66324-10-5

Basic information

• Product Name: Silane, (1,1-dimethylethyl)dimethyl[(1-phenylethenyl)oxy]-
• CAS NO: 66324-10-5
• Molecular Formula: C14H22OSi
• Molecular Weight: 234.414
• Mol File: 66324-10-5.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: Silane, (1,1-dimethylethyl)dimethyl[(1-phenylethenyl)oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, (1,1-dimethylethyl)dimethyl[(1-phenylethenyl)oxy]-(66324-10-5)
• EPA Substance Registry System: Silane, (1,1-dimethylethyl)dimethyl[(1-phenylethenyl)oxy]-(66324-10-5)

Safety Data

• Hazardous Substances Data: 66324-10-5(Hazardous Substances Data)

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 98-86-2 acetophenone 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 213339-57-2 C₈H₁₅F₆NO₄S₂Si 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 2142-69-0 2-bromophenyl methyl ketone 
• 1312716-87-2 2-(2-bromophenyl)-2-((tert-butyldimethylsilyl)oxy)propanenitrile 
• 1312716-70-3 2-(2-bromophenyl)-2-tert-butyl(dimethylsilyl)oxypropanal 
• 29681-57-0 tert-butyldimethylsilane 
• 75732-41-1 tert-butyldimethylsilyl benzoate 

Downstream Products

• 89318-28-5 4-[(E)-2-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-vinyl]-4H-pyridine-1-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 105618-98-2 1-(ethoxycarbonyl)-3-(methoxycarbonyl)-4-(2-oxo-2-pheneylethyl)-1,4-dihydropyridine 
• 90720-42-6 4-ethyl-1-phenylhexane-1,3-dione 
• 90720-27-7 3-(tert-Butyl-dimethyl-silanyloxy)-2,2-diethyl-3-phenyl-cyclobutanone 
• 90720-36-8 3-(tert-Butyl-dimethyl-silanyloxy)-4-ethyl-1-phenyl-hex-3-en-1-one 
• 6263-83-8 1,5-diphenyl-1,5-pentanedione 
• 122124-63-4 3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-1-phenyl-5-trimethylsilanyl-pent-4-yn-1-one 
• 105590-54-3 (R)-4-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3,3-dimethyl-1-phenyl-hexane-1,5-dione 
• 105590-57-6 (S)-4-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-1-phenyl-hexane-1,5-dione 
• 105590-57-6 (R)-4-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-1-phenyl-hexane-1,5-dione 
• 105590-56-5 (S)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-hexyl]-3,3-dimethyl-1-phenyl-hexane-1,5-dione 
• 105590-60-1 (3S,4S)-4-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-hexyl]-1,3-diphenyl-hexane-1,5-dione 
• 105590-60-1 (3S,4R)-4-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-hexyl]-1,3-diphenyl-hexane-1,5-dione 
• 122124-55-4 3-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-1,5-diphenyl-pent-4-yn-1-one 

Relevant articles and documents

Nucleophilic Attack on Nitrogen in Tetrazines by Silyl-Enol Ethers

The nucleophilic addition of silyl-enol ethers to nitrogen in 3-monosubstituted s-tetrazines mediated by BF3 is reported. The preference for this azaphilic addition over the usually observed inverse electron demand Diels-Alder reactions was evaluated theoretically and corroborated by experiments. The substrate dependency of this unusual reaction was rationalized by determination of the activation barriers and on the basis of the activation strain model by employing density functional theory.

Photocatalytic Vicinal Aminopyridylation of Methyl Ketones by a Double Umpolung Strategy

A photocatalytic double umpolung strategy for the vicinal aminopyridylation of ketones was developed using pyridinium N?N ylides. The inversion of the polarity of the pyridinium N?N ylides by single-electron oxidation successfully enables radical-mediated 1,3-dipolar cycloadditions with enolsilanes formed in situ from ketones, followed by homolytic cleavage of the N?N bond. Intriguingly, the nucleophilic amino and electrophilic pyridyl groups in the ylides can be installed at the nucleophilic α-position and electrophilic carbonyl carbon, respectively, which are typically inaccessible by their innate polarity-driven reactivity. This method accommodates a broad scope, and the utility was further demonstrated by the late-stage functionalization of complex biorelevant molecules. Moreover, the strategy can be successfully applied to enamides.

FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers

Herein we report the first catalytic transfer hydrogenation of silyl enol ethers. This metal free approach employs tris(pentafluorophenyl)borane and 2,2,6,6-tetramethylpiperidine (TMP) as a commercially available FLP catalyst system and naturally occurring γ-terpinene as a dihydrogen surrogate. A variety of silyl enol ethers undergo efficient hydrogenation, with the reduced products isolated in excellent yields (29 examples, 82 % average yield).