2206-69-1

Usage

Also Known As

exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-5-one

Structure

Bicyclic with a unique six-membered ring

Type of Compound

Ketone

Aroma

Strong, sweet, and slightly fruity

Uses

a. Flavoring agent in food and beverages
b. Manufacturing of perfumes and fragrances
c. Ingredient in cosmetic and fragrance industries
d. Production of soaps, detergents, and other household products

Value

Valuable and widely used due to its unique and versatile properties

InChI:InChI=1/C12H18O/c1-7-8(2)11(5)10(3,4)12(11,6)9(7)13/h1-6H3

Upstream product

• 3854-96-4 2,3,4,5,6,6-hexamethylcyclohexa-2,4-dien-1-one 

Downstream Products

• 3043-52-5 1,2,3,3,4,5-hexamethyl-6-methylene-cyclohexa-1,4-diene 
• 87-85-4 Hexamethylbenzene 
• 4045-44-7 1,2,3,4,5-pentamethylcyclopentadiene 
• 53857-77-5 1,1,3,4,5,6-hexamethyl-2-hydroxybenzenonium ion 

Relevant academic research and scientific papers

Lewis Acid Catalyzed Enantioselective Photochemical Rearrangements on the Singlet Potential Energy Surface

The oxadi-methane rearrangement of 2,4-cyclohexadienones to bicyclic ketones was found to proceed with high enantioselectivity (92-97% ee) in the presence of catalytic amounts of a chiral Lewis acid (15 examples, 52-80% yield). A notable feature of the transformation is the fact that it proceeds on the singlet hypersurface and that no triplet intermediates are involved. Rapid racemic background reactions were therefore avoided, and the catalyst loading could be kept low (10 mol %). Computational studies suggest that the enantioselectivity is determined within a Lewis acid bound singlet intermediate via a conical intersection. The utility of the method was demonstrated by a concise synthesis of the natural product trans-chrysanthemic acid.