84673-88-1

Usage

Uses

Used in Organic Synthesis:
(E)-3-bromo-1-(trimethylsilyl)propene is used as a reagent for the synthesis of various organic compounds, leveraging its reactivity and the presence of functional groups that facilitate numerous chemical reactions.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (E)-3-bromo-1-(trimethylsilyl)propene is used as a key intermediate in the development of new drugs, contributing to the creation of novel medicinal compounds with potential therapeutic applications.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical sector, (E)-3-bromo-1-(trimethylsilyl)propene serves as a vital component in the synthesis of chemicals used in agriculture, such as pesticides and fertilizers, to enhance crop protection and yield.
Used in the Preparation of Functionalized Silanes:
(E)-3-bromo-1-(trimethylsilyl)propene is also utilized in the preparation of functionalized silanes, which are important in various industrial applications, including materials science and surface modification.
Used as a Protective Group in Organic Chemistry:
In organic chemistry reactions, (E)-3-bromo-1-(trimethylsilyl)propene acts as a protective group for alcohols and amines, preventing unwanted side reactions and ensuring the selective formation of desired products.
Overall, (E)-3-bromo-1-(trimethylsilyl)propene is a valuable compound in the fields of research and industry, with applications spanning across pharmaceuticals, agrochemicals, materials science, and more, due to its unique reactivity and functional group versatility.

Upstream product

• 5272-36-6 3-trimethylsilyl-2-propyn-1-ol 
• 558-13-4 carbon tetrabromide 
• 59376-64-6 (2E)-3-(trimethylsilyl)prop-2-en-1-ol 

Downstream Products

• 105897-64-1 1-(tert-Butyl-dimethyl-silanyl)-5-ethoxy-3-phenylsulfanyl-3-((E)-3-trimethylsilanyl-allyl)-pyrrolidin-2-one 
• 155219-88-8 1-benzyl-1-<(E)-3-(trimethylsilyl)-2-propenyl>-2-hydrazinecarboxylic acid allyl ester 
• 89002-98-2 (E)-3-trimethylsilylprop-2-enyl p-tolyl sulphone 

Relevant academic research and scientific papers

ENANTIOSELECTIVE SYNTHESIS OF THE NAGILACTONE RING SYSTEM VIA VINYLSILANE-MEDIATED POLYENE CYCLIZATION.

The functionalized tricyclic nagilactone precursor 19 was synthesized by a route featuring a vinylsilane terminated/1,3-dioxane acetal initiated bicyclization.Relative and absolute stereochemical control were achieved via the optically active pentenolide template 14.

An Aliphatic Bischler-Napieralski Reaction: Dihydropyridones by Cyclocarbonylation of 3-Allylimidazolidin-4-ones

The N-chloroformylimidazolidinone derivative of enantiopure l-alanine was deprotonated to form an enolate and functionalized with a series of allylic halides. Treatment of the resulting carbamoyl chlorides with potassium iodide led to cyclization of the allylic substituent onto the carbonyl group in an intramolecular aliphatic Friedel-Crafts-type acylation that corresponds to an aliphatic Bischler-Napieralski reaction. The product 3,4-dihydropyridinones were amenable to further functionalization, and finally hydrolysis, to deliver a series of enantio-enriched pipecolic acid derivatives.

Expedient access to branched allylic silanes by copper-catalysed allylic substitution of linear allylic halides

An unprecedented copper-catalysed allylic transposition enables the regioselective synthesis of branched allylic silanes from linear allylic halides through direct C-Si bond formation.

Preparation of enantiomerically pure 9-azabicyclo[3,3,1]nonene derivatives. Stereochemical requirements of vinyl- and allylsilanes in iminium ion initiated cyclization

Asymmetric synthesis of the 9-azabicyclo[3,3,1]nonene skeleton of granatanine has been achieved through the cyclization of non-racemic (Z)-vinylsilane oxazolidine (Z)-2, an iminium ion precursor. The corresponding (E)-isomer (E)-2 did not cyclize in the s

A convenient and stereoselective synthesis of trimethylsilylvinyl oxiranes via silylated telluronium allylide+

Trimethylsilylated diisobutyltelluronium allylide, a moderately stabilized telluronium ylide, generated from 3-trimethylsilyl-2-propenyldiisobutyltelluronium bromide (3) with LiTMP, reacted with carbonyl compounds to afford trimethylsilylvinyl oxiranes in excellent yields with high syn stereoselectivity.

Wittig Rearrangement-Peterson Olefination Sequence: A Stereocontrolled Entry to Terminal Conjugated Trienes

A new and highly stereocontrolled entry to terminal conjugated trienes is described which relies upon the diastereoselective Wittig rearrangement of γ-(silyl)allylic propargyl ethers followed by Peterson olefination.The synthetic utility of this meth

REGIOSELECTIVE SYNTHESIS OF (+/-)-GABACULINE

(+/-)-Gabaculine has been synthesized via an intramolecular reaction of an N-acyliminium intermediate with a propargyl silane, followed by allene ozonolysis and a Shapiro reaction.

Silylalkenes and -dienes via (Silylalkylidene)phosphoranes

The reaction of the (silylalkylidene)phosphoranes 3 and 4 with the ketones 5 - 7 and 16 leads to the silylated olefins 8 - 10 and 17, 18.With fluorenone (11), 3 affords the spiro compound 14, via (silylpropylidene)fluorene 13, which is also obtained by dehydration of 9--9-fluorenol (12).With the ketones 5 - 7 and 11, triphenylphosphorane (20) yields the silylated dienes 21 - 24.From cyclohexane (22) and tetracyanoethene (25) the spiran 26 is formed by cycloaddition.