74272-34-7

Upstream product

• 932-66-1 1-cyclohexenyl methyl ketone 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 122847-21-6 1-(1-Cyclohexenyl)-3-hydroxy-3-methyl-1-butanone 
• 15332-41-9 4-(cyclohex-1-en-1-yl)-2-methylbut-3-yn-2-ol 
• 61892-19-1 cyclohexanone benzenesulfonylhydrazone 

Relevant academic research and scientific papers

1,4-Pentadien-3-ones, 31. 1-(1-Cyclohexenyl)-1-propen-2-ones: Synthesis, Properties, and Stereoselective Formation of 3-Aryl-4-(1-cyclohexenylcarbonyl)perhydro-1-naphthalenones by Sequential Michael Reaction

On rearrangement, 1-ethynyl-1-cyclohexanol (1) yields 1-acetyl-1-cyclohexene (2).At -78 deg C in the presence of LDA, 2 reacts with aldehydes/ketones yielding the aldols 5/8, which are dehydrated to the title compounds 6 or 9.At room temp., a reaction between the lithium derivative of 2 and 6 ensues, yielding the bicyclic products 10.These can also be prepared independently from isolated 6 and 2 with LDA or butyllithium in high yields.The stereochemistry is elucidated by spectroscopic methods, and the minimum energy conformation of 10a is calculated.Thestereoselective formation of 10 is explained by a lithium-controlled sequential Michael reaction.

Silanes in Organic Synthesis. 8. Preparation of Vinylsilanes from Ketones and Their Regiospecific Cyclopentenone Annulation

A general method is described for the formation of vinylsilanes from ketones.Thus, conversion to the benzene- or p-toluenesulfonylhydrazone and sequential treatment with n-butyllithium and chlorotrimethylsilane in anhydrous tetramethylethylenediamine proceeds regiospecifically to afford the less substituted vinylsilane (in unsymmetrical cases).Friedel-Crafts acylation with acryloyl chlorides and aluminium chloride and subsequent Nazarov cyclization with Lewis acid catalysis results in cyclopentenone annulation.Numerous examples that reveal the scope of this processare described.Due to accompanying polymerization, annulation with acryloyl chloride itself is least efficient.This complication can, however, be averted through use of β-chloropropionyl chloride and dehydrochlorination with 1,5-diazabicycloundec-5-ene prior to ring closure.