6213-94-1

Usage

InChI:InChI=1/C5H12OSi/c1-5-6-7(2,3)4/h5H,1H2,2-4H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 78-78-4 methylbutane 
• 4387-13-7 bis(formylmethyl)mercury 
• 109-99-9 tetrahydrofuran 
• 108-05-4 vinyl acetate 
• 43016-96-2 2-Bromo-2-trimethylsilanyl-ethanol 
• 75-07-0 acetaldehyde 
• 1471-04-1 allyl tert-butyl ether 
• 3739-64-8 allyl n-butyl ether 
• 592-72-3 allyl 3-methylbutyl ether 
• 124471-48-3 allyl 1-ethylpropyl ether 
• 82473-55-0 allyl nonyl ether 
• 5796-98-5 bis-trimethylsilanyl peroxide 
• 917-57-7 vinyllithium 

Downstream Products

• 60584-64-7 1,1,3,5,7,7-hexaethoxy-heptane 
• 1497-49-0 glutacondianil hydrochloride 
• 102525-97-3 3,5,7,7-tetraethoxy-1-heptanal 
• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 5314-42-1 acetaldehyde dicyclohexyl acetal 
• 871-22-7 dibutyl acetal 
• 1825-65-6 butoxytrimethylsilane 
• 17877-28-0 acetaldehyde butyl trimethylsilyl acetal 
• 107-46-0 Hexamethyldisiloxane 
• 75271-39-5 trimethyl(1-phenoxyethoxy)silane 
• 693-38-9 vinyl palmitate 
• 42409-05-2 vinyl nonafluorobutane-1-sulfonate 

Relevant academic research and scientific papers

CONVERSION OF SOME ALKENYLTRIMETHYLSILANES INTO SILYL ENOL ETHERS

The cycloaddition products (5-trimethylsilylisoxazolines) between alkenyltrimethylsilanes and acetonitrile oxide undergo thermolytic rearrangement-cycloreversion to afford silyl enol ethers of retained stereochemistry vs. the starting alkenylsilanes.

Novel synthesis routes for the preparation of low toxic vinyl ester and vinyl carbonate monomers

UV curing of photopolymerizable monomers, like (meth)acrylates, has been utilized for coatings for more than half a century and more recently in further developed areas such as tissue engineering. However, these monomers have major disadvantages, e.g., high irritancy and cytotoxicity, which leads to limited use in tissue engineering regarding health issues. Vinyl esters (VE) and vinyl carbonates (VC) can compete with (meth)acrylates in terms of material properties and have significantly lower toxicity, but lack in cost efficient synthesis methods. The purpose of this communication is to establish new pathways to overcome this drawback. It was shown that VEs can be synthesized either by vinyloxy trimethylsilane or by acetaldehyde in excellent yields. Moreover, a new method to synthesize vinyl chloroformate as precursor for VCs in lab scale was evolved by a catalyzed reaction of vinyloxy trimethylsilane with a phosgene solution. Finally, the cytotoxicity tests showed auspicious results.

Efficient room-temperature O-silylation of alcohols using a SBA-15-supported cobalt(II) nanocatalyst

The O-silylation of OH groups of alcohols and phenols with hexamethyldisilazane (HMDS) was achieved in high-to-excellent yields using catalytic quantities of a SBA-15-supported cobalt(II) nanocatalyst (typically 0.5 mol-%) at room temperature and under solvent-free conditions. Furthermore, the heterogeneous catalyst showed an excellent durability and can be conveniently reused by filtration for at least twelve times without any noticeable loss of activity. Copyright

Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes

Chiral phosphoramide catalyzed-enantioselective aldol addition of an acetaldehyde-derived trialkylsilyl enol ether to aromatic aldehydes provides protected aldol products in good yields with good to excellent enantioselectivities. Preliminary studies show that the aldolization intermediate (a chlorohydrin adduct) can be trapped with tert-butyl isocyanide to form an α-hydroxy lactone with good selectivity in a singlepot operation.

