50343-13-0

Usage

Type of compound

Ketone derivative

Functional groups

Hydroxyl group, chlorine atom, and two methyl groups

Structure

Phenyl ring with a hydroxyl group at the 6th position, a chlorine atom at the 3rd position, and two methyl groups at the 2nd and 4th positions

Applications

Organic synthesis, pharmaceutical research, building block for the synthesis of various pharmaceutical and biologically active compounds, potential applications in the development of agrochemicals and other specialty chemicals

Interactions with biological systems

Presence of hydroxyl and chlorine groups allows for potential interactions, making it an important target for medicinal chemistry research

Industrial applications

Potential due to its structural features

Upstream product

• 105508-87-0 6-chloro-4,5,7-trimethyl-coumarin 
• 855160-93-9 6-chloro-3,4,5,7-tetramethyl-coumarin 
• 408511-69-3 3-chloro-6-methoxy-2,4-dimethylacetophenone 
• 7446-70-0 aluminium trichloride 
• 22012-58-4 4-chloro-3, 5, dimethyl phenyl acetate 
• 14002-91-6 4,5,7-trimethylcoumarin 
• 88-04-0 4-Chloro-3,5-dimethylphenol 
• 64-19-7 acetic acid 
• 855161-81-8 6-amino-4,5,7-trimethyl-coumarin 
• 53666-70-9 3,4,5,7-tetramethyl-coumarin 
• 1021178-44-8 3-chloro-4-trimethylsilanyloxy-pent-3-en-2-one 
• 63446-76-4 1-methyl-1,3-bis(trimethylsilyloxy)buta-1,3-diene 
• 119138-87-3 6-chloro-2,5,7-trimethyl-4H-chromen-4-one 
• 855158-90-6 3,4,5,7-tetramethyl-6-nitro-coumarin 

Downstream Products

• 18980-12-6 2-Ethyl-3,5-dimethyl-p-Chlorophenol 
• 105508-79-0 1-(3-Chloro-6-methoxymethoxy-2,4-dimethyl-phenyl)-ethanone 
• 105508-84-7 3-(3-Chloro-6-methoxymethoxy-2,4-dimethyl-phenyl)-3-hydroxy-butyric acid tert-butyl ester 

Relevant academic research and scientific papers

New Mn(II), Co(II), Ni(II) and Cu(II) homoleptic complexes with 6-chloro-5-7-dimethyl-4oxo-4H-chromene-3-carbaldehydes and its heteroleptic complexes with quinoline-8 ol: synthesis, characterization and antimicrobial activity

In the present study, the synthesis of ligand 6-chloro-5-7-dimethyl-4oxo-4H-chromene-3-carbaldehydes by three steps from the substituted phenol. The formed product in the first step was further processed by fries rearrangement reaction and subsequently Vilsmeier–Haack reaction. Then, its homoleptic and heteroleptic complexes with Mn(II), Co(II), Ni(II) and Cu(II) metal ions by using second ligand quinolin-8-ol were synthesized. The ligand and complexes were characterized by different techniques, such as electron dispersive spectroscopy and elemental analysis (CHN), Fourier transform infrared (FTIR), electronic spectroscopy and magnetic susceptibility, 1H-Nuclear magnetic resonance spectroscopy and mass spectra of ligand, electron spin resonance (ESR), thermogravimetric analysis, powder X-ray diffraction, scanning electron microscopy (SEM) and molar conductivity. The spectroscopic analysis like NMR and the FTIR shows that the both ligands are bidentate in nature. The UV–visible spectra show the homoleptic complex of Cu(II) shows square planer, while M = Ni(II), Co(II) and Mn(II) shows octahedral in nature. While the complexes with heteroleptic ligands from square planer geometry with Cu(II) and Ni(II) while Co(II) and Mn(II) show octahedral geometries. The geometry was also supported by magnetic susceptibility and FTIR spectra. The ESR spectra of Cu(II) complexes shows both are square planer geometry and the G-value was more than 4 indicating the absence of exchange interaction between Cu(II) metal ions in the solid state. The powder X-ray diffraction was used to determine the crystal system of all the complexes, while supporting to this X-ray diffraction the SEM was also taken for the nanostructure of complexes was developed or not. Then, the solution state conductivity of the complexes shows electrolytic in nature. Further, these complexes were evaluated for its antimicrobial activity by agar well diffusion method and structure–activity relationship. The ligands show antimicrobial activity against S.typhi. The Ni(II) does not show antibacterial activity, while complexes Cu(II), Co(II) and Mn(II) shows good activity against the gram-positive and the gram-negative bacteria. The heteroleptic ligand complex (6) of Cu(II) shows higher antifungal activity as compared with Ni(II), Co(II) and Mn(II) complexes.

