28587-05-5

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(4-chlorophenyl)-3-(dimethylamino)-2-propen-1-one is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique chemical structure allows it to be a key component in the development of new medications, contributing to the advancement of pharmaceutical research and drug discovery.
Used in Organic Compound Synthesis:
In the field of organic chemistry, 1-(4-chlorophenyl)-3-(dimethylamino)-2-propen-1-one is utilized as an intermediate for the synthesis of a range of organic compounds. Its versatile structure enables it to be a valuable building block in the creation of diverse chemical products.
Used as a Reagent in Chemical Reactions:
1-(4-chlorophenyl)-3-(dimethylamino)-2-propen-1-one serves as a reagent in various chemical reactions, facilitating the transformation of other compounds and contributing to the overall progress of chemical research and development.
Used in Dye and Pigment Synthesis:
As a precursor for the synthesis of dyes and pigments, 1-(4-chlorophenyl)-3-(dimethylamino)-2-propen-1-one plays a significant role in the colorants industry. Its involvement in the production process helps create a wide array of dyes and pigments used in various applications, such as textiles, plastics, and printing inks.

InChI:InChI=1/C11H12ClNO/c1-13(2)8-7-11(14)9-3-5-10(12)6-4-9/h3-8H,1-2H3

Upstream product

• 99-91-2 para-chloroacetophenone 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 20353-93-9 Gold's reagent 
• 68-12-2 N,N-dimethyl-formamide 
• 15724-88-6 trans-1-(4-chlorophenyl)-3-chloroprop-2-en-1-one 
• 124-40-3 dimethyl amine 
• 68760-10-1 1-(4-Chlor-phenyl)-3-hydroxy-prop-2-en-1-on 
• 139943-10-5 N,N-dimethyl-1,3-butadien-1-amine 
• 74780-48-6 1--3-oxidopyridinium 
• 5815-08-7 tert-Butoxybis(dimethylamino)methane 
• 74793-93-4 1--3-hydroxypyrimidinium chloride 
• 18503-89-4 N,N-dimethylformamide diisopropyl acetal 

Downstream Products

• 102291-55-4 2-Amino-6-(4-chlorphenyl)-3-nitropyridin 
• 112778-86-6 4-(4-Chloro-phenyl)-benzo[4,5]imidazo[1,2-a]pyrimidine 
• 112778-87-7 2-(4-Chloro-phenyl)-benzo[4,5]imidazo[1,2-a]pyrimidine 
• 7064-32-6 5-(4-chlorophenyl)-1,2-oxazole 
• 7089-20-5 [3-chloro-3-(4-chloro-phenyl)-allylidene]-dimethyl-ammonium; perchlorate 
• 36175-15-2 1-(6-(4-chlorophenyl)-2-methylpyridin-3-yl)ethan-1-one 
• 1134193-17-1 4-(o-chlorophenyl)-1-(p-bromophenyl)-3-(p-chlorobenzoyl)-1,4-dihydropyridine 
• 1134193-26-2 1-(o-chlorophenyl)-2-(o-methylphenyl)-5-(p-chlorobenzoyl)-1,2-dihydropyridine 
• 1134193-03-5 4-phenyl-1-phenyl-3-(p-chlorobenzoyl)-1,4-dihydropyridine 
• 1134193-07-9 4-phenyl-1-(p-fluorophenyl)-3-(p-chlorobenzoyl)-1,4-dihydropyridine 
• 4640-66-8 p-chlorobenzoylacetonitrile 
• 59843-58-2 5(3)-(4-chlorophenyl)-1H-pyrazole 
• 14063-77-5 (Z)-3-chloro-3-(4-chlorophenyl)acrylaldehyde 
• 244625-23-8 (Z)-β-bromo-β-(4-chlorophenyl)acrolein 

Relevant academic research and scientific papers

Access to α,α-dihaloacetophenones through anodic C[dbnd]C bond cleavage in enaminones

We have developed a method to synthesize α,α-dihaloketones under electrochemical conditions. In this reaction, the Cl- or Br- is oxidized to Cl2 or Br2 at the anode, which undergoes two-step addition reactions with the N,N-dimethyl enaminone, and finally breaks C[dbnd]C of the N,N-dimethyl enaminone to generate α,α-dihaloketones. The electrosynthesis reaction can be conveniently carried out in an undivided electrolytic cell at room temperature. In addition, various functional groups are compatible with this green protocol which can be applied simultaneously to the gram scale without significantly lower yield.

DDQ-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene

An efficient 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene is developed. It provides a variety of α-alkenylated 1,3-dicarbonyl compounds in moderate to good yields under mild conditions.