Synthesis of vinyl carbonates for use in producing vinyl carbamates

A method for making a vinyl carbonate represented by the formula (I): CH2═CHOC(O)X1R1??(I) wherein X1is oxygen or sulfur and R1is a substituted or an unsubstituted aliphatic alkyl, aryl, aryl alkyl, olefinic, vinyl, or cycloaliphatic group comprises: (a) reacting a compound represented by the formula (II): X2C(O)X1R1??(II) ?wherein X2is a halogen other than fluorine, with a compound represented by the formula (III): M1—F??(III) ?wherein M1is selected from a Group IA metal, in the presence of a first phase transfer catalyst and a first organic solvent, to form a compound represented by the formula (IV): FC(O)X1R1??(IV) and (b) reacting a compound represented by the formula (IV) with a compound represented by the formula (V): CH2═CHOSi(R2)3??(V) ?wherein R2is a substituted or an unsubstituted aliphatic alkyl, aryl, aryl alkyl olefinic, vinyl, or cycloaliphatic group, or any combination thereof, in the presence of a metal salt represented by the formula M2—F wherein M2is a Group IA metal, a second phase transfer catalyst, and a second organic solvent, to form the compound represented by formula (I).

Synthesis of vinyl carbonates for use in producing vinyl carbamates

A method for making a vinyl carbonate represented by the formula (I): CH2═CHOC(O)X1R1??(I) wherein X1is oxygen or sulfur and R1is a substituted or an unsubstituted aliphatic alkyl, aryl, aryl alkyl, olefinic, vinyl, or cycloaliphatic group comprises: (a) reacting a compound represented by the formula (II): X2C(O)X1R1??(II) wherein X2is a halogen other than fluorine, with a compound represented by the formula (III): M1—F??(III) wherein M1is selected from a Group IA metal, in the presence of a first phase transfer catalyst and a first organic solvent, to form a compound represented by the formula (IV): FC(O)X1R1??(IV); ?and (b) reacting a compound represented by the formula (IV) with a compound represented by the formula (V): CH2═CHOSi(R2)3??(V) wherein R2is a substituted or an unsubstituted aliphatic alkyl, aryl, aryl alkyl olefinic, vinyl, or cycloaliphatic group, or any combination thereof, in the presence of a metal salt represented by the formula M2—F wherein M2is a Group IA metal, a second phase transfer catalyst, and a second organic solvent, to form the compound represented by formula (I).

Mechanism-based inactivation of α-chymotrypsin

The peptidyl ester derivatives of 2,2-dichlorocyclopropanol and the amide derivative of 2,2-dichlorocyclopropylamine were prepared as novel mechanism-based inactivators of α-chymotrypsin. The esters inactivated α-chymotrypsin irreversibly but the amide did not show any irreversible inhibitory activity toward α-chymotrypsin.

A Novel Synthetic Route to 2-Halo-3,4-Dicyanopyridines

2-Bromo-3,4-dicyanopyridine 2 was obtained in moderate yield by reacting 1,1,2,2-tetracyano-3-trimethylsiloxycyclobutane 1 with phosphorus tribromide.Similarly, reaction of 1 with chlorinating reagents such as thionyl chloride and oxalyl chloride led to the corresponding 2-chloro-3,4-dicyanopyridine 3 in 40 percent yield.A reaction mechanism is suggested.

THE WITTIG REARRANGEMENT AS A PRACTICAL METHOD FOR ALDEHYDE SYNTHESIS

If the rearrangement of metalated allyl ethers 2 (or 4) is accomplished in the presence of potassium tert-butoxide, primary alkyl groups preferentially migrate to the unsubstituted allylic terminus (γ-position).Enolates 7 and 1-vinylalcoholates 6 (by alkyl migration to the α-position, adjacent to the oxygen atom) are produced in an approximate ratio of 9 : 1.Because of the endo-configuration of their organometallic precursors, the enolates exclusively emerge in the (Z)-configuration as shown by trapping with chlorotrimethylsilane and isolation of the resulting O-silyl (Z)-enethers.Hydrolysis of the latter affords the corresponding aldehydes with good yields. -The rearrangement is mechanistically still obscure.A concerted process as the main reaction mode is unlikely.The intermediacy of zwitterionic metallomers 18 and solvent caged radical pairs 17 is tentatively suggested.

Synthesis of Trimethylsilyloxy and Hydroxy Compounds from Carbanions and Bis(trimethylsilyl)peroxide.

The reactions of bis(trimethylsilyl)peroxide with alkyl, vinyl, alkynyl, aromatic and heteroaromatic anions are described.Depending on the reaction conditions, the trimethylsilyloxy derivatives can be obtained alone or together with the corresponding trimethylsilyl derivatives, which is sometimes the major product.Enolates, generated using magnesium diisopropylamide give the corresponding hydroxycarbonyl compounds in good yields.An attempt to rationalise the above results is given, emphasising the wide use of bis(trimethylsilyl)peroxide in organic synthesis as an electrophilic hydroxylation reagent.