18951-45-6

Upstream product

• 17555-94-1 (E)-4'-methoxy-4-methylstilbene 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 2628-17-3 4-Vinylphenol 
• 540-38-5 p-Iodophenol 
• 624-31-7 4-tolyl iodide 
• 7400-08-0 p-Coumaric Acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 99-94-5 p-Toluic acid 
• 622-47-9 4-tolylacetic acid 
• 321155-43-5 (E)-β-(2-pyridyldimethylsilyl)-4-methylstyrene 

Downstream Products

• 184017-91-2 4-methoxy-N-(4-methylbenzyl)aniline 
• 73351-21-0 4-(((4-methoxyphenyl)amino)methyl)phenol 
• 30669-07-9 4-methoxy-N-[(4-methylphenyl)methylidene]aniline 
• 3230-50-0 4-(4-hydroxyphenyl)-N-(4-methoxyphenyl)imine 

Relevant academic research and scientific papers

Structural information from methyl rotors: Methyl torsional barriers in p-hydroxy-p′-methyl-t-stilbene and its water complexes

The barriers to internal rotation for the methyl group in p-hydroxy-p′-methyl-t-stilbene and its one- and two-water complexes are reported. The jet-cooled fluorescence excitation spectra of these species are also presented. The excitation spectrum of both

Synthesis and cytotoxic effects on pancreatic cancer cells of resveratrol analogs

In this study, a series of resveratrol analogs was synthesized and the effects on the viability of pancreatic cancer cell lines were evaluated. The new molecules were designed by removing the 3- and 5-OH groups of resveratrol, and by incorporating other s

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

Chemo-enzymatic synthesis of (: E)-2,3-diaryl-5-styryl- trans -2,3-dihydrobenzofuran-based scaffolds and their in vitro and in silico evaluation as a novel sub-family of potential allosteric modulators of the 90 kDa heat shock protein (Hsp90)

Herein we propose a facile, versatile and selective chemo-enzymatic synthesis of substituted (E)-2,3-diaryl-5-styryl-trans-2,3-dihydrobenzofurans based on the exploitation of the laccase-mediated oxidative (homo)coupling of (E)-4-styrylphenols. Thanks to this novel synthetic strategy, a library of benzofuran-based potential allosteric activators of the Heat shock protein 90 (Hsp90) was easily prepared. Moreover, considering their structural analogies to previously reported allosteric modulators, the sixteen new compounds synthesized in this work were tested in vitro for their potential stimulatory action on the ATPase activity of the molecular chaperone Hsp90. Combining experimental and computational results, we propose a mechanism of action for these compounds, and expand the structure-activity relationship (SAR) information available for benzofuran-based Hsp90 activators.

PPARα agonists based on stilbene and its bioisosteres: Biological evaluation and docking studies

A new series of gemfibrozil analogues conjugated with trans-stilbene were synthesized and evaluated with the aim of developing new PPARα agonists. The phenyls of stilbene were modified by introducing substituents in the ortho or para position and only the

Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: A protecting-group economic synthesis of phenolic stilbenes

4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior. The Royal Society of Chemistry 2013.

Tandem heck/decarboxylation/heck strategy: Protecting-group-free synthesis of symmetric and unsymmetric hydroxylated stilbenoids

Ride the (micro)wave: The title strategy has been developed for the synthesis of various symmetric or unsymmetric hydroxylated stilbenoids utilizing 4-halophenols and acrylic acid as coupling partners (see scheme; DMA=N,N-dimethylacetamide, MW=microwave). Protecting groups are not necessary and a single palladium catalyst is used. Copyright

Radical-scavenging activity and mechanism of resveratrol-oriented analogues: Influence of the solvent, radical, and substitution

