43209-86-5

Usage

Uses

Used in Organic Chemistry:
3-Trimethylsilyl-3-buten-2-one is used as a Michael acceptor for annulation reactions, which are important in the synthesis of complex organic molecules and the formation of cyclic structures. Its reactivity allows for the creation of γ,δ-unsaturated ketones, which are key intermediates in the synthesis of various organic compounds.
Used in Synthesis of Dienes:
3-Trimethylsilyl-3-buten-2-one is also utilized as a precursor to a stabilized Diels-Alder diene, which is crucial in the Diels-Alder reaction, a fundamental [4+2] cycloaddition process in organic chemistry. This reaction is widely used to form six-membered rings in organic molecules, contributing to the synthesis of a wide range of natural products and pharmaceuticals.
Used in the Formation of Diene Adducts:
3-Trimethylsilyl-3-buten-2-one is employed in the formation of diene adducts, which are essential in the development of complex organic structures and have applications in various chemical industries.
Physical properties:
3-Trimethylsilyl-3-buten-2-one has a boiling point of 72 °C at a pressure of 50 mmHg, which is an important consideration when handling and utilizing 3-Trimethylsilyl-3-buten-2-one in various chemical processes.

Preparation

3-Trimethylsilyl-3-buten-2-one is prepared by the reaction of (1-bromovinyl) trimethylsilane with acetaldehyde. An alternative synthesis from acrolein has been published.

Upstream product

• 66374-47-8 3-trimethylsilanyl-but-3-en-2-ol 
• 87241-31-4 Me₃SnC(SiMe₃)CH₂ 
• 75-36-5 acetyl chloride 
• 10111-13-4 (E/Z)-1-methyl-1-propenyltrimethylsilane 
• 49750-22-3 1-(trimethylsilyl)vinylmagnesium bromide 
• 108-24-7 acetic anhydride 
• 13683-41-5 1-bromo-1-(trimethylsilyl)ethene 
• 69519-67-1 2-trimethylsilyl-3,3-diethoxypropene 
• 58107-33-8 2-(trimethylsilyl)acrylaldehyde 

Downstream Products

• 93913-62-3 3(R)-methyl-6(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>-2(S)-(3-oxobutyl)cyclohexanone 
• 2158-59-0 cryptone 
• 109001-58-3 Methyl 4,6-O-Benzylidene-3-deoxy-3-C-methyl-3,2-C-(3'-oxobutan-1'-yl-4'-ylidene)-α-D-arabino-hexopyranoside 
• 135056-64-3 (4aS,4bS,6R,8aR,10S,10aS)-10-Methoxy-2,4a-dimethyl-6-phenyl-3-trimethylsilanyl-4a,4b,8,8a-tetrahydro-4H-1,5,7,9-tetraoxa-phenanthren-10a-ol 
• 143008-67-7 2,4-dimethyl-3-(3-methyl-3-butenyl)cyclohexan-1-one 
• 143008-68-8 (4aRS,5SR,6RS)-4,4a,5,6,7,8-hexahydro-4a,6-dimethyl-5-(3-methyl-3-butenyl)-2(3H)-naphthalenone 
• 143008-66-6 (4aRS,5SR,6RS)-4,4a,5,6,7,8-hexahydro-2,4a,6-trimethyl-5-(3-methyl-3-butenyl)-3-(trimethylsilyl)-8aH-1-benzopyran-8a-ol 
• 101630-50-6 3--2-cyclohexen-1-on 
• 166317-80-2 (1R,2S,4S,8R)-2-(3'-oxobutyl)-9-<(triisopropylsilyl)oxy>-p-menthone 
• 1026246-65-0 (2R,3R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethyl-2-(3-oxo-2-trimethylsilanyl-butyl)-cyclohexanone 
• 99423-48-0 ethyl 2-oxo-3-(3-oxobutyl)-1-cyclohexanecarboxylate 
• 262352-81-8 (1S,2R,4R)-1-Methyl-2-(3-oxobutyl)-3-oxo-4-(1-methylethyl)cyclohexane 
• 4071-57-2 2-Methyl-6-(3-oxobutyl)cyclohexanone 
• 22472-36-2 2,3-bis(trimethylsilyl)-buta-1,3-diene 

Relevant academic research and scientific papers

Epoxidation versus Allylic Oxidation (CH Insertion) in the Oxyfunctionalization of Vinylsilanes and β-Hydroxy Derivatives by Dimethyldioxirane

Epoxidation of acyclic vinylsilanes by dimethyldioxirane affords α,β-epoxysilanes in high yields, whereas for cyclic vinylsilanes appreciable amounts of allylic oxidation is observed.These competitive pathways become more pronounced, when the reactivity of the double bond is decreased by electronic and/or steric factors.

Highly Regio- and Diastereoselective One-Pot Synthesis of Silyl Epoxy Alcohols and Vinylsilanes by Direct Hydroxy-Epoxidation

A direct synthesis of silyl epoxy alcohols from vinylsilanes is described.It consists of the regioselective ene reaction of the vinylsilanes with singlet oxygen, which proceeds with predominant hydrogen abstraction at the position geminal to the silyl group.The resulting silyl allylic hydroperoxides were treated, without isolation, subsequently with Ti(O-i-Pr)4 to afford the silyl epoxy alcohols in good yields and very high diastereomeric ratios, which ranged from 93:7 to greater than 97:3.Alternatively, the vinylsilanes were photooxygenated directly in the presence of the titanium catalyst and the silyl epoxy alcohols obtained in good yields.The method was applied to di- and trisubstituted acyclic vinylsilanes with a methyl group geminal to silicon and cyclic derivatives all give consistently good results.In this novel hydroxy-epoxidation, the regioselectivity of the singlet oxygen ene reaction as well as the diastereoselectivity of the oxygen transfer can be controlled by the steering effects of the silyl group.

One-pot synthesis of α-trimethylsilyl enones from vinylsilanes

Photooxygenation of vinylsilanes in the presence of acetic anhydride and pyridine afforded α-trimethylsilyl enones 1 in moderate to good yields. Since the required starting materials are readily available, the present approach constitutes a useful alterna

ALTERNATIVE SYNTHESES AND DIELS-ALDER REACTIONS OF 2,3-Bis(TRIMETHYLSILYL)BUTA-1,3-DIENE

The title compound has been prepared by two routes and some Diels-Alder reactions of it investigated.

UNSYMMETRICAL MONOPROTECTED α-DIKETONES VIA THE PALLADIUM-CATALYZED VINYLATION OF ACID CHLORIDES WITH ORGANOTIN COMPOUNDS

Under benzyl(chloro)bis triphenylphosphinepalladium(II) catalysis, α-oxygenated vinyltin compounds undergo clean cross coupling with acid chlorides to give α-oxygenated enones which are converted to unsymmetrical α-diketones, butadienyl ethers or substituted methyl vinyl ketones.

A CONVENIENT SYNTHETIC METHOD FOR 3-TRIMETHYLSILYLBUTENONE

Convenient synthetic method for 2-trimethylsilylbutenone from acrolein is presented.