53723-93-6

Usage

Uses

Used in Organic Synthesis:
TRIMETHYL-(2-PHENYL-CYCLOHEX-1-ENYLOXY)-SILANE is used as a reagent for the introduction of a trimethylsilyloxy group to organic molecules, enhancing the reactivity and properties of these molecules for various chemical reactions.
Used as a Protecting Group in Organic Chemistry:
In the field of organic chemistry, TRIMETHYL-(2-PHENYL-CYCLOHEX-1-ENYLOXY)-SILANE serves as a protecting group for alcohols and phenols, allowing chemists to perform selective reactions while preventing unwanted side reactions.
Used in the Production of Materials and Polymers:
TRIMETHYL-(2-PHENYL-CYCLOHEX-1-ENYLOXY)-SILANE is utilized in the manufacturing process of various materials and polymers due to its unique properties and reactivity, contributing to the development of new compounds with specific characteristics for different applications.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 1444-64-0 2-phenylcyclohexanol 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 591-50-4 iodobenzene 
• 5775-13-3 2-chloro-2-phenylcyclohexan-1-one 

Downstream Products

• 1444-65-1 (2S)-2-phenyl-1-cyclohexanone 
• 34281-93-1 (R)-2-phenylcyclohexanone 
• 4556-09-6 2-phenylcyclohex-2-enone 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 7079-07-4 2-allyl-2-phenylcyclohexan-1-one 
• 1328887-09-7 methyl 6-(hydroxyimino)-6-phenylhexanoate 
• 245123-77-7 Methanesulfonic acid (R)-2-oxo-1-phenyl-cyclohexylmethyl ester 
• 455331-14-3 (R)-2-Methyl-2-phenyl-cyclohexanol 
• 27855-09-0 (R)-(+)-2-methyl-2-phenylcyclohexanone 
• 245123-65-3 (R)-2-hydroxymethyl-2-phenylcyclohexanone 
• 55976-90-4 p-chloranil dianion 

Relevant academic research and scientific papers

Enantioselective Protonation of Silyl Enol Ethers Catalyzed by a Chiral Pentacarboxycyclopentadiene-Based Bronsted Acid

The enantioselective protonation of silyl enol ethers was realized in the presence of a pentacarboxycyclopenta-1,3-diene-based chiral Bronsted acid catalyst with water as an achiral proton source to give the corresponding α-aryl ketones in good yields and up to 75percent ee.

Method for the Direct Enantioselective Synthesis of Chiral Primary α-Amino Ketones by Catalytic α-Amination

A useful catalytic enantioselective approach has been developed for the synthesis of chiral ketamine analogs using Rh(II)-catalyzed amination of triisopropylsilyl enol ethers to form α-amino ketones with O-(4-nitrophenyl)hydroxylamine as nitrogen donor in 81-91% ee.

Chiral sulfinamide/achiral sulfonic acid cocatalyzed enantioselective protonation of enol silanes

The application of chiral sulfinamides and achiral sulfonic acids as a cocatalyst system for enantioselective protonation reactions is described. Structurally simple, easily accessible sulfinamides were found to induce moderate-to-high ee's in the formation of 2-aryl-substituted cycloalkanones from the corresponding trimethylsilyl enol ethers.

Chiral bronsted acid from a cationic gold(I) complex: Catalytic enantioselective protonation of silyl enol ethers of ketones

A chiral Bronsted acid has been developed from a cationic gold(I) disphosphine complex in the presence of alcoholic solvent and applied to the enantioselective protonation reaction of silyl enol ethers of ketones. Various optically active cyclic ketones were obtained in excellent yields and high enantioselectivities, including cyclic ketones bearing aliphatic substrates at the α-position. Furthermore, the application of this Bronsted acid was extended to the first Bronsted acid-catalyzed enantioselective protonation reaction of silyl enol ethers of acyclic substrates, regardless of their E/Z ratio.

Metal nitrite: A powerful oxidizing reagent

An efficient and simple source of nitroso reagents and their oxidation reactions are described. The combination of a Lewis acid and a metal nitrite was applied to the oxidation of silyl enol ethers. Amino acid and peptide derivatives were easily accessed through in situ C-C bond cleavage of fully substituted silyl enol ethers upon oxidation.

Development of a new Lewis base-tolerant chiral LBA and its application to catalytic asymmetric protonation reaction

A new Lewis base-tolerant LBA (Lewis Acid Assisted Bronsted Acid) derived from La(OTf)3 and (S)-HOP has been developed as a new chiral Bronsted acid. This acid has been successfully applied as a catalyst to asymmetric protonation reactions of silyl enol ethers of 2-substituted cyclic ketones.

A bronsted acid catalyst for the enantioselective protonation reaction

A highly reactive and robust chiral Bronsted acid catalyst, chiral N-triflyl thiophosphoramide, was developed. The first metal-free Bronsted acid catalyzed enantioselective protonation reaction of silyl enol ethers was demonstrated using this chiral Bronsted acid catalyst. The catalyst loading could be reduced to 0.05 mol % without any deleterious effect on the enantioselectivity. Copyright

Enantioselective protonation of silyl enol ethers and ketene disilyl acetals with Lewis acid-assisted chiral Bronsted acids: Reaction scope and mechanistic insights

Enantioselective protonation is a potent and efficient way to construct chiral carbons. Here we report details of the reaction using Lewis acid-assisted chiral Bronsted acids (chiral LBAs). The 1:1 coordinate complex of tin tetrachloride and optically active binaphthol ((R)- or (S)-BINOL) can directly protonate various silyl enol ethers and ketene disilyl acetals to give the corresponding α-aryl ketones and α-arylcarboxylic acids, respectively, with high enantiomeric excesses (up to 98% ee). A catalytic version of enantioselective protonation has also been achieved using stoichiometric amounts of 2,6-dimethylphenol and catalytic amounts of monomethyl ether of optically active BINOL in the presence of tin tetrachloride. This protonation is also effective for producing α-halocarbonyl compounds (up to 91% ee). DFT calculations on the B3LYP/LANL2DZ level show that the conformational structure of the chiral LBA and the orientation of activated proton on (R)-BINOLs are important for understanding the absolute stereochemistry of the products.