106543-48-0

Basic information

• Product Name: 4-Phenyl-4-(trimethylsiloxy)butansaeure-methylester
• Synonyms: 4-Phenyl-4-(trimethylsiloxy)butansaeure-methylester
• CAS NO: 106543-48-0
• Molecular Weight: 266.412
• Mol File: 106543-48-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-Phenyl-4-(trimethylsiloxy)butansaeure-methylester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenyl-4-(trimethylsiloxy)butansaeure-methylester(106543-48-0)
• EPA Substance Registry System: 4-Phenyl-4-(trimethylsiloxy)butansaeure-methylester(106543-48-0)

Safety Data

• Hazardous Substances Data: 106543-48-0(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 100-52-7 benzaldehyde 
• 292638-85-8 acrylic acid methyl ester 
• 80737-53-7 c-2-Phenyl-t-2-(trimethylsiloxy)-r-1-cyclopropancarbonsaeure-methylester 
• 77903-44-7 t-2-Phenyl-c-2-(trimethylsiloxy)-r-1-cyclopropancarbonsaeure-methylester 

Downstream Products

• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 

Relevant articles and documents

Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams

The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.

Catalytic Hydrogenolysis of Methyl 2-Siloxycyclopropanecarboxylates: Investigations Regarding Chemoselectivity, Regioselectivity, and Stereoselectivity

Alkyl-substituted methyl 2-(trimethylsiloxy)cyclopropanecarboxylates 8a - 8f are opened by hydrogen in the presence of palladium on carbon affording 4-oxoalkanoic esters 10a - 10e by desilylation. 2-Phenyl-substituted cyclopropanes 8g - 8j, however, provide 4-phenylbutanoic esters 13g - 13j under these conditions.Formation of 13j is not stereoselective.Here the primary cyclopropane cleavage is followed by hydrogenolysis of the benzylic C-O bond.This subsequent reaction can be suppressed in the case of 8g by poisoning the catalyst with triethylamine; otherwise the tert-butyldimethylsiloxy compounds 11g - 11i have to be used.Butanoic esters 14h and 14i, respectively, are formed as mixtures of diastereomeres, which is another indication for nonstereoselective hydrogenolysis of cyclopropanes.Whereas slow desilylation by hydrogen was observed with the 3-phenyl-substituted cyclopropane derivative 8k, the vinylcyclopropane 8m in part suffers cleavage of the 1-3 bond of the three-membered ring.Regio- and stereoselectivity of the hydrogenolysis of the donor-acceptor-substituted cyclopropanes 8 and 11 are discussed.