93022-30-1

Upstream product

• 674368-06-0 4-[(Z)-2-phenylethenyl]phenyl acetate 
• 3839-46-1 stilben-4-ol 
• 108-24-7 acetic anhydride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-44-7 benzyl chloride 
• 878-00-2 4-formylphenyl acetate 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 100-42-5 styrene 
• 33527-94-5 4-acetoxyiodobenzene 
• 75-36-5 acetyl chloride 
• 540-38-5 p-Iodophenol 
• 108-86-1 bromobenzene 
• 2628-16-2 p-acetoxystyrene 
• 114-70-5 sodium phenylacetate 

Downstream Products

• 1357581-69-1 (trans-2,4-diphenylcyclobutane-1,3-diyl)dibenzene-4,1-diyl diacetate 
• 1357581-71-5 (cis-2,4-diphenylcyclobutane-1,3-diyl)dibenzene-4,1-diyl diacetate 
• 1357581-66-8 [(1RS,2SR,3RS,4SR)-3,4-diphenylcyclobutane-1,2-diyl]dibenzene-4,1-diyl diacetate 
• 674368-06-0 4-[(Z)-2-phenylethenyl]phenyl acetate 
• 6554-98-9 trans-4-Hydroxystilbene 

Relevant academic research and scientific papers

METHODS OF ARENE ALKENYLATION

The present disclosure provides for a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. For example, the present disclosure provides for method of making arenes or substituted arenes, in particular stilbene and stilbene derivatives, from a reaction of an optionally substituted arene and/or optionally substituted styrene. The reaction includes a Rh catalyst or Rh pre-catalyst material and an oxidant, where the Rh catalyst or Rh catalyst formed Rh pre-catalyst material selectively functionalizes CH bond on the arene compound (e.g., benzene or substituted benzene).

Ionic liquid-mediated benzoyl transfer-coupling in the Suzuki and Sonogashira reactions and aryl transfer-coupling by decarbonylative Heck reaction, using N-Benzoyl-saccharin (NBSac) as reagent

The efficacy of N-benzoyl-saccharin (NBSac) as reagent for selective benzoyl transfer-coupling in the Suzuki reaction in BMIM-IL/[PAIM][NTf2] as solvent/base, and in the Sonogashira reaction employing guanidinium-IL (GIL) as solvent, are demonstrated. Decarbonylative aryl transfer-coupling occurs in the Heck reaction employing GIL as solvent. The reactions are catalyzed by Pd(OAc)2 or NiCl2(dppp), are performed under mild conditions in good yields, and have the potential for recycling/reuse of the IL solvent. Collectively, these methods provide facile access to diverse libraries of diarylketones, keto-ethynes and diaryl-ethenes.

Galloyl esters of trans-stilbenes are inhibitors of FASN with anticancer activity on non-small cell lung cancer cells

Fatty acid synthase (FASN) is a lipogenic enzyme that is selectively upregulated in malignant cells. There is growing consensus on the oncogenicity of FASN-driven lipogenesis and the potential of FASN as a druggable target in cancer. Here, we report the synthesis and FASN inhibitory activities of two novel galloyl esters of trans-stilbene EC1 and EC5. Inhibition of FASN was accompanied by a loss in AKT activation and profound apoptosis in several non-small cell lung cancer (NSCLC) cells at the growth inhibitory concentrations of EC1 and EC5. Both FASN and phospho-AKT levels were concurrently downregulated. However, addition of a lipid concentrate to the treated cells reinstated cell viability and reversed the loss of FASN and AKT protein levels, thus recapitulating the causal relationship between FASN inhibition and the loss in cell viability.

Stereodivergent Alkyne Reduction by using Water as the Hydrogen Source

A homogeneous Pd-catalyzed stereodivergent reduction of alkynes to Z and E alkenes by using H2O as the H2 source is presented. Mediated by a diboron reagent, the transfer hydrogenation has been accomplished to yield the desired geometrical isomer by rational ligand selection. The switchable stereoselectivity achieved using simple phosphine ligands is generally excellent. D2O has also been used as a D2 source for synthesizing the corresponding deuterated olefins. Supported by a gram-scale synthesis, the reaction can easily be scaled up making it an efficient way to prepare alkenes commercially as well. Mechanistic studies suggest formation of H?PdL2?OAc as the crucial step leading to the presence of two pathways involving H?Pd?B(OR)2 and molecular H2 as active intermediates.

