71820-49-0

Usage

α,β-unsaturated ketone

A type of carbonyl compound containing both a carbonyl group (C=O) and a carbon-carbon double bond (C=C) in its structure.

Fragrant properties

Used as a fragrance ingredient in perfumes and personal care products, providing floral, fruity, and citrusy scents to the final product.

Flavoring agent

Utilized in food products and beverages to impart unique and desirable flavors.

Chemical production

Serves as a key component in the synthesis of other chemicals, including pharmaceuticals and agrochemicals.

Potential irritation

Careful handling is required, as 1-Phenyl-2-ethyl-1-hexene-3one can cause skin, eye, and respiratory system irritation.

InChI:InChI=1/C14H18O/c1-3-8-14(15)13(4-2)11-12-9-6-5-7-10-12/h5-7,9-11H,3-4,8H2,1-2H3/b13-11+

Upstream product

• 123-19-3 4-heptanone 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Site- and Enantioselective Iridium-Catalyzed Desymmetric Mono-Hydrogenation of 1,4-Dienes

The control of site selectivity in asymmetric mono-hydrogenation of dienes or polyenes remains largely underdeveloped. Herein, we present a highly efficient desymmetrization of 1,4-dienes via iridium-catalyzed site- and enantioselective hydrogenation. This methodology demonstrates the first iridium-catalyzed hydrogenative desymmetriation of meso dienes and provides a concise approach to the installation of two vicinal stereogenic centers adjacent to an alkene. High isolated yields (up to 96 %) and excellent diastereo- and enantioselectivities (up to 99:1 d.r. and 99 % ee) were obtained for a series of divinyl carbinol and divinyl carbinamide substrates. DFT calculations reveal that an interaction between the hydroxy oxygen and the reacting hydride is responsible for the stereoselectivity of the desymmetrization of the divinyl carbinol. Based on the calculated energy profiles, a model that simulates product distribution over time was applied to show an intuitive kinetics of this process. The usefulness of the methodology was demonstrated by the synthesis of the key intermediates of natural products zaragozic acid A and (+)-invictolide.