145799-89-9

Usage

Uses

Used in Organic Synthesis:
(2E)-3-(Dimethylamino)-1-(1-naphthyl)prop-2-en-1-one is utilized as a key intermediate in organic synthesis, contributing to the formation of complex organic molecules. Its unique structure allows it to participate in a range of chemical reactions, facilitating the creation of diverse chemical entities.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2E)-3-(Dimethylamino)-1-(1-naphthyl)prop-2-en-1-one is used as a reagent in chemical reactions for the development of new drugs. Its potential biological activities and pharmacological properties make it a valuable component in medicinal chemistry and drug discovery research.
Used in Agrochemicals:
(2E)-3-(Dimethylamino)-1-(1-naphthyl)prop-2-en-1-one also finds application in the agrochemical sector, where it serves as a reagent in the synthesis of various agrochemical products. Its structural features and reactivity are harnessed to create compounds that can be used in agricultural applications.
Used in Materials Science:
In the field of materials science, (2E)-3-(Dimethylamino)-1-(1-naphthyl)prop-2-en-1-one is employed for its potential to contribute to the development of new materials with specific properties. Its chemical structure allows it to be integrated into the design and synthesis of advanced materials for various applications.

Upstream product

• 941-98-0 1'-naphthacetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 1419184-34-1 C₃₁H₂₇NO 
• 1419184-33-0 C₂₂H₁₄F₃NO 
• 1192655-37-0 3-acetyl-4-(naphthalene-1-carbonyl)-1-phenyl-1H-pyrazole 
• 1273553-96-0 3-benzoyl-4-(naphthalene-1-carbonyl)-1-phenyl-1H-pyrazole 
• 1273553-97-1 4-(naphthalene-1-carbonyl)-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester 
• 1273553-98-2 4-(naphthalene-1-carbonyl)-1-phenyl-3-(thienyl-2-carbonyl)-1H-pyrazole 
• 524036-27-9 4-naphthalen-1-yl-2-phenyl-2,6-dihydropyrazolo[3,4-d]pyridazin-7-one 
• 1273553-87-9 4-naphthalen-1-yl-2,7-diphenyl-2H-pyrazolo[3,4-d]pyridazine 
• 1273554-06-5 2-(4-chlorophenyl)-6-(naphthalene-1-carbonyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid ethyl ester 
• 1273553-95-9 2-(4-chlorophenyl)-3-imino-6-(naphthalene-1-carbonyl)-2,3-dihydropyridazine-4-carboxylic acid ethyl ester 
• 1273553-94-8 2-(4-chlorophenyl)-3-imino-6-(naphthalene-1-carbonyl)-2,3-dihydropyridazine-4-carbonitrile 
• 1273553-91-5 (4-chlorophenyl)(3-naphthalen-1-yl-1H-pyrazol-4-yl)diazene 
• 1273554-03-2 5-naphthalen-1-yl-2-thioxo-6-p-tolylazo-2,3-dihydro-1H-pyrido[2,3-d]pyrimidin-4-one 
• 1273554-02-1 5-naphthalen-1-yl-6-phenylazo-2-thioxo-2,3-dihydro-1H-pyrido[2,3-d]pyrimidin-4-one 

Relevant academic research and scientific papers

Discovery of highly potent tubulin polymerization inhibitors: Design, synthesis, and structure-activity relationships of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines

By removing 5-methyl and 6-acetyl groups in our previously reported compound 3, we designed a series of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine derivatives as potential tubulin polymerization inhibitors. Among them, compound 5e displayed low nanomolar antiproliferative efficacy on HeLa cells which was 166-fold higher than the lead analogue 3. Interestingly, 5e displayed significant selectivity in inhibiting cancer cells over HEK-293 (normal human embryonic kidney cells). In addition, 5e dose-dependently arrested HeLa in G2/M phase through the alterations of the expression levels of p-cdc2 and cyclin B1, and caused HeLa cells apoptosis by regulation of expressions of cleaved PARP. Further evidence demonstrated that 5e effectively inhibited tubulin polymerization and was 3-fold more powerful than positive control CA-4. Moreover, molecular docking analysis indicated that 5e overlapped well with CA-4 in the colchicine-binding site. These studies demonstrated that 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine skeleton might be used as the leading unit to develop novel tubulin polymerization inhibitors as potential anticancer agents.

