67405-31-6

Usage

Molecular structure

complex with a tetrahydro-4H-pyran-4-one core, attached with two 4-chlorophenyl groups and two methyl groups

Source

mostly produced synthetically, not commonly found in nature

Applications

used in pharmaceutical industry for designing new drug molecules with potential antitumor and anti-inflammatory activities

Potential applications

in organic synthesis and material science due to unique molecular properties

Upstream product

• 85336-33-0 t-2,t-6-di-p-chlorophenyl-c-3, c-5-dimethyl-r-4-aminooxane 
• 104-88-1 4-chlorobenzaldehyde 
• 96-22-0 pentan-3-one 

Relevant academic research and scientific papers

Synthesis of oxathiane and morpholine from acyclic precursors: A modified Mitsunobu reaction

Synthesis of a set of isomeric 2,4,6-triarylmorpholines and 2,6-diaryloxathianes from the corresponding 1,5-diols has been described. The method provides an efficient route to six-membered heterocycles from acyclic diols and is found to be better than Mitsunobu procedure in yield and waste management. In a related study, the ring contraction of pyranone to two isomeric cyclopentenone derivatives through Nazarov reaction has been noticed.

Synthesis, stereochemistry, antimicrobial evaluation and QSAR studies of 2,6-diaryltetrahydropyran-4-one thiosemicarbazones

A series of 2,6-diaryltetrahydropyran-4-one thiosemicarbazones (11-27) were synthesized and characterized for evaluation of potential antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, Bacillu

Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles

Three series of oxime ethers viz, 2,6-diarylpiperidin-4-one O-benzyloximes 5a-o, 2,6-diaryltetrahydropyran-4-one O-benzyloximes 7a-e and 2,6-diaryltetrahydrothiopyran-4-one O-benzyloximes 11a-b and 12a-c were synthesized and stereochemistry is established by their spectral and single crystal analysis. A SAR study has been carried out for the above oxime ethers against a panel of antibacterial (Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Escherichia coli) and antifungal agents (Candida albicans, Candida-51, Rhizopus sp., Aspergillus niger, Aspergillus flavus and Cryptococcus neoformans), respectively, using Ciprofloxacin and Amphotericin B as standards. Most of the chloro/methyl/methoxy substituted compounds exerted moderate to good activity against all the tested organisms; moreover, some compounds (5i, 5l, 5n, 5o, 7c2, 7d1, 7d2, 7e, 11b and 12c) exhibited promising activity than standard drugs.

Reactivity of Some Epimeric 4-Aminooxanes towards Oxidation by Cerium(IV)

Kinetics of oxidation of four epimeric pairs of 4-aminooxanes by Ce(IV) in aqueous acetic acid in the presence of nitric acid, have been investigated.The oxidation is first order in .No definite order exists with respect to .A mechanism involving the abstraction of a H-atom from the α-C-H by Ce(IV) in the rate-limiting step is proposed.Equatorial amines react faster than axial amines.Added H(+) or NO3(-) increase the rate of oxidation.Rate is lowered by increase in the polarity of the medium.The conformational (steric) and electronic effects on the rate of oxidation are discussed.

Dissociation Constants of Cyanohydrins of Some Tetrahydropyran-4-ones

The dissociation constants of cyanohydrins of some substituted tetrahydropyran-4-ones have been determined at 30 deg in 80percent dioxane-water (v/v).The results substantiate the steric environment of the carbonyl group in these ketones.

Cycloalkanones. 9. Comparison of analogues which inhibit cholesterol and fatty acid synthesis

A number of 2,8-dibenzylcyclooctanone analogues inhibited the HMG-CoA reductase activity of Holtzman male rat liver, whereas only 2-octanone, 2-hexadecanone, 2,8-dibenzyl cyclooctanone derivatives, and 2 bis (4 chlorophenyl) 3,5 dimethyl tetrahydro 4 pyrone inhibited fatty acid synthetase activity. 2-Octanone significantly lowered serum cholesterol, triglycerides, and glycerol levels in Holtzman male rats and serum cholesterol in male CF1 mice. Serum lipase activity was significantly elevated in rats administered 20 mg/kg/day of 2-octanone for 16 days. The activity of liver HMG-CoA reductase was inhibited in mice administered 10 mg/kg/day of 2-octanone for 10 days and in mouse and rat liver in vitro by 10 mg of 2-octanone. In mice, fecal excretion of [14C]cholesterol and tripalmitin was accelerated whereas palmitic acid and cholesteryl oleate were not affected by 10 mg/kg/day of 2-octanone. The LD50 in male mice for 2-octanone was 1.6 g/kg.