19672-63-0

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one is used as a key intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique structure and functional groups allow for the creation of new compounds with potential therapeutic properties.
Used in Fine Chemicals Production:
In the fine chemicals sector, 1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one serves as an essential intermediate. Its versatile reactivity enables the development of specialty chemicals that can be utilized in a wide range of applications, from fragrances to dyes and other high-value products.
Used in Organic Chemistry Research:
1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one is also employed in organic chemistry research as a model compound for studying various reaction mechanisms and exploring new synthetic pathways. Its unique structure provides researchers with valuable insights into the behavior of α,β-unsaturated ketones and their potential applications in chemical synthesis.

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 99-91-2 para-chloroacetophenone 
• 101272-32-6 2,3-dibromo-1-(4-chloro-phenyl)-3-p-tolyl-propan-1-one 
• 123-54-6 acetylacetone 
• 109-77-3 malononitrile 
• 37620-37-4 (E)-4-chloro-4'-methylchalcone 
• 19672-63-0 (2E)-1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one 
• 104-88-1 4-chlorobenzaldehyde 
• 122-00-9 para-methylacetophenone 
• 166823-95-6 (E)-3-(4-chlorophenyl)-1-(p-tolyl)prop-2-en-1-ol 
• 166824-02-8 (E)-1-(4-chlorophenyl)-3-(p-tolyl)prop-2-en-1-ol 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 7099-88-9 4-chlorophenylglyoxylic acid 

Downstream Products

• 128883-48-7 6-(4-chlorophenyl)-2-oxo-6-(4-tolyl)-2,3,4,5-tetrahydro-3-pyridinecarboxamide 
• 132577-28-7 1-acetyl-3-(4-chlorophenyl)-5-(4-methylphenyl)-2-pyrazoline 
• 97691-62-8 6-(4-Chloro-phenyl)-4-p-tolyl-1H-pyrimidin-2-one 
• 127394-76-7 6-(4-Chloro-phenyl)-2-methoxy-4-p-tolyl-nicotinonitrile 
• 127394-67-6 6-(4-Chloro-phenyl)-2-ethoxy-4-p-tolyl-nicotinonitrile 
• 101272-32-6 2,3-dibromo-1-(4-chloro-phenyl)-3-p-tolyl-propan-1-one 
• 622-47-9 4-tolylacetic acid 
• 74-11-3 para-chlorobenzoic acid 
• 110220-77-4 p-tolyl-3-(4-chlorophenyl)oxiran-2-yl-methanone 
• 1132907-14-2 (4-chlorophenyl)(2-(4-chlorophenyl)-2-hydroxy-4,5-di-p-tolylcyclopentyl)methanone 
• 1027736-78-2 1-(4-chlorophenyl)-3-(1H-indol-3-yl)-3-(4-methylphenyl)propan-1-one 
• 1217356-40-5 7-(4-chlorophenyl)-1,3-dimethyl-5-p-tolylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione 
• 1198089-02-9 C₃₅H₃₀ClFN₂ 
• 1260620-87-8 6-(4-chlorophenyl)-3-methyl-1-phenyl-4-p-tolyl-1H-pyrazolo[3,4-b]pyridine 

Relevant academic research and scientific papers

Design and synthesis of quinoline-pyrimidine inspired hybrids as potential plasmodial inhibitors

Presently, artemisinin-based combination therapy (ACT) is the first-line therapy of Plasmodium falciparum malaria. With the emergence of malaria parasites that are resistant to ACT, alternative antimalarial therapies are urgently needed. In line with this

Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides

The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the 4,7-positions showed high activity in the photodimerization via an energy transfer pathway.

Bu4NHSO4-Catalyzed Direct N-Allylation of Pyrazole and its Derivatives with Allylic Alcohols in Water: A Metal-Free, Recyclable and Sustainable System

Allylic amines are valuable and functional building blocks. Direct N-allylation of pyrazole and its derivatives as an atom economic strategy to provide allylic amines has been achieved only using commercial Bu4NHSO4 as the metal-free catalyst and water as the solvent without any additives. 11–93% isolated yields were obtained for the N-allylation of pyrazole and its derivatives with allylic alcohols. Bu4NHSO4 could be reused for six times by simple extraction nearly without loss of catalytic activity and was also suitable for a gram-scale production. The reaction of allylic ether and pyrazole did not occur to give the desired product indicated that allylic ether was not the active intermediate in the pathway. Density functional theory (DFT) calculations reveal that there are hydrogen bonding effects among substrates, solvent and catalyst, especially the one formed between allylic alcohol and H2O. Control experiments in different protic solvents further demonstrate the intermolecular hydrogen bonding of allylic alcohol and water. (Figure presented.).

