89337-63-3

Usage

Functional groups

Ester, Cyclohexene, Carboxylic acid, Methyl, and Oxo

Structure

A cyclohexene ring with a carboxylic acid group at position 1, a methyl group at position 2, and an oxo group at position 6, with an ethyl ester group attached to the carboxylic acid.

Appearance

Colorless to pale yellow liquid

Density

1.1 g/cm3 (approximate)

Boiling point

280°C (approximate)

Melting point

Not available, as it is a liquid at room temperature

Solubility

Soluble in organic solvents like ethanol, methanol, and acetone

Uses

a. Flavoring agent in the food industry
b. Intermediate in the synthesis of biologically active compounds and drugs
c. Potential pharmaceutical applications

Properties

a. Antimicrobial activity
b. Antioxidant properties

Safety

Handle with care, as it may cause irritation or other adverse effects if not used properly

Storage

Store in a cool, dry, and well-ventilated area, away from heat and open flames

Regulatory status

Its use as a flavoring agent is regulated by the FDA and other international food safety organizations

Synonyms

Ethyl 2-methyl-6-oxo-1-cyclohexene-1-carboxylate, Ethyl 2-methyl-6-oxocyclohex-2-ene-1-carboxylate

Chemical classification

Aromatic ester, Cyclic ester, and Heterocyclic ester

Upstream product

• 1071-46-1 hydrogen ethyl malonate 
• 3128-06-1 5-ketohexanoic acid 
• 1000014-37-8 ethyl 3-oxooct-7-ynoate 

Relevant academic research and scientific papers

Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enones to Chiral Cycloalkanols with Three Contiguous Stereocenters

A highly efficient iridium-catalyzed asymmetric hydrogenation of tetrasubstituted cyclic enones has been developed for the enantioselective synthesis of chiral cycloalkanols with three contiguous stereocenters. The C=O and C=C bonds of the enone substrate

Vinylogous Reactivity of Cyclic 2-Enones: Organocatalysed Asymmetric Addition to 2-Enals to Synthesize Fused Carbocycles

A method for asymmetric and site selective annulations at the γ and γ′ positions of cyclic 2-enones with α,β-unsaturated aldehydes has been developed. The organocatalysed [3+3]-annulations proceed with high levels of regio-, diastereo-, and enantioselectivity, affording a series of high value fused carbocycles. Further elaboration gave key lactones (both bridged and fused).

Yb(OTf)3-promoted ZnCl2-catalyzed conia-ene reaction of linear β-alkynic β-dicarbonyls

An atom-economical and solvent-free ytterbium(III) triflate promoted, zinc(II) chloride catalyzed Conia-ene method has been developed for the construction of five- to six-membered-ring carbocycles. In the presence of zinc(II) chloride and ytterbium(III) triflate, a variety of linear β-alkynic β-keto esters and -alkynic -diketones were cyclized under neat conditions in moderate to good yields. It is noteworthy that the selectivity toward five- or six-membered-ring carbocycles depends on substituents at the terminal alkynes. Georg Thieme Verlag Stuttgart.

Efficient formation of ring structures utilizing multisite activation by indium catalysis

Lewis acidic indium(III) salts, in particular In(NTf2) 3, effect the conversion of α-(ω′-alkynyl)-β- ketoesters and ω-alkynyl-β-ketoesters to the corresponding cyclic products in a manner known as the Coniaene reaction. This reaction

Indium-catalyzed cycloisomerization of ω-alkynyl-β-ketoesters into six- to fifteen-membered rings

(Chemical Equation Presented) Many different sizes of rings available: Heating ω-alkynyl-β-ketoesters in the presence of In(NTf 2)3 (Tf=trifluoromethanesulfonyl) produces six- to fifteen-membered ring products in good yields. The reaction features low catalyst loading and moderately dilute conditions, and the formation of medium-sized rings is sometimes faster than that for the corresponding six-membered rings. A synthesis of (±)-muscone is also reported.

A synthetic approach to Benanomicin A. 2. Synthesis of the substituted 5,6-dihydrobenzo[a]naphthacenequinone

The key intermediate tri-substituted α-tetralone (8) has been synthesized, either via tandem MICHAEL addition-DIECKMANN condensation reaction between dienolate and methyl crotonate in a low yield or via BARTON'S radical decarboxylation of diester (9) with