1833-53-0

Usage

Uses

Used in Chemical Synthesis:
ISOPROPENYLOXYTRIMETHYLSILANE is used as a nucleophile for [Lewis acid-promoted C3-nucleophile substitution of tetracyclic bromide] because of its ability to participate in such reactions, making it a valuable component in chemical synthesis processes.
Used in Total Synthesis:
ISOPROPENYLOXYTRIMETHYLSILANE is used as a key component in the total synthesis of [±)-powelline] due to its involvement in the synthesis process, contributing to the creation of ISOPROPENYLOXYTRIMETHYLSILANE.
Used in Michael Addition Reactions:
ISOPROPENYLOXYTRIMETHYLSILANE is used as a reactant in dityltin bis(triflate) catalyzed Michael addition reactions of enol silyl ethers for [enhancing the reaction efficiency and selectivity] as it plays a crucial role in these specific types of reactions.
Used in Pharmaceutical Industry:
ISOPROPENYLOXYTRIMETHYLSILANE is used as an intermediate or reagent in the [pharmaceutical industry] for [the synthesis of various drugs and drug candidates], given its involvement in chemical reactions that can lead to the development of new pharmaceutical compounds.
Used in Research and Development:
ISOPROPENYLOXYTRIMETHYLSILANE is used as a research compound in [academic and industrial research] for [exploring new reaction pathways and understanding the reactivity of enol silyl ethers], as it provides valuable insights into the behavior of such compounds in various chemical reactions.

Purification Methods

Purify it by fractional distillation using a very efficient column at atmospheric pressure. It usually contains 5% of hexamethyldisiloxalane which boils at 99-101o, but is generally non-reactive and need not be removed. [Hauser & Hance J Am Chem Soc 71 5091 1952.] It has been distilled under N2 through a 15cm column packed with glass helices. Fraction b 99-104o is further purified by gas chromatography through a Carbowax column (Autoprep A 700) at a column temperature of 87o, and has a retention time of 9.5minutes. [Krüger & Rochow J Organomet Chem 1 476 1963-4.]

InChI:InChI=1/C6H14OSi/c1-6(2)7-8(3,4)5/h1H2,2-5H3

Upstream product

• 2295-12-7 1,1-dimethylsilacyclobutane 
• 67-64-1 acetone 
• 75-77-4 chloro-trimethyl-silane 
• 108-22-5 Isopropenyl acetate 
• 28483-52-5 tripropylstannyl-acetone 
• 5908-40-7 1-(trimethylsilyl)propan-2-one 
• 63698-90-8 C₁₅H₄₂N₃OPSi₄ 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 78-93-3 butanone 
• 17955-46-3 trimethylsilyltributyltin 
• 598-31-2 1-bromoacetone 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 1450-18-6 1,1,1-trimethyl-2,2,2-triphenyldisilane 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 

Downstream Products

• 583-05-1 1-phenylpentane-1,4-dione 
• 26205-43-6 O-trimethylsilylacetol 
• 53857-09-3 1,3-diphenyl-1,5-hexanedione 
• 36238-22-9 4-p-Tolyl-penten-⁽³⁾-on-⁽²⁾ 
• 109-09-1 2-chloropyridine 
• 6302-02-9 2-acetonylpyridine 
• 372-48-5 2-fluoropyridine 
• 108709-28-0 1-(2-Chloro-1-methyl-1-trimethylsilanyloxy-ethyl)-pyrrolidine-2,5-dione 
• 82319-13-9 1-chloro-2-{(trimethylsilyl)oxy}propene 
• 76634-95-2 3-chloro-2-(trimethylsilyloxy)prop-1-ene 
• 123-42-2 4-Hydroxy-4-methyl-2-pentanone 
• 132151-56-5 2-methoxy-1-p-tolylthiohept-2-en-6-one 
• 132151-54-3 1-p-tolylthioheptan-2,6-dione 
• 132151-57-6 4-vinyl-4-methoxy-5-p-tolylthiopentan-2-one 

Relevant academic research and scientific papers

VINYL COPPER DERIVATIVES 30. REACTIVITY OF γ-SILYLATED VINYL COPPER REAGENTS

γ-silylated vinyl copper reagents react with elecrtophiles with total retention of configuration of the C=C double bond.Oxidation, allylation, vinylation and acylation lead to functionalized dienes with a given geometry.