A nitrogen and sulphur functionalized graphene oxide-palladium nanoparticle hybrid catalyst for an efficient Heck coupling

A nanocomposite comprised of Pd nanoparticles supported on chemically modified graphene (CMG) has been fabricated. Morphological and chemical characterization of the CMG-PdNP heterostructure has been carried out using PXRD, FTIR, Raman, XPS, TEM, SEM, EDX, and ICP-MS studies. The material contains 25.93 wt% of Pd(0) nanoparticles, with a diameter of 10-20 nm, well-dispersed on highly reduced graphene oxide containing a C/O ratio of 5.48. The efficacy of the CMG-PdNP system as a catalyst towards Heck cross-coupling with a variety of functionalized substrates has been demonstrated. Functionalization of reduced graphene oxide with heteroatoms like sulfur and nitrogen enhanced its dispersibility in organic solvents, and helped in stabilizing the active palladium species by acting as a ligand. The CMG-Pd composite exhibited an excellent catalytic activity with a substantially low catalytic loading (0.02 mol%), and the activity sustainable up to three reaction cycles. The remarkable effect might be a manifestation of N and S coordination to Pd, facilitating a high degree of dispersion and stabilization of Pd NPs onto the graphene surface.

Synthesis and tyrosinase inhibition activity of trans-stilbene derivatives

Synthesis of a focussed library of trans-stilbene compounds through Wittig and other base catalysed condensation reactions is presented. The synthesized stilbenes were screened for their inhibitory potential against murine tyrosinase activity to explore the structure activity relationship (SAR). Presence of electron withdrawing group (-CN) at the double bond and hydroxyl group or halogen atom especially at para-position on the aromatic rings was found to significantly elevate the inhibitory activity. Among all the compounds screened, compounds 2, 6, 8, 10, 11, 15 and 21 were found to exhibit appreciable inhibitory activity. Compound 21 ((E)-2,3-bis(4-Hydroxyphenyl)acryonitrile) was found to be the most active with an IC50 value of 5.06 μM which is less than half of the value 10.78 μM observed for resveratrol (common standard used in murine tyrosinase activity studies) under similar conditions. The results obtained from the present study reveal structural/functional group sensitivity for the tyrosinase inhibitory activity of stilbenoid moieties and are expected to be very helpful for the design and synthesis of novel, selective and effective tyrosinase inhibitors.

Palladium-catalyzed Mizoroki-Heck-type reactions of [Ph2SRfn][OTf] with alkenes at room temperature

The first Pd-catalyzed Mizoroki-Heck-type reaction of [Ph2SRfn][OTf] with alkenes is described. The reaction of [Ph2SRfn][OTf] (Rfn = CF3, CH2CF3) with alkenes in the presence of 10 mol% Pd[P(t-Bu)3]2 and TsOH at room temperature provided the corresponding phenylation products in good to high yields. The bases that benefit the traditional Mizoroki-Heck reactions severely inhibited the transformation with [Ph2SRfn][OTf], whereas acids significantly improved the reaction. This protocol supplies a new class of cross-coupling partners for Mizoroki-Heck-type reactions and gains important insights into the reactivity of phenylsulfonium salts either with or without fluorine-containing alkyl groups as the promising phenylation reagents in organic synthesis.

TRPA1 channels as targets for resveratrol and related stilbenoids

A series of twenty resveratrol analogues was synthesized and tested on TRPA1 and TRPV1 channels. None was able to significantly modulate TRPV1 channels. Conversely, most of them exhibited remarkably higher TRPA1 modulating activity than resveratrol. Optimal potency was observed with ortho monoxygenated stilbenes 6 and 17.

Synthesis and bioactivity of resveratrol analogues

It has been reported that resveratrol enhanced SIRT1 expression and significantly mimicked calorie restriction by stimulating Sir2 which is the most homologic homologue of SIRT1 of mammalian. A series of novel resveratrol derivatives were designed and synthesized as novel SIRT1 activator candidates. These synthesized compounds were characterized by spectral (1H NMR) analysis and examined for their Sir2 activation against yeast parental strain-BY4743 at a concentration of 100 μM/L by Bioscreen C MBR machine. Several compounds showed a promising Sir2 activation activity compared with resveratrol. Meanwhile, the structure-activity relationships with Sirt2 activation activities were also discussed.

Transition-metal-free semihydrogenation of diarylalkynes: Highly stereoselective synthesis of trans -alkenes using Na2S·9H 2O

A highly stereoselective and efficient transition-metal-free semihydrogenation of internal alkynes to E-alkenes using cheap and green water as hydrogen donor is described. The reactions are conducted under convenient conditions and provide products in good to excellent yields, with broad substrate scope, including a variety of diarylalkynes.