133436-06-3

Upstream product

• 20452-75-9 exo-7-chloro-endo-7-phenylbicyclo<3.2.0>hept-2-en-6-one 
• 133436-04-1 5-(diethylamino)-7-phenylbicyclo<3.2.0>hept-2-en-6-one 
• 74-88-4 methyl iodide 

Downstream Products

• 133436-07-4 2-(diethylamino)-7-methyl-7-phenylcyclohepta-2,4-dien-1-one 

Relevant academic research and scientific papers

Synthesis of 5-Methoxy- and 5-(Dialkylamino)bicyclohept-2-en-6-one Derivatives by cine Substitution with Methoxide Anions and Dialkylamines

exo-7-Chloro-endo-7-phenylbicyclohept-2-en-6-one (5) undergoes cine substitution reactions with methoxide anions and with dialkylamines to give 5-methoxy or 5-dialkylamino derivatives 13, 14, 16-19 in high yield.While attempts directed to an acetalization have failed, the addition of Grignard reagents to the methoxy derivatives proceeds stereoselectively in high yield.Hydrochlorides 20/21 lose amine at 110 deg C to form 2-phenyltropone (22).Thermolysis of diethylamino derivative 24 at 170 deg C (temperature determined by DSC) results in the formation of the dienoaminone 25. - Key Words: Bicyclohept-2-en-6-one, cine substitution / DSC

5-Substituted Bicyclohept-2-en-6-ones: Synthesis and Ring-opening Reactions

5-Methoxy- and 5-dialkylamino-bicyclohept-2-en-6-one derivatives 2 and 3 are formed in high yield by cine substitution at the fused exo-chlorocyclobutanone 1, subsequent reactions yielding 2-phenyltropone 6 and a cycloheptadienone enamine 8.