42762-56-1

Upstream product

• 26562-24-3 3-bromo-2-methoxypropene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 21040-45-9 Cinnamyl acetate 
• 97674-02-7 tributyl(1-ethoxyvinyl)stannane 
• 54985-34-1 trans-1-phenyl-1-penten-3-ol 
• 100-52-7 benzaldehyde 
• 78-94-4 methyl vinyl ketone 
• 55815-92-4 2-Methyl-2-((E)-3-phenyl-allyl)-[1,3]dioxolane 
• 21663-35-4 1-phenyl-pent-3-ene-1,2-diol 
• 1608-27-1 ((1E)-penta-1,3-dien-1-yl)benzene 
• 1896-62-4 (E)-benzalacetone 
• 98204-74-1 2-(Hydroxy-phenyl-methyl)-1-methyl-cyclopropanol 
• 41108-92-3 3,3-diacetyl-1-phenyl-1-propylene 
• 122-78-1 phenylacetaldehyde 

Downstream Products

• 64976-68-7 (E)-1-acetyl-1-(β-styryl)-cyclopentane 
• 64976-67-6 (E)-3,3-diethyl-5-phenylpent-4-en-2-one 

Relevant academic research and scientific papers

Fischer chromium carbene complexes as nucleophiles in palladium-catalyzed allylic substitution reactions

The Pd-catalyzed reaction of carbanions derived from chromium aminocarbene complexes with allylic acetates and carbonates smoothly affords the corresponding allyl-substituted aminocarbenes. On the contrary, the same reaction of the anion derived from pentacarbonyl[(methoxy)methylcarbene]chromium(0) with cinnamyl acetate affords 5-methoxy-1-phenylhexa-1,5-diene, the product of 1-methoxyethen-1-yl group transfer.

Efficient Dimerization Disruption of Leishmania infantum Trypanothione Reductase by Triazole-phenyl-thiazoles

Inhibition of Leishmania infantum trypanothione disulfide reductase (LiTryR) by disruption of its homodimeric interface has proved to be an alternative and unexploited strategy in the search for novel antileishmanial agents. Proof of concept was first obtained by peptides and peptidomimetics. Building on previously reported dimerization disruptors containing an imidazole-phenyl-thiazole scaffold, we now report a new 1,2,3-triazole-based chemotype that yields noncompetitive, slow-binding inhibitors of LiTryR. Several compounds bearing (poly)aromatic substituents dramatically improve the ability to disrupt LiTryR dimerization relative to reference imidazoles. Molecular modeling studies identified an almost unexplored hydrophobic region at the interfacial domain as the putative binding site for these compounds. A subsequent structure-based design led to a symmetrical triazole analogue that displayed even more potent inhibitory activity over LiTryR and enhanced leishmanicidal activity. Remarkably, several of these novel triazole-bearing compounds were able to kill both extracellular and intracellular parasites in cell cultures.

Synthesis of Allylboranes via Cu(I)-Catalyzed B-H Insertion of Vinyldiazoacetates into Phosphine-Borane Adducts

Cu(I) catalysts enable C-B bond formation via direct insertion of vinyldiazoacetates into B-H bonds of borane-phosphine Lewis adducts to form phosphine-protected allylboranes under mild conditions. The resulting allylborane-phosphine Lewis adducts can be used in the diastereoselective allylation of aldehydes directly without the need for removal of the phosphine. The allylation reaction proceeds with high diastereoselectivity and yields 5,6-disubstituted dihydropyranones after treatment with an appropriate acid.

TRIAZOLE-PHENYL-THIAZOLE HETEROCYCLES AS INNOVATIVE INHIBITORS OF TRYPANOTHIONE REDUCTASE AND THEIR USE AS LEISHMANICIDES

The present invention refers to new compounds useful in the treatment of leishmaniasis and, more particularly, to a series of 5-6-5 triazole-phenyl-thiazole heterocycles capable of inhibiting both activity and dimerization of L. infantum TryR in enzymatic assays at low micromolar concentrations and endowed with potent in vitro activity against promastigote and amastigote forms of Leishmania which indicates a good permeability across the plasma membrane of the parasites.

