113344-48-2

Upstream product

• 106-38-7 para-bromotoluene 
• 927-74-2 3-Butyn-1-ol 
• 96-48-0 4-butanolide 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 29480-08-8 1-(4-methylphenyl)cyclobutan-1-ol 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 107840-88-0 2,2-simethyl-1,3-oxathiane 3,3-dioxide 

Downstream Products

• 199329-49-2 4-Iodo-1-(4-methylphenyl)-1-butanone 
• 62506-81-4 4-oxo-4-(p-tolyl)butanal 
• 247215-99-2 phenyl-carbamic acid 4-oxo-4-p-tolyl-butyl ester 

Relevant academic research and scientific papers

Sequential multicomponent catalytic synthesis of pyrrole-3-carboxaldehydes: Evaluation of antibacterial and antifungal activities along with docking studies

A sequential multicomponent synthesis of highly substituted pyrrole-3-carboxaldehydes has been developed under metal-free conditions. This one-pot protocol involves proline-catalyzed direct chemoselective Mannich reaction-cyclization between 1,4-ketoaldehyde and in situ generated Ar/HetAr-imines followed by aerobic oxidative-aromatization at room temperature. A series of fully substituted pyrrole-3-carboxaldehydes and other diverse fused heterocycles have been synthesized. These compounds were tested for in vitro antibacterial and antifungal activities, and the selected ones display significant activity against the tested bacterial strains with a MIC value of 16 μg mL-1, which is close to that of the standard drug chloramphenicol. The bioactivity outcome was further analyzed using docking studies.

Cyclic ether synthesis from diols using trimethyl phosphate

Cyclic ethers have been effectively synthesized via the intramolecular cyclization of diols using trimethyl phosphate and NaH. The present cyclization could proceed at room temperature to produce 5-7 membered cyclic ethers in good to excellent yields. Substrates possessing a chiral secondary hydroxy group were transformed into the corresponding chiral cyclic ethers along with the retention of their stereochemistries.

Catalytic asymmetric intramolecular homologation of ketones with α-diazoesters: Synthesis of cyclic α-Aryl/Alkyl β-ketoesters

A catalytic asymmetric intramolecular homologation of simple ketones with α-diazoesters was firstly accomplished with a chiral N,N′-dioxide-Sc(OTf)3 complex. This method provides an efficient access to chiral cyclic α-aryl/alkyl β-ketoesters containing an all-carbon quaternary stereocenter. Under mild conditions, a variety of aryl- and alkyl-substituted ketone groups reacted with α-diazoester groups smoothly through an intramolecular addition/rearrangement process, producing the β-ketoesters in high yield and enantiomeric excess.

Phenyliodine diacetate-mediated oxidative cleavage of cyclobutanols leading to γ-hydroxy ketones

Oxidative cleavage of cyclobutanols using PIDA, which leads to efficient entry of γ-hydroxy ketones, is described. When using 2-substituted cyclobutanols, γ-substituted γ-hydroxy ketones are obtained through regioselective C-C bond cleavage.

Hydroxyarylketones via Ring-Opening of lactones with aryllithium reagents: An expedient synthesis of ( )-anabasamine

The regioselective ring-opening of lactones (δ-valerolactone and γ-butyrolactone) with aryllithium reagents is reported for the construction of a series of δ-hydroxy aryl ketones and γ-hydroxy aryl ketones. Application of this method for the expeditious syntheses of ( )-anabasamine and its nicotine-related analogue are also described.

Regioselective synthesis of 4-substituted-1-aryl-1-butanones using a Sonogashira-hydration strategy: Copper-free palladium-catalyzed reaction of terminal alkynes with aryl bromides

A simple one-pot procedure has been developed for the synthesis of 4-substituted-1-aryl-1-butanones through copper-free Sonogashira reaction of aryl bromides with terminal alkynes in DMF under inert atmosphere, followed by the treatment with acid in the p

2,2-Dimethyl-1,3-oxathiane 3,3-dioxide: A γ-hydroxypropyl anion equivalent

The reaction of 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide with various electrophiles is presented. Acylation of the anion provided labile 4-acyl-2,2-dimethyl-1,3-oxathiane 3,3-dioxides which underwent desulfonation with silica gel to produce γ-hydroxy ketones with three carbon unit elongation. Thus, 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide was shown to be a useful synthetic equivalent of a γ-hydroxypropyl anion. Methyl esters proved to be the best acylating agents in this reaction. Synthetic utility of this carbon chain elongation was illustrated by the syntheses of dl-lanceol and dl-dihydrojasmone.

A New Method for the Preparation of γ-Hydroxy Ketones: a Formal Total Synthesis of (+/-)-Lanceol

The reaction of methyl esters with 2,2-dimethyl-4-lithio-1,3-oxathiane 3,3-dioxide followed by treatment with silica gel affords γ-hydroxy ketones.