7466-60-6

Usage

Uses

Used in Organic Synthesis:
(2E)-1-(4-iodophenyl)-3-phenylprop-2-en-1-one is utilized as a reagent in organic synthesis for the preparation of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, contributing to the synthesis of complex organic molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (2E)-1-(4-iodophenyl)-3-phenylprop-2-en-1-one is used as a key intermediate in the development of new drugs. Its chemical properties make it a valuable component in the creation of novel therapeutic agents.
Used in Medicinal Chemistry:
(2E)-1-(4-iodophenyl)-3-phenylprop-2-en-1-one is employed as a subject of study in medicinal chemistry due to its potential antimicrobial and anti-inflammatory properties. These characteristics position the compound as a candidate for further research and development into treatments for various diseases and conditions.
Used in Antimicrobial Applications:
(2E)-1-(4-iodophenyl)-3-phenylprop-2-en-1-one is used as an antimicrobial agent, leveraging its ability to combat microorganisms. This application is crucial in the development of new antibiotics and antimicrobial therapies.
Used in Anti-inflammatory Applications:
(2E)-1-(4-iodophenyl)-3-phenylprop-2-en-1-one is also used for its anti-inflammatory properties, making it a potential agent in the treatment of inflammation-related disorders. Its role in this area could lead to advancements in managing chronic inflammatory conditions.

Upstream product

• 68120-56-9 1-(4-iodophenyl)ethanol 
• 100-51-6 benzyl alcohol 
• 140-10-3 (E)-3-phenylacrylic acid 
• 79477-88-6 2-(4-iodophenyl)-2-oxoacetic acid 
• 13329-40-3 4-Iodoacetophenone 
• 100-52-7 benzaldehyde 

Downstream Products

• 1094374-71-6 1-(4-iodophenyl)-3-phenylpropan-1-one 
• 1256705-50-6 1-(4-iodophenyl)-4-nitro-3-phenylbutan-1-one 
• 1256705-52-8 C₃₂H₂₁I₂N₃ 
• 1256705-56-2 C₃₂H₂₀BF₂I₂N₃ 
• 1401797-58-7 (E)-1-(4-iodophenyl)-3-phenyl-N-(benzenesulfonyl)prop-2-en-1-imine 

Relevant academic research and scientific papers

Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation

The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.

Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes

Formal [5 + 1] cycloadditions between aryl-substituted vinylcyclopropanes and nitrenoid precursors are reported. The method, which employs Rh2(esp)2 as a catalyst, leads to the highly regioselective formation of substituted tetrahydropyridines. Preliminary mechanistic studies support a stepwise, polar mechanism enabled by the previously observed Lewis acidity of Rh-nitrenoids. Overall, this work expands the application of nitrene-transfer cycloaddition, a relatively underexplored approach to heterocycle synthesis, to the formation of six-membered rings.

Synthesis of α, β - unsaturated ketone method

A synthetic method for [alpha],[beta]-unsaturated ketone is a method which catalyzes a primary alconol and a secondary alcohol to oxidize and couple by a supported catalyst. The method includes the steps of adding the primary alconol, the secondary alcohol, an alkali and the catalyst into the mixed solvent mixing water and tert-butyl alcohol; stirring at 0-100 DEG C for 0.5-36 hours under the existence of an oxidizing agent. The yield of [alpha],[beta]-unsaturated ketone can reach 99% in the oxidation coupling reaction system. The synthetic method is environment friendly and has high atom economy and reaction efficiency. Moreover, the synthetic method uses non-noble metal catalyst, so that the production cost is greatly reduced.

Iron-facilitated oxidative radical decarboxylative cross-coupling between α-oxocarboxylic acids and acrylic acids: An approach to α,β-unsaturated carbonyls

The first Fe-facilitated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution has been developed. This transformation is characterized by its wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents, thus providing an efficient and expeditious approach to an important class of α,β-unsaturated carbonyls frequently found in bioactive compounds. The synthetic potential of the coupled products is also demonstrated in subsequent functionalization reactions. Preliminary mechanism studies suggest that a free radical pathway is involved in this process: the generation of an acyl radical from α-oxocarboxylic acid via the excision of carbon dioxide followed by the addition of an acyl radical to the α-position of the double bond in acrylic acid then delivers the α,β-unsaturated carbonyl adduct through the extrusion of another carbon dioxide.

