115579-47-0

Usage

Functional Groups

Allyl group ( \textC3\textH5 ): Provides the potential for addition reactions.
Dimethylamino group ( \textC2\textH5\textN ): Offers basic properties and can participate in substitution reactions.

Application

Organic Synthesis: Used as a reagent or catalyst in various organic reactions.
Production of Organosilicon Compounds: Serves as a precursor for the synthesis of organosilicon compounds.

Reactivity

Addition Reactions: Due to the presence of the allyl group.
Substitution Reactions: Enabled by the dimethylamino group.

Versatility

Exhibits diverse applications in the chemical industry.

Synthetic Utility

Functions as a valuable building block for synthesizing complex organic molecules.

InChI:InChI=1/C9H21NSi/c1-6-9-11(4,5)10(7-2)8-3/h6H,1,7-9H2,2-5H3

Upstream product

• 6026-02-4 (N,N-diethylamino)dimethylchlorosilane 
• 2622-05-1 allylmagnesium bromide 
• 816-43-3 lithium diethylamide 
• 75-78-5 dimethylsilicon dichloride 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 1515-78-2 buta-1,3-dien-1-ylbenzene 
• 119135-31-8 (E)-1-phenyl-4-isopropoxydimethylsilyl-3-buten-1-ol O-trimethylsilyl ether 
• 25203-83-2 (E)/(Z)-buta-1,3-dien-1-ylcyclohexane 
• 119093-07-1 (E)-1-cyclohexyl-4-isopropoxydimethylsilyl-3-buten-1-ol O-trimethylsilyl ether 
• 613243-03-1 3-[dimethyl((E)-3'-trimethylsilanyl-prop-1'-enyl)silanyloxy]-3-phenylpropanal 
• 613243-02-0 ethyl 3-[dimethyl((E)-3'-trimethylsilanyl-prop-1'-enyl)silanyloxy]-3-phenylpropanoate 

Relevant academic research and scientific papers

Temporary silicon connection strategies in intramolecular allylation of aldehydes with allylsilanes

(Chemical Equation Presented) Three γ-(amino)silyl-substituted allylsilanes 14a-c have been prepared in three steps from the corresponding dialkyldichlorosilane. The aminosilyl group has been used to link this allylsilane nucleophile to a series of β-hydroxy aldehydes through a silyl ether temporary connection. The size of the alkyl substituents at the silyl ether tether governs the outcome of the reaction on exposure to acid. Thus, treatment of aldehyde (E)-9aa, which contains a dimethylsilyl ether connection between the aldehyde and allylsilane, with a range of Lewis and Bronsted acid activators provides an (E)-diene product. The mechanism of formation of this undesired product is discussed. Systems containing a sterically more bulky diethylsilyl ether connection react differently: thus in the presence of TMSOTf and a Bronsted acid scavenger, intramolecular allylation proceeds smoothly to provide two out of the possible four diastereoisomeric oxasilacycles, 23 (major) and 21 (minor). A diene product again accounts for the remaining mass balance in the reaction. This side product can be completely suppressed by using a sterically even more bulky diisopropylsilyl ether connection in the cyclization precursor, although this is now at the expense of a slight erosion in the 1,3-stereoinduction in the allylation products. The sense of 1,3-stereoinduction observed in these intramolecular allylations has been rationalized by using an electrostatic argument, which can also explain the stereochemical outcome of a number of related reactions. Levels of 1,4-stereoinduction in the intramolecular allylation are more modest but can be significantly improved in some cases by using a tethered (Z)-allylsilane in place of its (E)-stereoisomer. Oxidation of the major diastereoisomeric allylation product 23 under Tamao-Kumada conditions provides an entry into stereodefined 1,2-anti-2,4-syn triols 28.

Using a Temporary Silicon Connection in Stereoselective Allylation with Allylsilanes: Application to the Synthesis of Stereodefined 1,2,4-Triols

(Equation presented) Treatment of aldehyde 6 with TMSOTf, in the presence of a Bronsted acid scavenger, effects an intramolecular allylation to provide the oxasilacycle 7 as the major diastereoisomer. Tamao oxidation of the C-Si bond in 7 affords the corresponding 1,2,4-triol 9.