53282-55-6

Usage

Uses

Used in Organic Synthesis:
(CHMOTMS) is used as a reagent for the synthesis of various silicon-based materials and compounds. Its unique structure allows it to serve as a versatile building block in the creation of a wide range of products.
Used in Surface and Interface Modification:
(CHMOTMS) is used as a modifying agent in the alteration of surfaces and interfaces in different chemical processes and applications. Its ability to act as a hydrogen acceptor in catalytic hydrogenation reactions makes it a valuable component in these modifications.
Used in the Production of Polymers, Resins, and Coatings:
(CHMOTMS) is used as a key component in the manufacturing of silicon-containing polymers, resins, and coatings. Its cyclohexylidene functional group and trimethylsilyl groups contribute to the development of these materials with enhanced properties.
Used in Pharmaceutical and Chemical Industries:
(CHMOTMS) is used as a crucial intermediate in the development of new drugs and chemicals. Its unique properties make it a valuable asset in the synthesis of complex molecules and compounds within these industries.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 993-07-7 trimethylsilan 
• 201230-82-2 carbon monoxide 
• 110-83-8 cyclohexene 
• 622-45-7 cyclohexyl acetate 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 7449-74-3 N-methyl-N-trimethylsilylacetamide 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 100-49-2 cyclohexylmethyl alcohol 

Downstream Products

• 53282-32-9 cyclohexylidenemethyl trifluoromethanesulfonate 
• 95541-06-3 2,4-Dicyclohexyl-5-[2,2,3,3,3-pentafluoro-prop-(E)-ylidene]-[1,3]dioxolane 
• 95540-94-6 1-Cyclohexyl-4,4,5,5,5-pentafluoro-pent-2-yn-1-ol 
• 29517-58-6 1-allylcyclohexanecarbaldehyde 
• 127827-62-7 1-Formyl-1-(3-butenyl)cyclohexane 
• 57768-35-1 1-(phenylthio)-1-cyclohexanecarboxaldehyde 
• 181060-03-7 1-methylsulfanyl-cyclohexanecarboxaldehyde 
• 34177-18-9 spiro[4.4]nonan-2-one 
• 196598-95-5 4-(1-Hydroxymethyl-cyclohexyl)-butyric acid ethyl ester 
• 196598-97-7 4-(1-Iodomethyl-cyclohexyl)-butyric acid ethyl ester 
• 104750-38-1 (2RS,3SR)-2,6-dimethylphenyl 3-hydroxy-2-methyl-3-<1-(phenylthio)cyclohexyl>propionate 
• 104750-42-7 (3RS,4RS)-3-methyl-4-phenylthio-1-oxaspiro<4.5>decane 

Relevant academic research and scientific papers

Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark

The hydroperoxidation of alkyl enol ethers using N-hydroxyphthalimide and molecular oxygen occurred in the absence of catalyst, initiator, or light. The reaction proceeds through a radical mechanism that is initiated by N-hydroxyphthalimide-promoted autoxidation of the enol ether substrate. The resulting dioxetane products decompose in a chemiluminescent reaction that allows for photochemical activation of N-hydroxyphthalimide in the absence of other light sources.

One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable aldehydes yield β-hydroxy aldehydes in good yield. In a related reaction, the common laboratory solvent ethyl acetate functions as both an enolate precursor and a green reaction solvent. When thioesters are employed as enolate precursors, high yields for additions to non-enolizable aldehydes are routinely observed.

Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3-Metalate Rearrangement of Lithium Enolates

An unprecedented stereoselective synthesis of trisubstituted vinylboronates is reported to proceed by direct borylation of lithium ketone enolates under transition-metal-free conditions. The stereospecific C?O borylation of lithium enolates was triggered by a carbonyl-induced 1,3-metalate rearrangement via a C-bound boron enolate. DFT calculations and control experiments revealed that the stereoselectivity is controlled by sterics. A variety of stereospecific trisubstituted vinylboronates, together with several tetrasubstituted vinylboronates, were conveniently synthesized with the newly developed methodology. Based on the transformation of stereospecific vinylboronate, a single isomer of Dienestrol was efficiently obtained.

Silazanes/catalytic bases: Mild, powerful and chemoselective agents for the preparation of enol silyl ethers from ketones and aldehydes

We have developed an efficient method for the preparation of enol silyl ethers using novel agents, silazanes together with NaH or DBU catalyst, wherein TMS and TBDMS groups were smoothly and chemoselectively introduced into ketones and aldehydes under mil

Preparation of silyl enol ethers using (bistrimethylsilyl)acetamide in ionic liquids

(matrix presented) Ionic liquids have been used for the preparation of silyl enol ethers from aldehydes and ketones with (bistrimethylsilyl)acetamide (BSA) in good yields.

Scope and limitations of the [1,2]-alkylsulfanyl (SMe, SEt and SCH2Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans

Acid catalysed rearrangement of a series of 4-RS-1,3-diols (R = Me, Et, Bn and H) with toluene-p-sulfonic acid in dichloromethane gives stereospecifically substituted tetrahydrofurans via a [1,2]-SR shift in near quantitative yield. We comment on the structural variation of the migrating (RS) substituent and that of the migration origin and terminus on the outcome of the title reaction. We also report on the surprising similarity between an alkylsulfanyl (RS) and sulfanyl (SH) migrating group.

Facile synthesis of silyl enol ethers by Mg-promoted coupling of aliphatic carbonyl compounds with trimethylsilyl chloride

Treatment of aliphatic carbonyl compounds with trimethylsilyl chloride with Mg turning for Grignard reaction without any pre-treatment in N,N- dimethylformamide at room temperature brought about highly facile, effective and stereoselective coupling to give the corresponding silyl enol ethers in good yields.

Easy preparation of enoxysilanes from aldehydes and ketones catalyzed by samarium diiodide

Ketones and α-substituted aldehydes are converted to trimethylsilyl enol ethers by reaction with the trimethylsilyl ketene acetal of methyl isobutyrate in dichloromethane in presence of a catalytic amount of samarium diiodide.

Formation of quaternary centres via iron allyl cations. Rapid entry into spirocyclic ring systems

Ester-substituted allyltetracarbonyliron cations react with cycloalkylidene-type silyl enol ethers, silyl ketene acetals, and β-keto- esters to give 1,6-dicarbonyl compounds containing a newly formed quaternary centre. Selected condensation products are c

Efficient alkylsulfanyl (SMe, SEt and SCH2Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans

Treatment of a series of 4-RS-1,3-diols (R = Me, Et, Bn and H) with TsOH in CH2Cl2 gives substituted tetrahydrofurans. We discuss the scope of this reaction using structural variation of the migrating (RS) substituent. All reactions proceeded in high yield and give synthetically useful products.