N-Heterocyclic Carbene Catalyzed Synthesis of Trisubstituted Epoxides via Tandem Amidation/Epoxidation Sequence

A tandem amidation/epoxidation sequence between various substituted chalcones and N,N-dimethylformamide (DMF) for the synthesis of trisubstituted epoxides employing N-heterocyclic carbene catalysis was developed. This reaction was performed under metal-free conditions in the presence of tert-butyl hydroperoxide (TBHP) as the oxidant. Trisubstituted epoxides bearing a ketone and an amide functionality (N,N-dimethyl formyl group) were synthesized starting from a wide range of chalcones in moderate to good yields with excellent diastereoselectivity.

Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia-derived cells: Role of PKCβ

In this study, a series of 20 chalcone derivatives was synthesized, and their antiproliferative activity was tested against the human T cell acute lymphoblastic leukemia-derived cell line, CCRF-CEM. On the basis of the structural features of the most active compounds, a new library of chalcone derivatives, according to the structure–activity relationship design, was synthesized, and their antiproliferative activity was tested against the same cancer cell line. Furthermore, four of these derivatives (compounds 3, 4, 8, 28), based on lower IC50 values (between 6.1 and 8.9 μM), were selected for further investigation regarding the modulation of the protein expression of RACK1 (receptor for activated C kinase), protein kinase C (PKC)α and PKCβ, and their action on the cell cycle level. The cell cycle analysis indicated a block in the G0/G1 phase for all four compounds, with a statistically significant decrease in the percentage of cells in the S phase, with no indication of apoptosis (sub-G0/G1 phase). Compounds 4 and 8 showed a statistically significant reduction in the expression of PKCα and an increase in PKCβ, which together with the demonstration of an antiproliferative role of PKCβ, as assessed by treating cells with a selective PKCβ activator, indicated that the observed antiproliferative effect is likely to be mediated through PKCβ induction.

Aryl-4,5-dihydro-1H-pyrazole-1-carboxamide derivatives bearing a sulfonamide moiety show single-digit nanomolar-to-subnanomolar inhibition constants against the tumor-associated human carbonic anhydrases IX and XII

A series of new 3-phenyl-5-aryl-N-(4-sulfamoylphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide derivatives was designed here, synthesized, and studied for carbonic anhydrase (CAs, EC 4.2.1.1) inhibitory activity against the human (h) isozymes I, II, and VII (cytosolic, off-target isoforms), and IX and XII (anticancer drug targets). Generally, CA I was not effectively inhibited, whereas effective inhibitors were identified against both CAs II (KIs in the range of 5.2-233 nM) and VII (KIs in the range of 2.3-350 nM). Nonetheless, CAs IX and XII were the most susceptible isoforms to this class of inhibitors. In particular, compounds bearing an unsubstituted phenyl ring at the pyrazoline 3 position showed 1.3-1.5 nM KIs against CA IX. In contrast, a subset of derivatives having a 4-halo-phenyl at the same position of the aromatic scaffold even reached subnanomolar KIs against CA XII (0.62-0.99 nM). Docking studies with CA IX and XII were used to shed light on the derivative binding mode driving the preferential inhibition of the tumor-associated CAs. The identified potent and selective CA IX/XII inhibitors are of interest as leads for the development of new anticancer strategies.

Donor-acceptor fluorophores as efficient energy transfer photocatalysts for [2 + 2] photodimerization

Mild [2 + 2] photodimerization of enone substrates was induced by donor-acceptor fluorophores. Enone substrates were activated efficiently for anti-head to head dimerizations with a high yield (up to 83%) and high selectivity. The adjustable excited state potential also allows donor-acceptor fluorophores to be used for isomerization of the above substrates, confirming the potential of donor-acceptor fluorophores as energy transfer photocatalysts.

Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts

A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading.

Accessing dihydro-1,2-oxazine via cloke-wilson-type annulation of cyclopropyl carbonyls: application toward the diastereoselective synthesis of pyrrolo[1,2- b][1,2]oxazine

A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.

Alkylation of Indoles with α,β-Unsaturated Ketones using Alumina in Hexanes

We evaluated the influence of solvent on the alumina-promoted C3-alkylation of indoles with α,β-unsaturated ketones. We found that lipophilic solvents were generally superior to hydrophilic ones with hexanes offering the 3-alkyl indole products in high yields. Thus, we demonstrate an inexpensive and procedurally simple new process that pairs acidic alumina with hexanes to achieve this important Michael alkylation. The substrate scope includes twenty-four examples with reaction yields ranging from 61 to 96%. (Figure presented.).