2892-16-2

Usage

Preparation

Preparation by Fries rearrangement of 4-chlorophenyl propionate without solvent, with titanium tetrachloride at 50° for 3 h (59%) Preparation by acylation of p-chlorophenol with propionic acid in the presence of boron trifluoride in a sealed tube at 150° for 5 h (82%).

InChI:InChI=1/C9H9ClO2/c1-2-8(11)7-5-6(10)3-4-9(7)12/h3-5,12H,2H2,1H3

Upstream product

• 61469-49-6 4-chlorophenyl propionate 
• 106-48-9 4-chloro-phenol 
• 802294-64-0 propionic acid 

Downstream Products

• 610-99-1 1-(2-Hydroxy-phenyl)-propan-1-on 
• 99854-13-4 (4-chloro-2-propionyl-phenoxy)-acetic acid 
• 104416-45-7 1-(5-Chloro-2-hydroxy-phenyl)-3-hydroxy-2-methyl-propan-1-one 
• 91289-35-9 {C₆H₃(OH)(Cl)C(CH₂CH₃)}2NCH₂CH₂N 
• 1939-66-8 1-[5-Chloro-2-(2,3-dihydroxy-propoxy)-phenyl]-propan-1-one 
• 68597-44-4 5-chloro-2-methoxypropiophenone 
• 1373267-31-2 4-chloro-2-propionylphenyl trifluoromethanesulfonate 
• 2892-15-1 3-bromo-5-chloro-2-hydroxypropiophenone 

Relevant academic research and scientific papers

Synthesis, experimental and theoretical study of novel 2-haloalkyl (-CF2H, -CCl2H, -CF2CF3)-, 3-bromo and bromomethyl substituted chromones

A set of seven new chromones with 2-haloalkyl (-CF2H, -CCl2H, -CF2CF3) and 3-bromo and bromomethyl substituents were synthesized. The novel compounds were studied by DFT calculations and characterized by vibrational spectroscopy (IR and Raman) in solid state, and NMR (1H, 13C and 19F) and UV–vis spectroscopy in solution. The crystal structure of 3-dibromomethyl-2-difluoromethyl chromone was determined by X-ray diffraction. Due to extended π-bond delocalization, the organic framework is planar and lies on a crystallographic m-mirror plane. The intermolecular non-covalent interactions of 3-dibromomethyl-2-difluoromethyl chromone, as π?π stacking arrangements, F?H hydrogen bonds and O?Br contacts were evaluated by Hirshfeld surfaces analysis. These intermolecular contacts, which affect the absorption bands location of the involved groups, were also detected in the vibrational spectra.

5-Chlorobenzofuran-2-carboxamides: From allosteric CB1 modulators to potential apoptotic antitumor agents

Cannabinoids as THC and the CB1 allosteric modulator CBD were reported to have antiproliferative activities with no reports for other CB1 allosteric modulators as the 5-chloroindole-2-carboxamide derivatives and their furan congeners. Based on the antiproliferative activity of two 5-chlorobenzofuran-2-carboxamide allosteric CB1 modulators, a series of novel derivatives was designed and synthesized. The synthesized compounds were tested in a cell viability assay using human mammary gland epithelial cell line (MCF-10A) where all the compounds exhibited no cytotoxic effects and more than 85% cell viability at a concentration of 50 μM. Some derivatives showed good antiproliferative activities against tumor cells as compounds 8, 15, 21 and 22. The most active compound 15 showed equipotent activity to doxorubicin. Compounds 7, 9, 15, 16, 21 and 22 increased the level of active caspase 3 by 4–8 folds, compared to the control cells in MCF-7 cell line and doxorubicin as a reference drug. Compounds 15 and 21, the most activecaspase-3 inducers, increase the levels of caspase 8 and 9 indicating activation of both intrinsic and extrinsic pathways and showed potent induction of Bax, down-regulation of Bcl-2 protein levels and over-expression of Cytochrome C levels in MCF-7 cell lines. Compound 15 exhibited cell cycle arrest at the Pre-G1 and G2/M phases in the cell cycle analysis of MCF-7 cell line. The drug Likeness profile of the synthesized compounds showed that all the compounds were predicted to have high oral absorption complying with different pharmacokinetics filters.

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.

Regioselective synthesis of 3,5-diaryl-4-methylisoxazoles

A new class of isoxazole derivatives, namely 2-(3-aryl-4-methylisoxazol-5- yl)phenols, has been efficiently synthesized through the regioselective reaction of 2-aryl-3-methylchromones with hydroxylamine. The products were characterized by spectroscopic me

Flavanonol derivatives and hair-nourishing, hair growing compositions containing the derivatives

The present invention relates to flavanonol derivatives represented by formula (1): STR1 (wherein R1 represents an alkyl group, and each of R2 and R3 represents a hydrogen atom, an alkyl group which may have a substituent,

Synthesis and activity of 2-methyl-3-aminopropiophenones as centrally acting muscle relaxants

Some novel 2-methyl-3-aminopropiophenones were synthesized and their centrally acting muscle relaxant activities were,evaluated for an inhibitory effect on the flexor reflex in rats. The structure-activity relationships are discussed. In this series 2-methyl-3-pyrrolidino-1-(4-trifluoromethylphenyl)-propan-1-one (28) showed significant centrally acting muscle relaxant activity. In addition, the activities of each enantiomer (28-(S) and (R)) were studied along with their acute toxicities. Compound 28-(R) was found to exhibit more potent activity and weaker acute toxicity than 28-(S). Accordingly, compound 28-(R) (NK433) is under development as a novel centrally acting muscle relaxant.