31083-73-5

Upstream product

• 1443-80-7 4-cyanophenyl methyl ketone 
• 100-52-7 benzaldehyde 
• 536-74-3 phenylacetylene 
• 105-07-7 4-cyanobenzaldehyde 
• 93628-96-7 (2E)-3-phenyl-1-(4-cyanophenyl)prop-2-en-1-one 
• 100-42-5 styrene 
• 19710-56-6 hydroxycarbene 
• 126747-14-6 4-cyanophenylboronic acid 

Downstream Products

• 88405-29-2 4-[1-(4-Nitro-phenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-benzonitrile 
• 88405-28-1 4-[1-(4-Amino-phenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-benzonitrile 
• 259674-54-9 4-(1-hydroxy-3-phenylallyl)benzonitrile 
• 93628-96-7 (2E)-3-phenyl-1-(4-cyanophenyl)prop-2-en-1-one 
• 1180009-49-7 4-(1-acetyl-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)benzonitrile 
• 143429-16-7 1-(4-cyanophenyl)-3-hydroxy-3-phenyl-1-propanone 

Relevant academic research and scientific papers

Fluorescent Molecular Logic Gates Driven by Temperature and by Protons in Solution and on Solid

Temperature-driven fluorescent NOT logic is demonstrated by exploiting predissociation in a 1,3,5-trisubstituted Δ2-pyrazoline on its own and when grafted onto silica microparticles. Related Δ2-pyrazolines become proton-driven YES an

Iron-Catalyzed Chemoselective Reduction of α,β-Unsaturated Ketones

An iron-catalyzed chemo- and diastereoselective reduction of α,β-unsaturated ketones into the corresponding saturated ketones in mild reaction conditions is reported herein. DFT calculations and experimental work underline that transfer hydride reduction is a more facile process than hydrogenation, unveiling the fundamental role of the base.

Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin

Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose-response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues.

Cascade Reaction by Chemo- and Biocatalytic Approaches to Obtain Chiral Hydroxy Ketones and anti 1,3-Diols

A chemo- and biocatalytic cascade approach was applied for the stereoselective synthesis of hydroxy ketones and the corresponding 1,3-diols. A new class of tridentate N,N,O ligands was used with copper(II) complexes for the asymmetric β-borylation of α,β-unsaturated compounds. The complex containing ligand L5 emerged as the best performer, and it gave the organoborane derivatives with good ee values. The corresponding keto–alcohol compounds were then bioreduced by yeasts. The biotransformation set up with Rhodotorula rubra allowed (R)-keto–alcohols and (S,S)-diols to be obtained with up to 99 % ee and up to 99 % de in favor of the anti enantiomers.

Transition-Metal-Free Catalytic Formal Hydroacylation of Terminal Alkynes

Although hydroacylation is a very useful reaction for producing ketones from aldehydes with 100% atom efficiency, classical Rh-catalyzed hydroacylation presents several problems, including the need for transition metal catalysts, unwanted decarbonylation of aldehydes, and difficulty in regioselectivity control. However, formal hydroacylation utilizing the nucleophilicity of terminal alkynes can avoid these problems. In this work, we have achieved transition-metal-free formal hydroacylation of terminal alkynes using an Mg3Al-CO3-layered double hydroxide as a heterogeneous catalyst. This system was applicable to the efficient synthesis of α,β-unsaturated ketones with various substituents, and the catalyst can be reused without a significant loss of catalytic performance.

Borylation and selective reduction of α,β-unsaturated ketones under mild conditions catalyzed by Cu nanoparticles

An effective strategy for synthesis of Cu nanoparticles is designed, these nanoparticles have high catalytic activity in conjugate addition of B2(pin)2and α,β-unsaturated ketones. The reaction of protodeboration can proceed with adding NaOtBu. In this way, a new method to reduce the conjugated alkenes of α,β-unsaturated ketones is developed with organoboranes as intermediates. Cu nanocrystals also have excellent performance in gram-scale reaction and recycling experiment. A possible mechanism is proposed.

Synthesis, anti-inflammatory and antioxidant activity of ring-a-monosubstituted chalcone derivatives

A library of ring-A-monosubstituted chalcone derivatives (4a-4i, 5a and 5b) was designed and synthesised. The structures as well as the identities of these compounds were established on the basis of spectral (1H NMR, 13C NMR, FT-IR and Mass) and elemental (C, H, N) analyses. All the derivatives were evaluated for their anti-inflammatory and antioxidant activities in vitro using the inhibition of protein denaturation and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays, respectively. The results indicated a promising anti-inflammatory activity for most of the synthesised compounds with many derivatives showing activities similar to or greater than that of the standard. The sulphonamide-substituted chalcones 4h, 4i, 5a and 5b were found to be the most active derivatives across the concentration range tested. However, all the derivatives exhibited rather mild antioxidant activity compared to the ascorbic acid standard. Interestingly, it was observed that the unsubstituted parent chalcone was one of the optimal compounds with only the trifluoromethyl analogue 4a showing better activity as an antioxidant. The two regioisomeric aminochalcones and 4′-cyanochalcone 4b also seemed to possess decent antioxidant potential.

Lithium amidoborane, a highly chemoselective reagent for the reduction of α,β-unsaturated ketones to allylic alcohols

Lithium amidoborane (LiNH2BH3, LiAB for short), is capable of chemoselectively reducing α,β-unsaturated ketones to the corresponding allylic alcohols at ambient temperature. A mechanistic study shows that the reduction is via a double hydrogen transfer process. The protic H(N) and hydridic H(B) in amidoborane add to the O and C sites of the carbonyl group, respectively.

Palladium-catalyzed oxidative carbonylative coupling reactions of arylboronic acids with styrenes to chalcones under mild aerobic conditions

Do the coupling: A palladium-catalyzed oxidative carbonylative coupling process of arylboronic acid with styrenes to chalcone has been developed. The reactions proceed under mild conditions using air as the terminal oxidant reagent.

Reactions in Strongly Basic Media. Part 10. Base-catylysed Isomerisation of Z- to E-substituted Chalcones

The rate coefficients for the methoxide-catalysed isomerisation of substituted (Z)-chalcones have been measured in methanolic dimethyl sulfoxide (DMSO) at 30.0 deg C, as well as for (Z)-chalcone at several temperatures.The reactions are first order in substrate and base.Further, log k1 for the reaction of (Z)-chalcone and (Z)-4-nitrochalcone correlate with an acidity function, Ha, having slopes equal to 0.53 and 0.45, respectively.The effect of substitution has been assessed using the Hammett equation, with ρ equal to 1.99 for the β-phenyl group and 1.93 for the benzoyl group.For the (Z)-chalcone, the enthalpy and entropy of acti vation are 14.2 kcal mol-1 and -14 cal mol-1 K-1, respectively, and the kinetic solvent isotope effect, k2MeOD/k2MeOH, is ca. 2.0.The rate coefficients for the amine-catalysed isomerisation of (Z)-chalcone and (Z)-4-nitrochalcone in DMSO have been measured at 30.0 deg C.The amino bases are a series of secondary aliphatic amines and the Bronstedt coefficients, β, are given as 0.39 and 0.38, respectively.The isomerisation is considered to proceed by rate-determining attack of the base at the β-carbon of the (Z)-chalcone to form a carbanion.The "cis"-conformer of the carbanion then rotates to form the "trans"-conformer, which eliminates the base to give the (E)-chalcone.