122847-20-5

Basic information

• Product Name: 1-(1-Cyclohexenyl)-3-hydroxy-1-butanone
• CAS NO: 122847-20-5
• Molecular Weight: 168.236
• Mol File: 122847-20-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(1-Cyclohexenyl)-3-hydroxy-1-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-Cyclohexenyl)-3-hydroxy-1-butanone(122847-20-5)
• EPA Substance Registry System: 1-(1-Cyclohexenyl)-3-hydroxy-1-butanone(122847-20-5)

Safety Data

• Hazardous Substances Data: 122847-20-5(Hazardous Substances Data)

Upstream product

• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 75-07-0 acetaldehyde 
• 932-66-1 1-cyclohexenyl methyl ketone 
• 5111-47-7 (R/S)-1-(3-hydroxybut-1-yn-1-yl)-cyclohexanol 

Downstream Products

• 91897-80-2 1-(1'-cyclohexenyl)-2-buten-1-one 
• 101183-94-2 (3α,4β,4aα,8aα)-4-(1-Cyclohexenylcarbonyl)-3-methyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one 

Relevant articles and documents

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.