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Usage

General Description

2,4-Pentadien-1-one, 5-(4-methoxyphenyl)-1-phenyl- is a chemical compound with a molecular formula C16H14O2. It is a yellowish liquid with a strong odor, commonly used in the manufacturing of perfumes and flavorings. 2,4-Pentadien-1-one, 5-(4-methoxyphenyl)-1-phenyl- is also known for its potential pharmaceutical applications, as it exhibits anti-inflammatory and antioxidant properties. Additionally, it has been used in the synthesis of various biologically active compounds, making it an important intermediate in organic chemistry. However, it should be handled with caution and protective measures, as it can be harmful if ingested, inhaled, or if it comes into contact with the skin or eyes.

Upstream product

• 1963-36-6 4-methoxycinnamaldehyde 
• 98-86-2 acetophenone 
• 853400-97-2 [2-(4-methoxyphenyl)cyclopropyl]acetaldehyde 
• 76711-42-7 (E)-2-(4-methoxyphenyl)-1-trimethylsilylethene 
• 65420-47-5 (E)-1-phenyl-3-(trimethylsilyl)prop-2-en-1-one 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 3185-60-2 1-(4-Methoxy-phenyl)-5-phenyl-pentadien-(1,3)-ol-⁽⁵⁾ 
• 1438403-18-9 (3R,4E)-5-(4-methoxyphenyl)-3-methyl-1-phenylpent-4-en-1-one 
• 1235563-71-9 (R,E)-5-(4-methoxyphenyl)-3-(nitromethyl)-1-phenylpent-4-en-1-one 
• 1239278-99-9 (S,E)-2-[5-(4-methoxyphenyl)-1-oxo-1-phenylpent-4-en-3-yl]malononitrile 

Relevant academic research and scientific papers

Palladium-Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation

A new strategy for the generation of the active Pd-alkyl species from aminal via C—N bond activation has been established, in which the formation of zwitterionic intermediate through aza-Michael addition of aminal to nitrodienes or dienones is identified as a key step for the activation of the C—N bond. The efficient strategy has enabled a new palladium-catalyzed α-aminomethylation of nitrodienes and dienones via double C—N bond activation. The scope and versatility of the reaction were demonstrated and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to furnish the desired α-aminomethylated products in moderate to good yields with excellent regioselectivities and E/Z selectivities.

In silico studies, nitric oxide, and cholinesterases inhibition activities of pyrazole and pyrazoline analogs of diarylpentanoids

A new series of pyrazole, phenylpyrazole, and pyrazoline analogs of diarylpentanoids (excluding compounds 3a, 4a, 5a, and 5b) was pan-assay interference compounds-filtered and synthesized via the reaction of diarylpentanoids with hydrazine monohydrate and phenylhydrazine. Each analog was evaluated for its anti-inflammatory ability via the suppression of nitric oxide (NO) on IFN-γ/LPS-activated RAW264.7 macrophage cells. The compounds were also investigated for their inhibitory capability toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), using a modification of Ellman's spectrophotometric method. The most potent NO inhibitor was found to be phenylpyrazole analog 4c, followed by 4e, when compared with curcumin. In contrast, pyrazole 3a and pyrazoline 5a were found to be the most selective and effective BChE inhibitors over AChE. The data collected from the single-crystal X-ray diffraction analysis of compound 5a were then applied in a docking simulation to determine the potential binding interactions that were responsible for the anti-BChE activity. The results obtained signify the potential of these pyrazole and pyrazoline scaffolds to be developed as therapeutic agents against inflammatory conditions and Alzheimer's disease.