Tandem 1,4-addition reactions with benzene and alkylated benzenes promoted by pentaammineosmium(II)

Electrophiles such as dimethoxymethane and 3-penten-2-one react with the complex [Os(NH3)5-(η2-benzene)]2+ in the presence of triflic acid to form metastable benzenium intermediates. These benzenium intermediates further react with carbon nucleophiles including silyl ketene acetals, (silyloxy)alkenes, and phenyllithium in an overall tandem 1,4-addition sequence. The metal fragment controls the relative stereo- and regiochemistry for both electrophilic and nucleophilic addition steps. Upon oxidative demetalation with silver triflate, cis-1,4 cyclohexadienes are formed in yields ranging from 16 to 82%. This methodology can also be used to dearomatize toluene and ortho- and meta-xylene with unexpectedly high regio- and stereocontrol.

New C3v-symmetrical tribenzotriquinacenes bearing extended and oxy-functionalised alkyl groups at their benzhydrylic bridgeheads

A series of tribenzotriquinacene derivatives bearing three oxy-functionalised alkyl groups at the benzhydrylic bridgeheads (C-4b, C-8b and C-12b) have been synthesised. The 4b,8b,12b-triallyl derivative was used to generate the corresponding TBTQ-tris-acetaldehyde and TBTQ-tris(acetic acid), in which the functional groups stretch out from the convex rigid molecular surface. The corresponding tribromo derivate was found to undergo smooth Lewis acid-catalyzed C-C coupling with appropriate silyl enol ethers to afford a series of threefold 4b,8b,12b-(2-oxoalkyl)-substituted tribenzotriquinacenes. Six-fold nitration at the arene periphery was performed with 4b,8b,12b-tripropyltribenzotriquinacene and with the TBTQ-tris(acetic acid) to check for the effect of the bridgehead groupings as solubilising auxiliaries.

Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis

We report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P(V) species (i.e., fluorophosphorane) and a silyl enol ether, which allows for C-C bond formation between the polarity-mismatched sites. The bond formation that cannot be attained even by transition metal catalysis is accomplished by a P(III)/P(V) manifold.

Synthesis of Bridged Azacycles and Propellanes via Nitrene/Alkyne Cascades

A nitrene/alkyne cascade reaction terminating in C-H bond insertion to form functionalized bridged azacycles from carbonazidates is presented. Due to an initial Huisgen cyclization, all carbonazidates reacted with the alkyne in an exo mode in contrast to the use of sulfamate esters, which react predominately in an endo mode. Substrates with different ring sizes as well as different aryl and heteroaryl groups were also explored. Variation of the nitrene tether showed that 7-membered rings were the maximum ring size to be formed by nitrene attack on the alkyne. Examples incorporating stereocenters on the carbonazidate's tether induced diasteroselectivity in the formation of the bridged ring and two new stereocenters. Additionally, propellanes containing aminals, hemiaminals, and thioaminals formed from the bridged azacycles in the same reaction via an acid-promoted rearrangement.

Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

An enantioselective NHC (N-heterocyclic carbene) catalyzed synthesis of indenes from bifunctional α,β-unsaturated acyl fluorides and TMS enol ethers has been discovered. The reaction has broad generality (31 examples) and proceeds with high levels of enantioselectivity (most >92:8 er). Mechanistically the reaction likely occurs via a Michael/β-lactonization/decarboxylation sequence. Derivatization studies and limitations are discussed.

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.

Addition reaction of imidazoles and thiazoles with silyl enol ethers in the presence of alkyl chloroformate

Silyl enol ethers and ketene silyl acetals reacted with imidazole, thiazole, and their benzo derivatives in the presence of an alkyl chloroformate to give 2-substituted imidazolines and thiazolines in good yields via the intermediacy of unstable N-acylated quaternary salts of azoles. In addition, it was found that silyl enol ethers formed in situ were also useful for the reaction to afford the adducts only by simple sequential addition of five commercially available reagents. (C) 2000 Elsevier Science Ltd.

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.