17159-75-0

Usage

Uses

Used in Pharmaceutical Industry:
Bicyclo[3.1.1]heptan-3-one is used as a starting material for the synthesis of various pharmaceuticals due to its unique bicyclic structure and reactivity, contributing to the development of new drugs and medicinal compounds.
Used in Flavor and Fragrance Industry:
In the food industry, Bicyclo[3.1.1]heptan-3-one is utilized as a flavoring agent, specifically in the production of baked goods and confectionery, to impart a distinctive aroma and taste.
Safety Considerations:
It is crucial to handle Bicyclo[3.1.1]heptan-3-one with care due to its flammable nature and potential to cause irritation to the skin, eyes, and respiratory system upon contact. Proper safety measures should be implemented during its use in both industrial and laboratory settings.

Upstream product

• 73991-26-1 bicyclo<2.1.1>-2-dibromomethylhexan-2-ol 
• 89448-34-0 2-aminomethylbicyclo<2.1.1>hexan-2-ol 
• 77079-11-9 endo-1-methoxy-2-norbornylamine 

Relevant academic research and scientific papers

Regioselectivity in Ring-Expansion of 1-Substituted Bicyclohexan-2-ones: Preferential Migration of Methylene Over Bridgehead Carbon

Ring expansion of several 1-substituted bicyclohexan-2-ones has been investigated in order to compare the effect od substitution on the migratory aptitude of the bridgehead carbon in relation to the methylene carbon.In the cases examined it was observed that there is a marked preference for migration of the methylene carbon, with the substituted substrates displaying higher regioselectivity that the parent ketone.In the rearrangement of both 1-fluoro- and 1-chloro-bicyclohexan-2-one, migration of the methylene carbon occurs exclusively.

Desaminierungsreaktionen, 34. Diels-Alder-Reaktionen mit Methoxycyclopentadien, ein Weg zu 1-Methoxynorbornan-2-diazonium-Ionen

A mixture of 1- and 2-methoxycyclopentadiene (7, 8) was prepared in four steps from cyclopentadiene.Diels-Alder reaction of 7 + 8 with methyl acrylate produces a mixture of adducts from which the 1-methoxy isomers (9, 11) were obtained by distillation.Separation by way of the iodo lactone 20, hydrogenation, and Curtius degradation afforded endo- and exo-1-methoxy-2-norbornylamine (14, 17).Nitrous acid deamination of 14 yielded norpinan-2-one (21) and norbornan-2-one (22) in a 3:7 ratio whereas 17 gave 22 only.The results of the deamination reactions confirm the position of the methoxy groups and illustrate the superiority of diazonium precursors in the norbornane - norpinane rearrangement.