Bioactivity study of thiophene and pyrazole containing heterocycles

Chalcones 3a-f were prepared by reacting thiophene containing pyrazolyl aldehyde (2) with different 2-hydroxy acetophenones 1a-f. The compounds 3a-f were transformed into different Pyrazolines 4a-f. The formation of chromene derivatives 5a-f occurred from the cyclization of 3a-f, which were then transformed into pyrazole derivatives 6a-f. Newly synthesized compounds have promising antibacterial activity against S. typhii and S. aureus, while weak activity against B. subtilis and E. coli. Compounds 5d and 6d had significant antifungal action towards A. niger, while most of the compounds were moderately active towards T. viride. Some of the synthesized compounds showed promising α-amylase inhibitory activity at 1 mg/mL concentration.

Synthesis and Antibacterial Screening of Some New Pyrazolylchromones and Pyrazolylcoumaran-3-ones

Some new pyrazolylchromones 4a-e (flavone analogs) and pyrazolylcoumaran-3-ones 5a-e (aurone analogs) were synthesized by refluxing chalcones 3a-e in dimethyl sulfoxide/I2 and Pyridine/ Hg(OAc)2, respectively. Spectral techniques such as infrared, proton nuclear magnetic resonance, and mass spectrometry were used to confirm the structures of newly synthesized compounds. These compounds were studied for their antibacterial activities toward Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Salmonella typhi. Some of these compounds showed promising activity against test organisms.

Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel-Crafts acylation/Allan-Robinson reaction

A facile and efficient synthesis of chromen-4-one and isoflavone frameworks is achieved by the domino C-acylation/O-acylation/aldolization sequence. This operationally simple one-pot elegant strategy provides structurally unique chromen-4-ones and isoflavones directly from phenols via concomitant formation of multiple C-C and C-O bonds in a single operation. The outcomes of the buttressing effect, substituent dependence, and catalyst and solvent specificity during the course of the Friedel-Crafts acylation reactions are demonstrated and supported by fitting experiments.

SPIROKETONE ACETYL-COA CARBOXYLASE INHIBITORS

The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating mammals suffering from the condition of being overweight.

Regioselective synthesis of 4-chlorophenols, 10-chloro-7-hydroxy-6H-benzo[c]chromen-6-ones, and 4-chloro-1-hydroxy-9H-fluoren-9-ones based on [3+3] cyclizations of 1,3-bis(silyloxy)-1,3-dienes with 2-chloro-3-silyloxy-2-en-1-ones

A variety of 4-chlorophenols, 10-chloro-7-hydroxy-6H-benzo[c]chromen-6-ones, and 4-chloro-1-hydroxy-9H-fluoren-9-ones were prepared by formal [3+3] cyclizations of 1,3-bis(silyloxy)-1,3-dienes with 2-chloro-3-(silyloxy)alk-2-en-1-ones.

Synthesis of functionalized 4-chlorophenols and 1,4-dihydroquinones by [3+3] cyclization of 1,3-bis-silyl enol ethers with 2-chloro- and 2-acyloxy-3-(silyloxy)alk-2-en-1-ones

Functionalized 4-chlorophenols and 1,4-dihydroquinones were prepared by [3+3] cyclization of 1,3-bis-silyl enol ethers with 2-chloro- and 2-acyloxy-3-(silyloxy)alk-2-en-1-ones.