Synthesis, characterization, and antimicrobial activity investigations of ruthenium (II)–bipyridine complexes of ciprofloxacin derivatives

A series of ruthenium (II) complexes derived from the reaction between cis-bis (2,2′-bipyridine) dichloro ruthenium (II) dihydrate and enaminone derivatives of ciprofloxacin were synthesized and fully characterized using elemental analysis, cyclic voltammetry and different spectroscopic techniques (Uv–vis, FTIR, NMR, mass spectroscopy, and X-ray photoelectron spectrometry (XPS)). The isolated compounds were tested for their antibacterial and antifungal activities against gram-negative and gram-positive bacteria. The FTIR data revealed that ciprofloxacin derivatives act as bidentate ligands through the pyridone carbonyl and the carboxylate oxygen atom. The UV–visible data showed that the charge transfer CT band is blue shifted upon the coordination of the ciprofloxacin derivatives compared to the CT band of the parent complex. The XPS results revealed the characteristic peaks of Ru3p3/2 and Ru3p1/2 as well as Ru3d5/2 and Ru3d3/2, which confirmed the assembly of the ruthenium (II) ciprofloxacin derivative complexes. Cyclic voltammetry data showed that the ciprofloxacin enaminone derivatives have a similar reduction potential for the Ru (II)/Ru (III) redox couple, and it revealed that the coordination of the ruthenium (II) ion altered the redox property of the ligands and enhanced their electron transfer rate. The electrochemical and the UV–visible results suggest that the ciprofloxacin derivative ligands are (Formula presented.) -acceptor ligands. Further, the complexes showed higher antibacterial activities than the parent ciprofloxacin antibiotic and did not show antifungal activities among the tested fungi strains.

A new approach for the synthesis of novel naphthoquinone chalcone hybrid compounds

A facile and efficient synthesis of novel naphthoquinone-based chalcone hybrids (7 and 24) via the microwave-assisted one-pot three-component reactions of 2-substituted-1,4-naphthoquinones, N,N-dimethylformamide dimethyl acetal (DMF-DMA), and acetophenone derivatives has been reported. Whereas the synthesis of hybrids 7 proceeded via a condensation, 1,4-addition, rotation, elimination, and [1,3]-H shift sequence of steps, the synthesis of hybrids 24 were formed through a three-step sequence including condensation, 1,4-addition, and elimination reactions.

Efficient synthesis, structure elucidation, and anti-parasitic activities of novel quinolinyl β–enaminones

In the present study, a novel series of side chain-modified quinoline β-enaminones were synthesized in good-to-excellent yields. The structures of all the synthesized compounds have been established with the help of spectral and analytical data and also b

An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes asC4units

An efficient method has been described to synthesize dicarbonyl functionalized 1,3-dienes by cleaving the CC bond of enaminones with cyclopropenes in the presence of a rhodium catalyst. The acetate-substituted cyclopropenes are judiciously chosen as standardC4units of 1,3-diene precursors. The reactions are believed to undergo a unique cutting and insertion process, involving a CC bond cleavage of the enaminone and insertion of a newC(sp2) source with the formation of two C-C single bonds. A broad range of substrates can be used to synthesize the corresponding 1,3-dienes under very mild reaction conditions, including low catalyst-loading, ambient temperature, and a neutral reaction solvent.

Synthesis of a new series of pyrazolo[1,5-a]pyrimidines as CDK2 inhibitors and anti-leukemia

Based on the structural study of previously known CDK2 inhibitors, a new series of pyrazolo[1,5-a]pyrimidine derivatives was designed and synthesized. The target compounds were biologically assessed as potent CDK2 inhibitors and promising anti-leukemia hi

One-Pot Synthesis of Symmetrical and Asymmetrical 3-Amino Diynes via Cu(I)-Catalyzed Reaction of Enaminones with Terminal Alkynes

An economical and efficient protocol for the direct construction of amino skipped diynes through the Cu(I)-catalyzed reaction of enaminones and terminal alkynes has been described. Different kinds of symmetrical and asymmetrical 3-amino diynes could be ob

Stereoselective synthesis of trifluoromethyl-substituted 2: H -furan-amines from enaminones

A straightforward strategy for synthesis of highly functionalized trifluoromethyl 2H-furans is described. The copper catalyzed method relies on a cascade cyclic reaction between enaminones and N-tosylhydrazones. This method allows the synthesis of 2-amino

Synthesis and biological evaluation of (3/4-(pyrimidin-2-ylamino)benzoyl)-based hydrazine-1-carboxamide/carbothioamide derivatives as novel RXRα antagonists

Abnormal alterations in the expression and biological function of retinoid X receptor alpha (RXRα) have a key role in the development of cancer. Potential modulators of RXRα as anticancer agents are explored in growing numbers of studies. A series of (4/3-(pyrimidin-2-ylamino)benzoyl)hydrazine-1-carboxamide/carbothioamide derivatives are synthesised and evaluated for anticancer activity as RXRα antagonists in this study. Among all synthesised compounds, 6A shows strong antagonist activity (half maximal effective concentration (EC50) = 1.68 ± 0.22 μM), potent anti-proliferative activity against human cancer cell lines HepG2 and A549 cells (50% inhibition of cell viability (IC50) values 50 values > 100 μM). Further bioassays indicate that 6A inhibits 9-cis-RA-induced activity in a dose-dependent manner, and selectively binds to RXRα-=LΒD with submicromolar affinity (Kd = 1.20 × 10?7 M). 6A induces time-and dose-dependent cleavage of poly ADP-ribose polymerase, and significantly stimulates caspase-3 activity, leading to RXRα-dependent apoptosis. Finally, molecular docking studies predict the binding modes for RXRα-LBD and 6A.