3815-30-3

Upstream product

• 76781-64-1 6t-(4-methoxy-phenyl)-2,4-dioxo-hex-5-enoic acid ethyl ester 
• 4643-20-3 (E)-4-chloro-3-buten-2-one 
• 100-66-3 methoxybenzene 
• 129083-68-7 4-Hydroxy-4-(4-methoxy-phenyl)-1-(triphenyl-λ⁵-phosphanylidene)-butan-2-one 
• 108-22-5 Isopropenyl acetate 
• 123-11-5 4-methoxy-benzaldehyde 
• 541-50-4 2-acetoacetic acid 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 696-62-8 para-iodoanisole 
• 78-94-4 methyl vinyl ketone 
• 2091-46-5 triphenyl(prop-2-ynyl)phosphonium bromide 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 66107-29-7 4-methoxyphenyl triflate 

Downstream Products

• 101878-88-0 isonicotinic acid-[3t-(4-methoxy-phenyl)-1-methyl-allylidenehydrazide] 
• 38080-86-3 4-hydroxy-3-(1-(4-methoxyphenyl)-3-oxobutyl)-2H-chromen-2-one 
• 102474-07-7 4-hydroxy-3-[1-(4-methoxy-phenyl)-3-oxo-butyl]-7-methyl-coumarin 
• 109250-54-6 4-(4-hydroxy-3-methyl-phenyl)-4-(4-methoxy-phenyl)-butan-2-one 
• 109252-49-5 4-(2-hydroxy-3-methyl-phenyl)-4-(4-methoxy-phenyl)-butan-2-one 
• 26175-41-7 4-(4-methoxy-phenethyl)-thiazol-2-ylamine 
• 622-70-8 1-(4-methoxy-phenyl)-7-phenyl-hepta-1,4,6-trien-3-one 
• 76781-64-1 6t-(4-methoxy-phenyl)-2,4-dioxo-hex-5-enoic acid ethyl ester 
• 6597-43-9 1-(4-dimethylamino-phenyl)-5-(4-methoxy-phenyl)-penta-1,4-dien-3-one 
• 1102-06-3 4t-(4-methoxy-phenyl)-but-3-en-2-one-(2,4-dinitro-phenylhydrazone) 
• 75698-43-0 ethyl 6-(p-methoxyphenyl)-2,4-dioxocyclohexane-1-carboxylate 
• 66601-57-8 1,7-bis-(4-methoxy-phenyl)-hepta-1,4,6-trien-3-one 

Relevant academic research and scientific papers

Isotope effects, dynamic matching, and solvent dynamics in a Wittig reaction. Betaines as bypassed intermediates

The mechanism of the Wittig reaction of anisaldehyde with a stabilized ylide was studied by a combination of 13C kinetic isotope effects, conventional calculations, and molecular dynamics calculations in a cluster of 53 THF molecules. The isoto

An efficient Pd@Pro-GO heterogeneous catalyst for the α, β-dehydrogenation of saturated aldehyde and ketones

An Efficient Pd@Pro-GO heterogeneous catalyst was developed that can promote the α, β-dehydrogenation of saturated aldehyde and ketones in the yield of 73% ? 92% at mild conditions without extra oxidants and additives. Pd@Pro-GO heterogeneous catalyst was synthesized via two steps: firstly, the Pro-GO was obtained by the esterification reaction between graphene oxide (GO) and N-(tert-Butoxycarbonyl)-L-proline (Boc-Pro-OH), followed by removing the protection group tert-Butoxycarbonyl (Boc), which endowed the proline-functionalized GO with both the lewis acid site (COOH) and the bronsted base site (NH), besides, the pyrrolidine of proline also can form imine with aldehydes to activate these substrates; Second, palladium was dispersed on the proline-functionalized GO (Pro-GO) to obtained heterogeneous catalyst Pd@Pro-GO. Mechanistic studies have shown that the Pd@Pro-GO-catalyzed α,β-dehydrogenation of saturated aldehyde and ketones was realized by an improved heterogeneously catalyzed Saegusa oxidation reaction. Based on the obove characteristics, the Pd@Pro-GO will be widely used in the transition metal catalytic field.

Silica Jar-with-Lid as Chemo-Enzymatic Nano-Compartment for Enantioselective Synthesis inside Living Cells

Nanodevices, harvesting the power of synthetic catalysts and enzymes to perform enantioselective synthesis inside cell, have never been reported. Here, we synthesized round bottom jar-like silica nanostructures (SiJARs) with a chemo-responsive metal-silic

Design, green synthesis, antioxidant activity screening, and evaluation of protective effect on cerebral ischemia reperfusion injury of novel monoenone monocarbonyl curcumin analogs

