16868-65-8

Usage

Chemical Class

Ketones

Usage

Manufacturing of pharmaceuticals and pesticides

Potential Applications

Organic synthesis and medicinal chemistry

Reactivity

Highly reactive due to the presence of the propynyl group

Suitability

Wide range of chemical reactions

Biological Activities

Antimicrobial and antifungal properties

Field of Research

Chemical research and development

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 106-96-7 propargyl bromide 
• 69948-55-6 3-(2,2-dimethylhydrazino)cyclohex-2-en-1-one 

Downstream Products

• 54244-73-4 2-n-propyl-1,3-cyclohexanedione 
• 210172-25-1 3-methoxy-2-(2-propynyl)-cyclohex-2-en-1-one 
• 93007-96-6 1-benzyl-2-methyl-1,5,6,7-tetrahydro-4H-indol-4-one 
• 72211-20-2 2-methyl-1-phenyl-1,5,6,7-tetrahydro-4H-indol-4-one 
• 1265166-83-3 3-(phenylamino)-2-(prop-2-ynyl)cyclohex-2-enone 
• 92425-80-4 1-(4-chlorophenyl)-2-methyl-5,6-dihydro-1H-indol-7(4H)-one 
• 326916-10-3 2-methyl-1-(p-tolyl)-6,7-dihydro-1H-indol-4(5H)-one 
• 50615-16-2 2-methyl-6,7-dihydro-5H-benzofuran-4-one 
• 1210056-56-6 2-(3-oxobutyl)-2-(prop-2-yn-1-yl)cyclohexane-1,3-dione 

Relevant academic research and scientific papers

Synthesis of tetrahydrobenzo[b]furans via a gold(I)-catalyzed rearrangement/cycloisomerization sequence of cyclic 1-aryl-2-propargyl-cyclohex-2enols

A facile synthesis of tetrahydrobenzo[b]furans via gold(I)-catalyzed cycloisomerization of 1-aryl-2-propargylcyclohex-2-enols is described. The transformation is suggested to proceed through a gold(I)-catalyzed tertiary allylic alcohol rearrangement to gi

Organocatalytic Reductive Propargylation: Scope and Applications

An amino acid-catalyzed three-component reductive coupling protocol has been developed for the selective high-yielding synthesis of nearly fifty examples of propargylated cyclic/acyclic systems from the various propargyl aldehydes, cyclic/acyclic CH acids, and Hantzsch ester under ambient conditions. It is an economical, efficient, catalytic, metal-free protocol for the quick gram-scale synthesis of propargylated cyclic/acyclic compounds, and many of these coupling compounds were purified by a simple precipitation-filtration technique instead of column chromatography. Functionally rich propargylated cyclic-1,3-diketones were specifically transformed into dihydropyrans found in natural products and drugs through an annulative etherification reaction by using Lewis-acid (AgOTf) catalysis. Further, we developed the C-methylation reactions on propargylated cyclic-1,3-diketones, which are prolific synthons in natural products and medicinal chemistry.

Asymmetric Synthesis of Carbocyclic Propellanes

A modular synthesis of functionalized carbocyclic propellanes was developed. Formation of the first of two quaternary bridgehead centers has been achieved by desymmetrization of prostereogenic ketones by either Hajos-Parrish-Eder-Sauer-Wiechert-type processes or Werner’s catalytic asymmetric Wittig reaction. The obtained bicyclic enones were subjected to conjugate additions upon which the remaining ring was formed by olefin metathesis. All bridges are amenable to further derivatization, which renders those compounds useful as central units in fragment-based drug discovery or as ligand scaffolds.

Regioselective alkylations of cyclic 1,3-diketones via metalated dimethylhydrazones

Cyclic 1,3- diketones 1 are transformed into their 2,2-dimethylhydrazones 2, which can be alkylated regioselectively at different positions after mono-, di-, tri-, and tetrametalation. Monometalated C-2 unsubstituted hydrazones afford C-2 and N- alkylation, monometalated C-2 substituted hydrazones afford only C-2 alkylation.The regioselectivity of the alkylation of the polymetalated hydrazones follows Hauser's rule according to the sequence: NH- > C-4 Ha > C-5 > C-4 Hb. Hydrolysis of the product hydrazones 3-5 afforded mono- and polyalkylated 1,3- diketones 7 in good yields.