Ruthenium-catalyzed conjugate hydrogenation of ?±,?2-enones by in situ generated dihydrogen from paraformaldehyde and water

Notwithstanding that the highly selective hydrogenation of ?±,?2-enones to allylic alcohols can be realized by using Noyori's Ru bifunctional system, the selective reduction of the C=C bonds in ?±,?2-enones without touching the C=O bonds still lacks a general, simple, and efficient procedure. Ruthenium-catalyzed conjugate hydrogenation of various ?±,?2-enones to saturated ketones with high selectivity was investigated. The most important feature of this procedure was that hydrogen in situ generated from paraformaldehyde (or formalin) and water was employed as the reductant.

Efficient Protocol for the Synthesis of Novel Spiro[acenaphthylene-1,2′-pyrrolidin]-2-one Compounds

An efficient catalyst-free synthesis of 3′-benzoyl-4′,5′-diphenyl-2H-spiro[acenaphthylene-1,2′-pyrrolidin]-2-one derivatives via one-pot 1,3-dipolar cycloaddition of acenaphthenequinone, arylmethyl amines, and chalcones with high regioselectivity is described. The structure of the cycloadducts were characterized by infrared, high-resolution mass spectrometry (electrospray ionization), 1H NMR, and 13C NMR spectra, and the structure of 4a was confirmed using x-ray single-crystal structure analysis.

Solvent-free synthesis, spectral correlations and antimicrobial activities of some aryl e 2-propen-1-ones

Totally 38 aryl E 2-propen-1-ones including nine substituted styryl 4-iodophenyl ketones have been synthesised using solvent-free SiO 2-H3PO4 catalyzed Aldol condensation between respective methyl ketones and substituted benzaldehydes under microwave irradiation. The yields of the ketones are more than 80%. The synthesised chalcones were characterized by their analytical, physical and spectroscopic data. The spectral frequencies of synthesised substituted styryl 4-iodophenyl ketones have been correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. The antimicrobial activities of 4-iodophenyl chalcones have been studied using Bauer-Kirby method.

COMPOSITION FOR TREATING DIABETES AND METABOLIC DISEASES AND A PREPARATION METHOD THEREOF

Disclosed is a chalcone composition for treating diabetes and metabolic syndromes. In particular, the chalcone compound bound with 2-halogen in ring A significantly decreases the blood glucose level in the in vitro anti-diabetic effect experiment. In the in vivo animal model, the leading chalcone compound can prevent the progression of diabetes and control the blood glucose level, and there is no significant difference in the gains in body weight. Throughout the seven-week administration, there are no hepatic or renal toxicity observed.

2-(3-oxo-1,3-diphenylpropyl)malonic acids as potent allosteric ligands of the PIF pocket of phosphoinositide-dependent kinase-1: Development and prodrug concept

The protein kinase C-related kinase 2 (PRK2)-interacting fragment (PIF) pocket of phosphoinositide-dependent kinase-1 (PDK1) was proposed as a novel target site for allosteric modulators. In the present work, we describe the design, synthesis, and structure-activity relationship of a series of 2-(3-oxo-1,3-diphenylpropyl)malonic acids as potent allosteric activators binding to the PIF pocket. Some congeners displayed AC50 values for PDK1 activation in the submicromolar range. The potency of the best compounds to stabilize PDK1 in a thermal stability shift assay was in the same order of magnitude as that of the PIF pocket binding peptide PIFtide, suggesting comparable binding affinities to the PIF pocket. The crystal structure of PDK1 in complex with compound 4h revealed that additional ionic interactions are mainly responsible for the increased potency compared to the monocarboxylate analogues. Notably, several compounds displayed high selectivity for PDK1. Employing a prodrug strategy, we were able to corroborate the novel mechanism of action in cells.

Synthesis of chalcone derivatives as potential anti-diabetic agents

Chalcones bearing electron donating or electron withdrawing substitutions were prepared and their glucose uptake activity was evaluated. Chalcone derivatives were synthesized in one step protocol with high purity and yield. Chalcones with chloro, bromo, iodo and hydroxy substitutions at position 2 on A-ring exhibited the highest activity with glucose medium concentration (210 to 236 mg/dl) compared to pioglitazone and rosiglitazone (230 and 263 mg/dl, respectively). Also chalcones with iodo substitution at position 3 on A-ring were comparably active (≤ 238 mg/dl). The structure-activity relationship of the tested chalcones was studied and the findings were supported statistically.