Antioxidants with high efficacy and low toxicity have the potential to treat cerebral ischemia reperfusion injury (CIRI). Dienone monocarbonyl curcumin analogs (DMCA) capable of overcoming the instability and pharmacokinetic defects of curcumin possess notable antioxidant activity but are found to be significantly toxic. In this study, a novel skeleton of the monoenone monocarbonyl curcumin analogue sAc possessing reduced toxicity and improved stability was designed on the basis of the DMCA skeleton. Moreover, 32 sAc analogs were obtained by applying a green, simple, and economical synthetic method. Multiple sAc analogs with an antioxidant protective effect in PC12 cells were screened using an H2O2-induced oxidative stress damage model, and quantitative evaluation of structure–activity relationship (QSAR) model with regression coefficient of R2 = 0.918921 was built through random forest algorithm (RF). Among these compounds, the optimally active compound sAc15 elicited a potent protective effect on cell growth of PC12 cells by effectively eliminating ROS generation in response to oxidative stress injury by activating the Nrf2/HO-1 antioxidant signaling pathway. In addition, sAc15 exhibited good protection against CIRI in the mice middle cerebral artery occlusion (MCAO) model. In this paper, we provide a novel class of antioxidants and a potential compound for stroke treatment.

Aminium cation-radical catalysed selective hydration of (E)-aryl enynes

The hydration of carbon-carbon triple bonds is an important and atom economic synthetic transformation. Herein, we report a mild and selective method for the catalytic Markovnikov hydration of (E)-aryl enynes to the corresponding enones, mediated through the bench-stable aminium salt, tris(4-bromophenyl)ammoniumyl hexachloroantimonate (TBPA). The chemoselective and diastereoselective method proceeds under neutral metal-free conditions, delivering excellent product yields from terminal and internal alkyne units. The synthesis of biologically important (E)-3-styrylisocoumarins, including a formal synthesis of the natural product achlisocoumarin III, demonstrates the utility of this novel transformation.

Olefin Metathesis, p-Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces

p-Cresol as additive to the Grubbs second generation catalyst (GII) allows the cross-metathesis of acrylates with prop-1-en-1-ylbenzenes under conditions that only give the prop-1-en-1-ylbenzene self-metathesis product in the absence of cresol. NMR and IR spectroscopy, MALDI-TOF MS and XPS supported the formation of a ruthenium benzylidene with hydrogen bonds between p-cresol and the chloride ligands of GII. XPS furthermore confirmed p-cresol to increase the binding energies of the GII Ru 3d5/2, 3d3/2, 3p3/2 and 3p1/2 photoelectron lines, whereas 1H NMR spectroscopy indicated the carbene carbon and hydrogen to be shielded. It is thus postulated that p-cresol allows for more facile interaction between electron-deficient compounds and the ruthenium benzylidene by decreasing the electron density on the metal center and increasing the electron density on the carbene.

Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds

An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.

Pd-catalyzed oxidative Heck-type arylation of vinyl ketones, alkenes, and acrylates with Sb-aryl-tetrahydrodibenz[c,f][1,5]azastibocines

The Pd-catalyzed cross-coupling reactions of Sb-aryl-1,5-azastibocines with alkenes are described. The reactions of azastibocines with alkenes such as vinyl ketones, alkenes, and acrylates in the presence of 10 mol% PdCl2 at 80 °C in DMA under aerobic conditions produced Heck adducts in moderate-to-excellent yields. Single-crystal X-ray and NMR analysis revealed that the aryl donors in this reaction, the Sb-aryl-1,5-azastibocines, are hypervalent compounds that display N–Sb intramolecular non-bonding interaction. These are the first examples of Pd-catalyzed Heck-type arylations using heterocyclic hypervalent organoantimony compounds. Although the reactions proceeded efficiently with the azastibocines, they hardly progressed with trivalent and pentavalent triarylantimony reagents.

Catalytic Enantioselective Conjugate Addition of Stereodefined Di- and Trisubstituted Alkenylaluminum Compounds to Acyclic Enones

Catalytic enantioselective conjugate addition (ECA) reactions with readily accessible and stereochemically defined E-, Z-, di- and trisubstituted alkenyl aluminum compounds are disclosed. Transformations are promoted by various NHC-copper catalysts (NHC=N-heterocyclic carbene), which are derived from enantiomerically pure sulfonate imidazolinium salts. The desired products were obtained in up to 89% yield and >99:1 e.r.; the alkenyl moiety was transferred with complete retention of its stereochemical identity in all instances. The scope and limitations of the approach, key mechanistic attributes, and representative functionalization are presented as well. (Figure presented.).

One-pot two-step chemoenzymatic deracemization of allylic alcohols using laccases and alcohol dehydrogenases

A series of enantioenriched (hetero)aromatic secondary allylic alcohols has been synthesized through deracemization of the corresponding racemic mixtures combining a non-selective chemoenzymatic oxidation (laccase from Trametes versicolor and oxy-radical TEMPO) and a stereoselective biocatalyzed reduction (lyophilized cells of E. coli overexpressing an alcohol dehydrogenase, ADH). Both steps were performed in aqueous medium under very mild reaction conditions. After optimization, a sequential one-pot two-step protocol was set up, obtaining the corresponding chiral alcohols in moderate to high conversions (48–95%) and enantiomeric excess (65->99% ee). Depending on the ADH stereopreference, both antipodes from these valuable chiral synthons could be prepared, even at preparative scale (119?178 mg), in a straightforward manner.