed in the four dimeric β-O-4 structures, which is inconsistent with the structural features of compression wood lignin rich in H-units. However, the erythro-selective formation was attained in an H-type QM at every pH studied (pH 3.5-7) by introducing a biphenyl structure into the β-etherified ring moiety.

Photophysics of Perylene Diimide Dianions and Their Application in Photoredox Catalysis

The two-electron reduced forms of perylene diimides (PDIs) are luminescent closed-shell species whose photochemical properties seem underexplored. Our proof-of-concept study demonstrates that straightforward (single) excitation of PDI dianions with green

Benzoic acid resin (BAR): a heterogeneous redox organocatalyst for continuous flow synthesis of benzoquinones from β-O-4 lignin models

A polymer-bound organocatalyst for Baeyer-Villiger reaction and phenol oxidation under continuous flow conditions is described for the first time.BARhas revealed two catalytic activities that enabled the generation of a novel approach for the synthesis of benzoquinones from β-O-4 lignin models in a one-pot protocol. High catalytic activities (yields up to 98%), selectivities, recyclability and productivity were achieved.

Convergent Total Synthesis of Lamellarins and Their Congeners

A convergent total synthesis of lamellarins S and Z is described. The synthesis features a halogen dance of an easily accessible α,β-dibromopyrrole promoted by an ester moiety. The resultant β,β′-dibromopyrrole undergoes a ligand-controlled Suzuki-Miyaura coupling to provide a range of diarylated pyrrole derivatives. The established synthetic method was also applicable to the synthesis of ningalin B and lukianols A and B.

Pd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors

The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alcohol-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.

BETA-HYDROXYETHYLAMINES FOR USE IN THE TREATMENT OR PREVENTION OF NON-ALCOHOLIC FATTY LIVER DISEASES

There is herein provided a compound of formula (I) or a pharmaceutically acceptable salt thereof, for use in the treatment of a non-alcoholic fatty liver disease (NAFLD), such as non-alcoholic steatohepatitis (NASH), wherein X, R1, R2, R3 and n have meanings as provided in the description.

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.

CHIRAL BETA-HYDROXYETHYLAMINES AND THEIR USE IN THE TREATMENT OF HYPERGLYCEMIA

There is herein provided a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein X, R1, R 2, R 3, R 4 and n have meanings as provided in the description.

Vinylethylene Carbonates as α,β-Unsaturated Aldehyde Surrogates for Regioselective [3 + 3] Cycloaddition

Herein, we report a novel stepwise addition-controlled ring size method, to access tetrahydropyrimidines through an operationally simple [3 + 3] cycloaddition of vinylethylene carbonates with triazinanes. Interestingly, we could also use this method for a [3 + 3] oxidative cycloaddition, which allows the facile synthesis of polysubstituted terphenyls under mild conditions. Mechanistic studies suggest that vinylethylene carbonates could generate α,β-unsaturated aldehydes as 3-carbon synthons for cycloaddition via a combination process of Pd-catalyzed decarboxylation and β-H elimination.