89398-16-3

Upstream product

• 80-63-7 methyl 2-chloroacrylate 
• 1192-37-6 methylenecyclohexane 

Downstream Products

• 89414-11-9 α-Hydroxy-1-cyclohexene-1-butanoic Acid 
• 89398-24-3 (Z)-1-Cyclohexene-1-propanal Oxime 
• 89398-17-4 1-Cyclohexene-1-propanal Oxime 
• 89398-18-5 N-Hydroxy-1-cyclohexene-1-propanamine 
• 16783-22-5 cis-octahydro-1H-inden-1-one 
• 16783-22-5 trans-1-hexahydroindanone 
• 13992-93-3 3-(cyclohex-1-en-1-yl)propan-1-amine 
• 669714-92-5 2-(3-cyclohex-1-enyl-1-phenylsulfanyl-propyl)-3-hydroxy-cyclopent-2-enone 
• 669714-93-6 acetic acid 2-(3-cyclohex-1-enyl-propyl)-3-oxo-cyclopent-1-enyl ester 
• 669714-94-7 2-(3-cyclohex-1-enyl-propyl)-3-hydroxy-cyclopent-2-enone 
• 60416-25-3 3-(cyclohex-1-enyl)propionaldehyde 

Relevant academic research and scientific papers

Total Synthesis of (+/-)-Nitramine. Development of a Ketene Equivalent in the Ene Reaction

(+/-)-Nitramine (1a) was synthesized in seven steps from methylenecyclohexane in 33percent overall yield.A three-step sequence was developed from methylenecyclohexane to aldehyde 4 in which methyl α-chloroacrylate was used as a ketene equivalent in the ene reaction.Aldehyde 4 was converted to nitrone 3 which cyclized to a 2.5:1 mixture of 2 and 9.Hydrogenolysis of 2 gave 1a.Lewis acid catalyzed cyclization of 4 gave a 3.5:1 mixture of hydrindanones 13 and 14 at 25 deg C and a 12:1 mixture of 13 and 14 at -20 deg C.

Intramolecular [2+2] photocycloaddition-fragmentation: Facile entry to a novel tricyclic 5-6-7 ring system

An expeditious route to a novel 5-6-7 tricyclic ring system is described. The chemistry capitalizes on an enantioselective glyoxylate-ene reaction, enzymatic resolution as well as a [2+2] photocycloaddition-fragmentation.