28017-80-3

Basic information

• Product Name: 2-Cyclohexen-1-one, 3-(1,1-dimethylethyl)-5,5-dimethyl-
• CAS NO: 28017-80-3
• Molecular Formula: C12H20O
• Molecular Weight: 180.29
• Mol File: 28017-80-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 3-(1,1-dimethylethyl)-5,5-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 3-(1,1-dimethylethyl)-5,5-dimethyl-(28017-80-3)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 3-(1,1-dimethylethyl)-5,5-dimethyl-(28017-80-3)

Safety Data

• Hazardous Substances Data: 28017-80-3(Hazardous Substances Data)

Upstream product

• 6267-39-6 3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one 
• 2259-30-5 tert-butylmagnesium bromide 
• 13271-49-3 3-bromo-5,5-dimethlycyclohex-2-en-1-one 
• 594-19-4 tert.-butyl lithium 
• 849595-89-7 3-(butyltellanyl)-5,5-dimethyl-cyclohex-2-enone 
• 80534-76-5 diethyl 5,5-dimethyl-3-oxocyclohex-1-enyl phosphate 
• 126-81-8 dimedone 

Downstream Products

• 122902-91-4 2-methoxy-4,4-dimethyl-6-tert-butylcyclohexa-2,5-diene-1-one 
• 122800-85-5 2-hydroxy-4,4-dimethyl-6-tert-butylcyclohexa-2,5-diene-1-one 
• 122800-93-5 3-tert-Butyl-6-hydroxy-5,5-dimethyl-5,6-dihydro-pyran-2-one 
• 77426-44-9 2-Allyloxy-3-tert-butyl-5,5-dimethyl-cyclohex-2-enone 

Relevant articles and documents

Diastereoselective synthesis of α,β-unsaturated systems

Functionalized Z-vinylic tellurides were used in substitution reactions with lower order cyanocuprates leading to α,β-unsaturated ketones and esters in good yields. In the case of acyclic tellurides, the product was obtained in high diastereoselectivity. The control of the stereoselectivity was achieved by simple change of the reaction temperature.

Reaction of β-halo α,β-unsaturated ketons with cuprate reagents. Efficient syntheses of β,β-dialkyl ketones and β-alkyl α,β-unsaturated ketones. A synthesis of (Z)-jasmone

Treatment of the 3-halo-2-cyclohexen-1-ones 11-15 and 17 with an excess of lithium dimethylcuprate provided good to excellent yields of the corresponding 3,3-dimethylcyclohexanones 21-24.Similar reactions involving the β-bromo cyclopentenones 19 and 20 stopped at the monoaddition stage, producing the cyclopentenones 40 and 43.Reaction of the β-bromo cyclohexenones 12 and 15 with 1.1 equiv. of lithium dimethylcuprate did not effect clean conversion of these substrates into the corresponding 3-methyl-2-cyclohexen-1-ones.When a series of β-bromo enones 12, 14-19were allowed to react with the lithium (phenylthio)(alkyl)cuprates 44-47, the correspondig β-alkyl enones were, in general, produced cleanly and efficiently.However, reaction of 3-bromo-2-methyl-2-cyclopenten-1-one (19) with the cuprate reagent 44 gave mainly the β-phenylthio enone 49.This undesired result could be avoided by employing, in the place of 19, The β-iodo cyclopentenone 50, which reacted smoothly with 44 to give a high yield of 2,3-dimethyl-2-cyclopenten-1-one (40).Reaction of 3-bromo-2-cyclohexen-1-one (14) with 3 equiv. of the mixed vinylcuprate reagent 48 gave 3-(3-butenyl)-2-cyclohexen-1-one (32).Alkylation of 1,3-cyclopentanedione with (Z)-1-chloro-2-pentene afforded compound 51, which was converted into the β-bromo enone 52.Treatment of the latter substance with lithium dimethylcuprate provided (Z)-jasmone (53).