57576-14-4

Usage

Physical state

Colorless liquid

Odor

Sweet, fruity

Usage

Manufacturing of fragrances and flavors

Application

Reagent in organic synthesis

Production

Pharmaceutical production

Role

Building block in the synthesis of various chemical compounds

Ability

Acts as a chiral auxiliary in asymmetric synthesis

Industries

Chemical and pharmaceutical

InChI:InChI=1/C11H17N/c1-9-5-4-7-11(2,3)10(9)6-8-12/h5,10H,4,6-7H2,1-3H3

Upstream product

• 79857-84-4 (3E)-8-hydroxy-4,8-dimethyl-3-nonenenitrile 
• 51332-89-9 Cyclogeranyl methanesulfonate 
• 143-33-9 sodium cyanide 
• 57576-16-6 (3E)-7-bromo-8-hydroxy-4,8-dimethyl-3-nonenenitrile 

Downstream Products

• 472-64-0 (2,6,6-Trimethyl-2-cyclohexenyl)acetaldehyde 
• 472-67-3 (2,6,6-Trimethyl-2-cyclohexenyl)acetic acid 

Relevant academic research and scientific papers

Limonoid model insect antifeedants. A stereoselective synthesis of azadiradione C, D, and E fragments through intramolecular diazo ketone cyclization

A stereoselective synthesis of model compound 18 of the insect antifeedant azadiradione has been accomplished starting from α-cyclocitral in 12 steps in 15% overall yield. The strategy for the synthesis is based on an intramolecular cyclopropanation of a diazo ketone and subsequent selective cleavage of a cyclopropyl ketone. Reactivity differences in the cleavage of the key cyclopropyl ketone 13 and its homolog 12 lacking the furyl ring are explored.

CATIONIC CYCLIZATION OF GERANONITRILE AND RELATED COMPOUNDS VIA THEIR BROMOHYDRINS: APPLICATION TO THE SYNTHESIS OF (+/-)-SNYDEROLS

Cationic cyclization of bromohydrins of geranonitrile and homogeranonitrile in the presence of boron trifluoride complexes proceeded smoothly, giving mixtures of bromo cyclic olefins in satisfactory yields.This cyclization method was applied to the synthesis of (+/-)-snyderols.