Catalyst- and Substituent-Controlled Switching of Chemoselectivity for the Enantioselective Synthesis of Fully Substituted Cyclobutane Derivatives via 2 + 2 Annulation of Vinylogous Ketone Enolates and Nitroalkene

The first regioselective, diastereoselective, and enantioselective organocatalyzed Michael-Michael cascade of vinylogous ketone enolates and nitroalkenes for the construction of fully substituted cyclobutanes is achieved by the deployment of the appropriate chiral squaramide catalyst and the pertinent substituent on the substrate. The domino reaction provided cyclobutanes with four contiguous stereocenters, including a quaternary center in good yields with diastereomeric ratio of >20:1 and with enantioselectivities of mostly up to 98% enantiomeric excess (ee). The structures and the absolute configurations of the adducts were confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.

Controlling the α/γ-Reactivity of Vinylogous Ketone Enolates in Organocatalytic Enantioselective Michael Reactions

The first regio-, diastereo-, and enantioselective direct Michael reaction of β,γ-unsaturated ketones with nitroolefins is enabled by Br?nsted base/hydrogen-bonding bifunctional catalysis. A squaramide-substituted tertiary amine catalyzes the reaction of a broad range of β,γ-unsaturated ketones to proceed at the α-site exclusively, giving rise to adducts with two consecutive tertiary carbon stereocenters in diastereomeric ratios of up to >20:1 and enantioselectivities generally in the 90–98 % ee range.

Selective functionalization of a variety of hydrocarbon c(sp3)-h bonds initiated by Cp?W(NO)(CH2CMe3)(η3-CH2CHCHPh)

Cp?W(NO)(CH2CMe3)(η3-CH2CHCHPh) (1) effects C(sp3)-H activations of methane, ethane, propane, and n-butane exclusively at their terminal carbons and forms the corresponding Cp?W(NO)(alkyl)(η3-CH2- CHCHPh) complexes. It also activates (n-Bu)2O, 1-chloropropane, and Me4Si in a similar manner. Exposure of the Cp?W(NO)(alkyl)(η3-CH2CHCHPh) complexes to carbon monoxide results in initial 1,1-CO insertion into the newly formed tungsten-alkyl bonds and formation of the corresponding η1-acyl complexes, some of which can be isolated. Additional functionalization of the C-H activation products occurs upon exposure to CO under more forcing conditions. Such treatment produces η2-bound unsaturated-ketone complexes resulting from CO insertion into the W-alkyl σ bonds followed by cross-coupling of the η1-acyl and the η3-allyl ligands and coordination of CO at the resulting vacant coordination site at tungsten. The unsaturated ketones can be released from the metal's coordination spheres either by photolysis of the complexes in MeCN or by further exposure of them to CO. All new compounds have been characterized by conventional spectroscopic and analytical methods, and the solid-state molecular structures of six of them have been established by single-crystal X-ray crystallographic analyses.

Anti-Markovnikov Oxidation of β-Alkyl Styrenes with H2O as the Terminal Oxidant

Oxygenation of alkenes is one of the most straightforward routes for the construction of carbonyl compounds. Wacker oxidation provides a broadly useful strategy to convert the mineral oil into higher value-added carbonyl chemicals. However, the conventional Wacker chemistry remains problematic, such as the poor activity for internal alkenes, the lack of anti-Markovnikov regioselectivity, and the high cost and chemical waste resulted from noble metal catalysts and stoichiometric oxidant. Here, we describe an unprecedented dehydrogenative oxygenation of β-alkyl styrenes and their derivatives with water under external-oxidant-free conditions by utilizing the synergistic effect of photocatalysis and proton-reduction catalysis that can address these challenges. This dual catalytic system possesses the single anti-Markovnikov selectivity due to the property of the visible-light-induced alkene radical cation intermediate.

Ruthenium(IV) porphyrin catalyzed highly selective oxidation of internal alkenes into ketones with Cl2pyNO as terminal oxidant

A new method for the conversion of internal alkenes into ketones without cleavage of CC bond by using dichlororuthenium(IV) meso-tetrakis(2,6- dichlorophenyl)porphyrin [RuIV(TDCPP)Cl2] as catalyst and 2,6-dichloropyridine N-oxide(Cl2pyNO) as oxidant is developed.

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.