Metal-free TBAI-catalyzed oxidative Csp3–S bond formation through Csp2–Csp2 bond and S–N bond cleavage: A new route to β-keto-Sulfones

A novel TBAI-catalyzed radical sulfonylation of readily available N,N-dimethylenaminones with sulfonylhydrazides to afford functionalized β-keto-sulfones has been developed. Various functional groups were tolerated well under the present oxidative conditions and the corresponding β-keto-sulfone compounds were obtained in moderate to good yields. Importantly, this transformation offered the first protocol for Csp3–S bond formation by oxidative Csp2–Csp2 bond cleavage in one step.

Enaminones as Synthons for a Directed C?H Functionalization: RhIII-Catalyzed Synthesis of Naphthalenes

The use of enaminones as effective synthons for a directed C?H functionalization is reported. Proof-of-concept protocols have been developed for the RhIII-catalyzed synthesis of naphthalenes, based on the coupling of enaminones with either alkynes or α-diazo-β-ketoesters. Two inherently reactive functionalities (hydroxy and aldehyde groups) are integrated into the newly formed cyclic framework and a broad range of substituents are tolerated, rendering target products readily available for further elaboration.

Olefin polymerization behavior of titanium(IV) pyridine-2-phenolate-6- (σ-aryl) catalysts: Impact of py-adjacent and phenolate substituents

A series of Ti(IV) post-metallocene bis(benzyl) precatalysts supported by tridentate pyridine-2-phenolate-6-(σ-aryl) [O,N,C] ligands, featuring various substituents on the σ-aryl (directly adjacent to the pyridine ring: fluoro, trifluoromethyl, benzo [C4H4]) and phenolate groups (tert-butyl, trifluoromethyl, cumyl, 1,1-diphenylethyl), have been prepared. Multinuclear (including 1H, 13C, and 19F) NMR characterizations of the complexes have been performed. The principal purpose of this study was to investigate the impact of these substituents upon ethylene polymerization reactivity and polymer properties. The cumyl-phenolate σ-naphthyl Ti precatalyst, in conjunction with [Ph 3C][B(C6F5)4], displays good activity and produces polyethylene with exceptionally high MW (Mn = 4 × 106) and an Mw/Mn value (2.5) approaching single-site character at 50 C, but multisite behavior is apparent for other catalysts. DFT calculations have been performed to probe the polymerization behavior and the role of the py-adjacent substituent. These studies revealed the possibility of two distinct polymerization reactions, namely conventional and ethylene-assimilated (comprising initial ethylene insertion into the Ti-C(σ-aryl) bond) chain propagation, and found that the latter is kinetically preferred. Furthermore, the viability of another kinetically competitive pathway, namely the isomerization of the ethylene-assimilated [Ti-CH2CH2-aryl] species via β-H elimination and 2,1-reinsertion, was also indicated.

L-proline-catalyzed activation of methyl ketones or active methylene compounds and DMF-DMA for syntheses of (2E)-3-dimethylamino-2- propen-1-ones

A cascade organocatalysis is reported for the nucleophilic and electrophilic dual activation taking place in the reaction of methyl ketones or active methylene compounds with DMF-DMA (N,N-dimethylformamide dimethyl acetal). L-Proline serves as an efficient organocatalyst in the covalent and noncovalent synchronous mode for the ambiphilic activation of various aryl, heteroaryl, and styryl methyl ketones, cyclic ketones, and 1,3-diketones with DMF-DMA to achieve the convenient syntheses of the versatile synthons (2E)-1-aryl/ heteroaryl/styryl-3-(dimethylamino)-2-propen-1-ones, (E)-α- [(dimethylamino)formylidene]cycloalkanones, and (E)-2-(dimethylamino) formylidene-1,3-diketones in high yields under solvent-free conditions.

