72162-99-3

Usage

Uses

Used in Organic Synthesis:
2-(Trimethylsilyl)cyclohex-2-enone is used as a key intermediate for the synthesis of cyclohexyne precursors, which are valuable building blocks in organic chemistry. 2-(trimethylsilyl)cyclohex-2-enone can be converted into these precursors through various reactions, as reported by the Garg and DuBois groups.
Used in the Formation of Silyltriflate Adducts:
The silyl enone can be transformed into a silyltriflate adduct, which is a versatile reagent in organic synthesis. This adduct can be utilized in the presence of cesium fluoride to react with various dienes and dipolarophiles, leading to the formation of complex molecular structures.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, due to the compound's reactivity and utility in organic synthesis, it can potentially be used in the development of pharmaceutical compounds. The cyclohexyne precursors formed from 2-(trimethylsilyl)cyclohex-2-enone could be employed in the synthesis of bioactive molecules with potential applications in the pharmaceutical industry.
Used in Material Science:
Similarly, the cyclohexyne precursors derived from 2-(trimethylsilyl)cyclohex-2-enone could also find applications in material science, where they could be used to create novel materials with specific properties, such as improved strength, flexibility, or chemical resistance.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 50870-61-6 2-bromocyclohex-2-en-1-one 
• 17874-17-8 cyclohex-1-enyl-trimethyl-silane 
• 119547-58-9 1,3-dimethoxy-2-trimethylsilylcyclohex-1-ene 
• 71352-18-6 2-Trimethylsilanyl-cyclohex-2-enol 
• 930-68-7 cyclohexenone 
• 119547-57-8 t-1-iodo-c,t-2,6-dimethoxy-r-1-trimethylsilylcyclohexane 
• 71559-38-1 t-1-iodo-c-2-methoxy-r-1-trimethylsilylcyclohexane 
• 70156-98-8 6-bromo-1,4-dioxaspiro[4,5]dec-6-ene 
• 71559-41-6 2-trimethylsilyl-3-methoxycyclohexene 
• 108-94-1 cyclohexanone 
• 930-66-5 1-chlorocyclohexene 

Downstream Products

• 130199-20-1 Trifluoro-methanesulfonic acid 6-trimethylsilanyl-cyclohexa-1,5-dienyl ester 
• 118297-89-5 3-methyl-2-(trimethylsilyl)cyclohexenyl diphenyl phosphate 
• 118297-88-4 2-(trimethylsilyl)cyclohexenyl diphenyl phosphate 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 79643-73-5 2-(trimethylsilyl)cyclohexanone 
• 1202173-90-7 2-methyl-2-(trimethylsilyl)cyclohexanone 
• 1378309-44-4 2-(hydroxydimethylsilyl)cyclohex-2-enone 
• 207505-17-7 2-(trimethylsilyl)cyclohexen-1-yl triflate 
• 14847-23-5 1,2-cyclohexadiene 
• 1103591-39-4 (E)-2-[(E)-hex-2-enylidene]-3-methylcyclohexanone 

Relevant academic research and scientific papers

Five- and six-membered cyclic α-acylvinyl anionic synthons: Synthesis of α-trimethylsilyl-α,β-unsaturated cycloalkenones and their conversion into 2-(hydroxydimethylsilyl)cycloalk-2-enones through carbon-silicon bond scission

Five- and six-membered α-trimethylsilyl-α,β-unsaturated cycloalkenones were prepared by the Wurtz-Fittig coupling reaction of the corresponding 6-bromo-1,4-dioxaspiro[4,n]cycloalk-6-enes with sodium and chlorotrimethylsilane. Upon treatment with anhydrous

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.

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

Regioselectivity of the Singlet Oxygen Ene Reaction (Schenck Reaction) with Vinylsilanes

The ene reaction of singlet oxygen and vinylsilanes 1 with various substitution patterns and double-bond geometry has been studied. β-Silyl allylic hydroperoxides 2 were the major products of the photooxygenation, accompanied by smaller amounts of α,β-unsaturated ketones 3.The latter derive from decomposition of the regioisomeric α-hydroperoxy silanes 4 by elimination of silanol.Regioselectivities up to 97:3 were observed for vinylsilanes with a methyl group geminal to the silyl group and with cyclic derivatives.Z-Configurated substrates showed lower regioselectivity and reactivity.Elongation of the carbon chain at the geminal position also increased the amount enone formed.These results are rationalized in terms of stereoelectronic effects imposed by the silyl group on the ring-opening of the perepoxide intermediate.

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.

Highly regio- and diastereoselective synthesis of epoxy alcohols directly from vinyl silanes by photooxygenation and titanium-catalyzed oxygen transfer

The photooxygenation of vinyl silanes 1 in the presence of Ti(OiPr)4 afforded regio- and diastereoselectively the epoxy alcohols 3.

ADDITION OF IODINE-BASED ELECTROPHILIC REAGENTS TO SOME VINYLSILANES

The addition of some iodine-based electrophilic reagents to the cyclic vinylsilanes (1) and (4, R=But, R1=H) and (4, R=H, R1=OMe) occurs with high regio- and stereo-specificity to give (2, X=OMe, N3 and NCS) and (5, R=But, R1=H, X=OMe and N3) and (5, R=H, R1=OMe, X=OMe).Similar additions to 2-trimethylsilylhept-1-ene (6) are less efficient and occur with lower regioselectivity.Some of the adducts (2) and (5) have been transformed into functionalised organosilanes.Compounds (10, X=OMe, N3, and NCS) and (12)-(15) are thereby obtained.

Photocycloaddition Chemistry of 2-(Trimethylsilyl)cyclopentenone and 5-(Trimethysilyl)uracil. The Utility of a Trimethylsilyl Group as a Removable Directing Group in Photochemistry

The photocycloaddition reactions of 2-(trimethylsilyl)cyclopentenone with isobutylene, methylenecyclohexane, isopropenyl acetate, propylene, and propyne were investigated. In the first three cases, a regiospecific reaction giving the head-to-tail photoadd