67263-02-9

Basic information

• Product Name: Cyclohexanone, 3-(dimethylphenylsilyl)-3,5,5-trimethyl-
• CAS NO: 67263-02-9
• Molecular Formula: C17H26OSi
• Molecular Weight: 274.478
• Mol File: 67263-02-9.mol

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, 3-(dimethylphenylsilyl)-3,5,5-trimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 3-(dimethylphenylsilyl)-3,5,5-trimethyl-(67263-02-9)
• EPA Substance Registry System: Cyclohexanone, 3-(dimethylphenylsilyl)-3,5,5-trimethyl-(67263-02-9)

Safety Data

• Hazardous Substances Data: 67263-02-9(Hazardous Substances Data)

Upstream product

• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 768-33-2 phenyldimethylsilyl chloride 
• 3839-31-4 dimethyl(phenyl)silyllithium 

Relevant articles and documents

Copper-catalyzed conjugate addition of a bis(triorganosilyl) zinc and a methyl(triorganosilyl) magnesium

A practical copper-catalyzed conjugate silylation of α,β- unsaturated carbonyl compounds 4 utilizing bis(triorganosilyl) zinc reagent 3 is described. Moreover, mixed methyl(triorganosilyl) magnesium 7 also transfers its silyl ligand to simple enones 4 und

Conjugate addition of dimethylphenylsilyllithium to α,β-unsaturated carbonyl compounds mediated by sub-stoichiometric quantities of dimethylzinc

Dimethylphenylsilyllithium undergoes conjugate addition to a variety of α,β-unsaturated enones in the presence of sub-stoichiometric amounts of dimethylzinc. Down to 10 mol % of Me2Zn facilitates these reactions to afford good to excellent yields of β-silylated products. This catalytic behavior is displayed when the Me2Zn used is generated in situ, from the addition of methyllithium to zinc (II) iodide or when used directly from a commercial source. This methodology in which sub-stoichiometric quantities of the reactive organometallic reagent are present at a given time may provide a route for catalytic enantioselective conjugate addition of trialkylsilyl moieties to enones.

Conjugate Addition of the Phenyldimethylsilyl Group to αβ-Unsaturated Carbonyl Compounds Using a Silylzincate in Place of the Silylcuprate

Lithium phenyldimethylsilyl(dialkyl)zincates add to a number of αβ-unsaturated carbonyl compounds to give, in most cases, higher yields of the conjugate addition product than we had achieved with the corresponding silylcuprate.

The Conjugate Addition of a Silyl Group to Enones and its Removal with Copper(II) Bromide: A Protecting Group for the αβ-Unsaturation of αβ-Unsaturated Ketones

Silyl-lithium reagents mixed with copper(I) salts react with enones, including esters and aldehydes, to give β-silyl carbonyl compounds in good yield.The β-silylketones can be used in synthesis without risk to the silyl group and the enone group can be restored by bromination-desilylbromination with copper(II) bromide.The principle is illustrated with syntheses of carvone and dihydrojasmone.