6651-34-9

Usage

Uses

Used in Organic Synthesis:
2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE is used as a nucleophile in Lewis Acid-Catalyzed reactions for its ability to participate in the formation of new chemical bonds under the influence of a Lewis acid catalyst. This application is particularly valuable in the synthesis of complex organic molecules where selective bond formation is required.
Used in Pharmaceutical and Biochemical Research:
In the field of pharmaceutical and biochemical research, 2-METHYL-1-(TRIMETHYLSILOXY)-1-PROPENE may be used as a reagent in the direct conversion of α-amino acids into β-amino aldehydes. This transformation is significant as it allows for the synthesis of biologically active compounds and intermediates that are otherwise challenging to obtain, facilitating the development of new drugs and therapeutic agents.

InChI:InChI=1/C7H16OSi/c1-7(2)6-8-9(3,4)5/h6H,1-5H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 56640-70-1 2-methylprop-1-en-1-ol 
• 18881-60-2 bis-trimethylsilanyl-acetonitrile 
• 78-84-2 isobutyraldehyde 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 15693-82-0 (trimethylsilyl)cobalt tetracarbonyl 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 

Downstream Products

• 54322-96-2 (+/-)-3-Hydroxy-2,2-dimethyl-5-phenylvaleraldehyde 
• 54322-95-1 3-Hydroxy-2,2-dimethyl-4-phenyl-butyraldehyde 
• 55638-19-2 3-Chloro-benzoic acid 2-hydroxy-2-methyl-1-trimethylsilanyloxy-propyl ester 
• 142916-45-8 1-(2,2-dimethyl-3-oxopropyl)perhydro-2-azepinone 
• 20967-51-5 3-(phenylthio)-2,2-dimethylpropanal 
• 128672-54-8 2,2-dimethyl-3-methoxy-4-p-chlorophenylthiopent-4-enal 
• 128672-58-2 E-2,2-dimethyl-5-methoxy-4-p-chlorophenylthiopent-4-enal 
• 128672-57-1 Z-2,2-dimethyl-5-methoxy-4-p-chlorophenylthiopent-4-enal 
• 56421-90-0 2-(4-chlorophenylthio)-2-methylpropanal 
• 78824-92-7 2-Methyl-2-(5-oxo-cyclohex-3-enyl)-propionaldehyde 
• 78824-93-8 5-(2,2-Dimethoxy-1,1-dimethyl-ethyl)-cyclohex-2-enone 
• 31758-87-9 1-(4-chlorophenyl)-2,2-dimethylpropane-1,3-diol 
• 56010-54-9 2,2-dimethyl-1-(4-nitrophenyl)-1,3-propanediol 
• 105449-77-2 2-benzylsulfanyl-2-methylpropanal 

Relevant academic research and scientific papers

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.

Sc(OTf)3-catalyzed smooth tandem [3+2] cycloaddition/ring opening of donor-acceptor cyclopropane 1,1-diesters with enol silyl ethers

Catalyzed by Lewis acids, donor-acceptor cyclopropane 1,1-diesters reacted with enol silyl ethers to afford 1,6-dicarbonyl compounds in moderate to excellent yields. This supplied a mild carbon-carbon bond-forming method from the ring opening of cyclopropanes. A smooth tandem [3+2] cycloaddition/ring opening process has been clearly proved by an independent experiment.

Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan

By the synergistic catalysis of samarium ion and mercaptan, a series of 5-oxoalkanals was converted to (substituted) δ-lactones in efficient and stereoselective manners. This one-pot procedure comprises a sequence of acetalization, Tishchenko reaction and lactonization. The deliberative use of mercaptan, by comparison with alcohol, is advantageous to facilitate the catalytic cycle. The reaction mechanism and stereochemistry are proposed and supported by some experimental evidence. Such samarium ion/mercaptan cocatalyzed reactions show the feature of remote control, which is applicable to the asymmetric synthesis of optically active δ-lactones. This study also demonstrates the synthesis of two insect pheromones, (2S,5R)-2-methylhexanolide and (R)-hexadecanolide, as examples of a new protocol for asymmetric reduction of long-chain aliphatic ketones.

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.

A practical method for the preparation of trimethylsilyl enol ethers

In the mixed system of chlorotrimethylsilane/triethyl amine/N,N-dimethylformamide/potassium iodide/petroleum ether, aldehydes or ketones are silylated to silyl enol ethers at room temperature. The N,N-dimethylformamide/potassium iodide layer can be used as circulating liquor for many times. The yields are high.

A Simple and Highly Diastereoselective One-Pot Synthesis of Mannich-Bases

A convenient one-pot procedure for the synthesis of β-amino ketones 5 from economical shelf reagents is described. Iminium salts 3 are generated in virtually quantitative yields from secondary amines 1 and aldehydes 2 mediated by NaI/Me3SiCl/NEt3. Subsequently, the salts 3 are used for the in situ aminoalkylation of enamines 4. The method provides the Mannich bases 5 in high yields and excellent diastereoselectivities (>96 % ds). It can also be applied for the aminoalkylation of other nucleophiles such as imines or electron-rich aromatic compounds.

A New Version of the Peterson Olefination Using Bis(trimethylsilyl)methyl Derivatives and Fluoride Ion as Catalyst

Reaction between a variety of bis(trimethylsilyl)methyl derivatives and carbonyl compounds under fluoride ion as catalyst is described.The reaction works especially well with nonenolizable carbonyl compounds to give the expected alkenes in high yields and, in some cases, with high stereoselectivity.Application of this methodology to an intramolecular alkenation providing a tricyclic benzocarbacephem ring system is also described.

The mechanism of the formation of silyl enol ethers from hydrosilanes and organic carbonyl compounds in the presence of cobalt carbonyls. Kinetic investigation of some reaction steps

The cleavage of isobutyrylcobalt tetracarbonyl with triethylsilane gives (triethylsilyl)cobalt tetracarbonyl, isobutyraldehyde, dicobalt octacarbonyl, and the corresponding unsaturated and saturated silyl ethers. Silyl enol ether was also formed, along wi

A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS. PART.I. FROM SIMPLE ALDEHYDES AND KETONES.

A new, practical route to enoxysilanes is described from simple enolizable aldehydes or ketones, using the trimethylchlorosilane-sodium iodide-tertiary amine reagent in acetonitrile.From certain aldehydes, an onium intermediate has been isolated.A conformational study of this onium intermediate and a thermal unimolecular syn-elimination process may explain the stereoselectivity of the reaction.Such an interpretation can be extended to all the aldehydes and ketones considered.Steric factors related to the nature both of the cabonyl derivative and of the amine play a capital role for the regio- as well as for the stereo-control of the reaction.