Anti-corrosive property of bioinspired environmental benign imidazole and isoxazoline heterocyclics: A cumulative studies of experimental and DFT methods

In the present study, four imidazoline (IDZ) and four isoxazolines (ISO) heterocyclics differing in the nature of methoxy (-OCH3) and aromatic (phenyl and naphthyl) moieties are synthesized, characterized and evaluated as corrosion inhibitors for mild steel in acidic solution of 1 M HCl. Results showed that imidazoline based heterocyclic compounds are better corrosion inhibitors than isoxazoline based heterocyclics and both classes of compounds showed inhibition efficiency of more than 85% at 20 mgL?1 concentration. Results further showed that inhibitors containing methoxy, phenyl, and naphthyl moieties showed higher protection efficiency as compared to the inhibitors without these moieties. PDP Study revealed that investigated IDZs and ISOs acted as mixed type inhibitors and their adsorption on the metallic surface followed the Langmuir adsorption isotherm model. All the experimental results were corroborated by density function theory (DFT) based quantum chemical calculations. Numerous DFT based indices calculated for neutral as well as protonated forms of the IDZs and ISOs in order to get better insight about metal-IDZs/ISOs interactions. Outcomes of the DFT analysis showed that protonated (cationic) form of the all the inhibitors are more strongly adsorbed on the metallic surface as compared to their neutral form.

Visible-Light Induced Direct Synthesis of Polysubstituted Furans from Cyclopropyl Ketones

In this article, a photoredox protocol for the synthesis of furans via oxidative coupling of olefin generated in situ from cyclopropyl ketones with ketonic oxygen atom is presented. Moreover, bromination of furans in the presence of overstoichiometric oxidant has been achieved with high regioselectivity.

Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxide inhibitors

A series of forty-five 1,5-diphenylpenta-2,4-dien-1-one analogues were synthesized and evaluated for their nitric oxide (NO) inhibition activity in IFN-γ/LPS-activated RAW 264.7 cells. Compounds 3h, 7a, 7d and 7e exhibited comparable or significantly higher activity than the standard, curcumin (IC50 = 14.69 ± 0.24 μM). Compound 7d, a 5-methylthiophenyl-bearing analogue, displayed the most promising NO-inhibitory activity with an IC50 value of 10.24 ± 0.62 μM. The 2D and 3D QSAR analyses performed revealed that a para-hydroxyl group on ring B and an α,β-unsaturated ketone moiety on the linker are crucial for a remarkable anti-inflammatory activity. Based on ADMET and TOPKAT analyses, compounds 3h, 7a and 7d are predicted to be nonmutagenic and to exhibit high blood-brain barrier (BBB) penetration, which indicates that they are potentially effective drug candidates for treating central nervous system (CNS) related disorders.

Oxidative cross-coupling of vinylsilanes in water

Palladium-promoted cross-dimerization reaction of alkenylsilanes is reported for the first time, which is also one of the very first studies on oxidative cross-coupling between vinylic organometallic reagents. The reaction occurs at room temperature in aqueous micelles and represents a convenient access to all-trans push-pull butadienes.

Copper-catalyzed asymmetric 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ-unsaturated ketones

A highly regioselective and enantioselective copper-catalyzed 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ- unsaturated ketones was developed. The 1,4-addition products were obtained regioselectively in high yields with up to 98% ee. The Royal Society of Chemistry 2013.

NHC-catalyzed annulation of enals to 2,4-dien-1-ones: Efficient diastereoselective synthesis of 1,3-diaryl-4-styrenyl cyclopentenes

Nucleophilic heterocyclic carbene (NHC)-catalyzed annulation strategy has been utilized for the efficient synthesis of styrenyl-substituted cyclopentenes from 2,4-dienones. Georg Thieme Verlag Stuttgart New York.

Tandem mass spectrometry based investigation of cinnamylideneacetophenone derivatives: Valuable tool for the differentiation of positional isomers

Cinnamylideneacetophenones have been extensively used as versatile starting materials in numerous different transformations. The structural characterization of this type of compounds is, therefore, of crucial importance since it can give information on th

Asymmetric direct michael addition of acetophenone to α,β- unsaturated aldehydes

The asymmetric direct Michael addition of ,-unsaturated aldehydes with acetophenone catalyzed by a Jorgensen-Hayashi-catalyst in methanol was developed and the corresponding Michael products of -keto aldehydes could be afforded in up to 82% yield and 98% ee. Georg Thieme Verlag Stuttgart.