(Chemical Equation Presented). Resveratrol (3,5,4′-trihydroxy-trans- stilbene, 3,5,4′-THS) is a well-known natural antioxidant and cancer chemopreventive agent that has attracted much interest in the past decade. To find a more active antioxidant and investigate the antioxidative mechanism with resveratrol as the lead compound, we synthesized 3,5-dihydroxy-trans-stilbene (3,5-DHS), 4-hydroxy-trans-stilbene (4-HS) 3,4-dihydroxy-trans-stilbene (3,4-DHS), 4,4′-dihydroxy-trans-stilbene (4,4′-DHS), 4-hydroxy-3-methoxy-trans-stilbene (3-MeO-4-HS), 4-hydroxy-4′-methoxy- trans-stilbene (4′-MeO-4-HS), 4-hydroxy-4′-methyl-trans-stilbene (4′-Me-4-HS), 4-hydroxy-4′-nitro-trans-stilbene (4′-NO 2-4-HS), and 4-hydroxy-4′-trifluoromethyl-trans-stilbene (4′-CF3-4-HS). The radical-scavenging activity and detailed mechanism of resveratrol and its analogues (ArOHs) were investigated by the reaction kinetics with galvinoxyl (GO?) and 2,2-diphenyl-1- picrylhydrazyl (DPPH?) radicals in ethanol and ethyl acetate at 25°C, using UV-vis spectroscopy. It was found that the reaction rates increase with increasing the electron-rich environment in the molecules, and the compound bearing o-dihydroxyl groups (3,4-DHS) is the most reactive one among the examined resveratrol analogues. The effect of added acetic acid on the measured rate constant for GO?-scavenging reaction reveals that in ethanol that supports ionization solvent besides hydrogen atom transfer (HAT), the kinetics of the process is partially governed by sequential proton loss electron transfer (SPLET). In contrast to GO?, DPPH ? has a relatively high reduction potential and therefore enhances the proportion of SPLET in ethanol. The relatively low rate constants for the reactions of ArOHs with GO? or DPPH? in ethyl acetate compared with the rate constants in ethanol prove that in ethyl acetate these reactions occur primarily by the HAT mechanism. The contribution of SPLET and HAT mechanism depends on the ability of the solvent to ionize ArOH and the reduction potential of the free radical involved. Furthermore, the fate of the ArOH-derived radicals, i.e., the phenoxyl radicals, was investigated by the oxidative product analysis of ArOHs and GO? in ethanol. The major products were dihydrofuran dimers in the case of resveratrol, 4,4′-DHS, and 4-HS and a dioxane-like dimer in the case of 3,4-DHS. It is suggested from the oxidative products of these ArOHs that the hydroxyl group at the 4-position is much easier to subject to oxidation than other hydroxyl groups, and the dioxane-like dimer is formed via an o-quinone intermediate.

A short and efficient synthetic approach to hydroxy (E)-stilbenoids via solid-phase cross metathesis

Solid-phase cross metathesis of supported styrenyl ether with styrene derivatives afforded stilbenoids in high yields with complete (E)-selectivity, and this approach could be readily applied for a facile synthesis of a biologically important natural product, resveratrol.

Diversity-oriented synthesis of multisubstituted olefins through the sequential integration of palladium-catalyzed cross-coupling reactions. 2-Pyridyldimethyl(vinyl)silane as a versatile platform for olefin synthesis

A novel strategy for the diversity-oriented synthesis of multisubstituted olefins, where 2-pyridyldimethyl (vinyl)silane functions as a versatile platform for olefin synthesis, is described. The palladium-catalyzed Heck-type coupling of 2-pyridyldimethyl(vinyl)silanes with organic iodides took place in the presence of Pd2-(dba) 3/tri-2-furylphosphine catalyst to give β-substituted vinylsilanes in excellent yields. The Heck-type coupling occurred even with α- and β-substituted 2-pyridyldimethyl(vinyl)silanes. The one-pot double Heck coupling of 2-pyridyldimethyl(vinyl)silane took place with two different aryl iodides to afford β,β-diarylated vinylsilanes in good yields. The palladium-catalyzed Hiyama-type coupling of 2-pyridyldimethyl(vinyl)silane with organic halides took place in the presence of tetrabutylammonium fluoride to give di- and trisubstituted olefins in high yields. The sequential integration of Heck-type (or double Heck) coupling and Hiyama-type coupling produced the multisubstituted olefins in regioselective, stereoselective, and diversity-oriented fashions. Especially, the one-pot sequential Heck/Hiyama coupling reaction provides an extremely facile entry into a diverse range of stereodefined multisubstituted olefins. Mechanistic considerations of both Heck-type and Hiyama-type coupling reactions are also described.