Chemistry of the enaminone of 1-acetylnaphthalene under microwave irradiation using chitosan as a green catalyst

Enaminone 1 was reacted with hydrazonoyl halides 2a-d to yield 3,4-disubstituted pyrazoles 6a-d. Coupling with arenediazonium chlorides afforded the 2-(arylhydrazono)-3-(1-naphthalenyl)-3-oxopropionaldehydes 13a-c. Compounds 13 could be utilized for the s

Efficient organocatalytic dual activation strategy for preparing the versatile synthons (2 E)-1-(Het)aryl/styryl-3-(dimethylamino)prop-2-en-1-ones and -(E)-[(dimethylamino)methylene]cycloalkanones

A novel organocatalytic dual activation strategy is reported for an efficient synthesis of the versatile synthons (2E)-1-aryl/heteroaryl/styryl-3- (dimethylamino)prop-2-en-1-ones and -(E)-[(dimethylamino)methylene] cycloalkanones. 2-Guanidinoacetic acid (10 mol%) serves as an ambifunctional organocatalyst for the reaction of various aryl/heteroaryl/styryl methyl ketones and cyclic ketones having an -methylene moiety with N,N-dimethylformamide dimethyl acetal at 100 C for 1-3 hours under solvent-free conditions to afford the corresponding (2E)-3-(dimethylamino)prop-2-en-1-ones in 72-95% yields. Georg Thieme Verlag Stuttgart - New York.

A highly efficient regioselective one-pot synthesis of 2,3,6-trisubstituted pyridines and 2,7,7-trisubstituted tetrahydroquinolin-5-ones using K5CoW12O40·3H2O as a heterogeneous recyclable catalyst

A systematic investigation into the regioselective one-pot, three-component condensation of enaminones 1a-g, β-dicarbonyl compounds 2a-c, and ammonium acetate in the presence of a catalytic amount of K5CoW12O40·3H2O (0.01 equiv or 1.0 mol %) under solvent free conditions, as well as in refluxing isopropanol, has been reported. The reaction was highly efficient to produce 2,3,6-trisubstituted pyridines 3a-g, 4a-g, and novel 2,7,7-trisubstituted-5,6,7,8-tetrahydroquinoline-5-ones 5a-g in excellent yields. The present procedure offers advantages of short reaction time, simple work-up, and the catalyst exhibited remarkable reusable activity.

Synthesis of a novel series of 6,6′-disubstituted 4,4′-bipyrimidines by radical anion coupling: New π-accepting ligands for coordination chemistry

A new family of 6,6′-disubstituted 4,4′-bipyrimidine ligands has been prepared and characterized. The reduction potentials of the new ligands, as determined by cyclic voltammetry, indicate that these new ligands are considerably better π-acceptors than the ubiquitous 2,2′-bipyridine ligand, and are even superior to the parent unsubstituted 4,4′- bipyrimidine ligand. The substituents in 6,6′ positions of the 4,4′-bipyrimidine also cause a red-shift in the π→π* and n→π* absorptions throughout the UV region. The X-ray crystal structure of one member of the family of bipyrimidines demonstrates that the aryl substituents may lie coplanar with the pyrimidine rings in the solid state. The additional electron delocalization afforded by the aryl substituents on the pyrimidine rings contribute to the better π-accepting ability of these compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Microwave assisted synthesis of 1-aryl-3-dimethylaminoprop-2-enones: A simple and rapid access to 3(5)-arylpyrazoles

Condensation of aromatic acyl compounds with N,N-dimethylformamide diethyl acetal in a pressure tube under microwave heating gives 1-aryl-3-dimethylaminoprop-2-enones in almost quantitative yields. In the presence of hydrazine, these intermediates are transferred to the corresponding 3-arylpyrazoles.