19980-43-9

Usage

Uses

Used in Chemical Synthesis Studies:
1-(Trimethylsiloxy)cyclopentene is used as a reagent for chemical synthesis due to its unique properties that facilitate specific reactions and transformations. Its trimethylsiloxy group provides a handle for further functionalization, making it a versatile building block in the synthesis of complex organic molecules.
In the Pharmaceutical Industry:
1-(Trimethylsiloxy)cyclopentene is used as an intermediate in the synthesis of various pharmaceutical compounds. Its ability to undergo specific reactions allows for the creation of novel drug candidates with potential therapeutic applications.
In the Material Science Industry:
1-(Trimethylsiloxy)cyclopentene is used as a precursor in the development of advanced materials, such as polymers and composites, due to its potential to be incorporated into their structures and influence their properties.
In the Agrochemical Industry:
1-(Trimethylsiloxy)cyclopentene is used as a starting material for the synthesis of agrochemicals, including pesticides and herbicides, where its unique properties can contribute to the development of more effective and environmentally friendly products.

Purification Methods

If too impure as seen by the NMR spectrum, then dissolve it in 10 volumes of pentane, shake with cold NaHCO3 (3 x 500mL), then 1.5M HCl (200mL) and aqueous NaHCO3 (200mL) again, dry (Na2SO4), filter, evaporate and distil it through a short Vigreux column (p 11). 1H NMR: (CDCl3) : 0.21 (s, 9H), 1.55 (m, 2H), 1.69 (m, 2H), 2.05 (br d, 4H) and 4.88 (br s, 1H). GLPC in a 6ft x 1/8inch with 3% SP2100 on 100-120 mesh Supelcoport column should give one peak. Store dry. [For the cyclohexene analogue see Varghese et al. Org Synth Coll Vol VIII 460 1993.]

InChI:InChI=1/C8H16OSi/c1-10(2,3)9-8-6-4-5-7-8/h6H,4-5,7H2,1-3H3

Upstream product

• 7449-74-3 N-methyl-N-trimethylsilylacetamide 
• 120-92-3 cyclopentanone 
• 75-77-4 chloro-trimethyl-silane 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 933-06-2 1-acetoxycyclopentene 
• 42161-96-6 1-cyclopropyl-1-(trimethylsilyloxy)ethene 
• 43112-38-5 3-(trimethylsilyl)-2-oxazolidinone 
• 2857-97-8 trimethylsilyl bromide 
• 16029-98-4 trimethylsilyl iodide 
• 18306-29-1 bis(trimethylsilyl)sulphate 
• 34880-70-1 [1-methoxyprop-1-enyloxy]trimethylsilane 
• 114643-78-6 4-Benzyl-1-trimethylsilanyl-pyridinium; iodide 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 54322-80-4 2-(3-Phenyl-1-trimethylsilanyloxy-propyl)-cyclopentanone 
• 54322-81-5 2-(3-phenylpropylidene)-cyclopentanone 
• 72216-44-5 2-(1-Methyl-1-cyclohexyl)cyclopentanon 
• 43108-70-9 (2R*, 1'R*)-2-(hydroxy(phenyl)methyl)cyclopentanone 
• 43108-71-0 anti-2-<(hydroxy)(phenyl)methyl>cyclopentanone 
• 39745-17-0 2-(3-oxo-1,3-diphenylpropyl)cyclopentanone 
• 52190-40-6 2-(phenylthio)cyclopentanone 
• 43108-72-1 2-(1-Benzyl-1-hydroxy-2-phenyl-ethyl)-cyclopentanone 
• 51004-14-9 2-(2-oxocyclopentyl)acetonitrile 
• 70461-41-5 2-phenyl-4,5,6,7-tetrahydrocyclopentapyran-4-one 
• 60769-96-2 (5R*)-4-benzoyl-1,5-dihydro-3-hydroxy-5-(2-oxocyclopentyl)-2H-pyrrol-2-one 
• 930-30-3 cyclopent-2-enone 

Relevant academic research and scientific papers

Enyne-2-pyrone [4 + 4]-Photocycloaddition: Sesquiterpene Synthesis and a Low-Temperature Cope Rearrangement

Intramolecular [4 + 4] photoreaction of 2-pyrones with a 1,3-enyne yields an unstable 1,2,5-cyclooctatriene product. Without a C4 pyrone substituent, 1,3-hydrogen migration converts the allene to a 1,3-diene, with a skeleton related to dactylol. With methoxy substitution, Cope rearrangement yields a nine-membered ring fused to a cyclobutane. Both structures were confirmed by X-ray crystallography. The Cope rearrangement is apparently reversible, reforming the allene which undergoes a proton shift to the more stable 1,3-diene product.

Kinetics of the Siloxyvinylcyclopropane Rearrangement Using a Micro Stirred Flow Reactor

The kinetics of the thermal rearrangement of 1-(1-(trimethylsiloxy)cyclopropyl)cyclopentene (3), 5-methyl-1-(1-(trimethylsiloxy)cyclopropyl)cyclopentene (5), 1-cyclopropyl-1-(trimethylsiloxy)ethylene (7), and 1-((Z)-2-methyl-1-(trimethylsiloxy)cyclopropyl)cyclopentene (9) was investigated on a micro stirred flow apparatus.Siloxyvinylcyclopropanes 3, 5, and 7 rearrange cleanly to their respective cyclopentyl enol silyl ethers with a calculated ΔG% (350 deg C) of 43.8 kcal/mol for 3, 42.9 kcal/mol for 5, and 51.3 kcal/mol for 7.Siloxyvinylcyclopropane 9 rearranged to4-cyclopentylidene-4-(trimethylsiloxy)but-1-ene (10) via the homo 1,5 hydrogen shift with a calculated ΔG% (350 deg C) of 39.2 kcal/mol.A comparison of the ΔG%-s for the rearrangement of siloxyvinylcyclopropanes is made with those of other substituted vinylcyclopropanes.

Boron Trifluoride-Mediated Cycloaddition of 3-Bromotetrazine and Silyl Enol Ethers: Synthesis of 3-Bromo-pyridazines

Pyridazines are important scaffolds for medicinal chemistry or crop protection agents, yet the selective preparation of 3-bromo-pyridazines with high regiocontrol remains difficult. We achieved the Lewis acid-mediated inverse electron demand Diels-Alder reaction between 3-monosubstituted s-tetrazine and silyl enol ethers and obtained functionalized pyridazines. In the case of 1-monosubstituted silyl enol ethers, exclusive regioselectivity was observed. Downstream functionalization of the resulting 3-bromo-pyridazines was demonstrated utilizing several cross-coupling protocols to synthesize 3,4-disubstituted pyridazines with excellent control over the substitution pattern.

1,2-Carbopentafluorophenylation of Alkynes: The Metallomimetic Pull-Push Reactivity of Tris(pentafluorophenyl)borane

We report the novel single-step 1,2-dicarbofunctionalization of an arylacetylene with an allylsilane and tris(pentafluorophenyl)borane [B(C6F5)3] involving C?C bond formation with C?H bond scission at the β-position to the silicon atom of an allylsilane and B→C migration of a C6F5 group. The 1,2-carbopentafluorophenylation occurs smoothly without the requirement for a catalyst or heating. Mechanistic studies suggest that the metallomimetic “pull-push” reactivity of B(C6F5)3 imparts consecutive electrophilic and nucleophilic characteristics to the benzylic carbon of the arylacetylene. Subsequent photochemical 6π-electrocyclization affords tetrafluoronaphthalenes, which are important in the pharmaceutical and materials sciences. Owing to the unique reactivity of B(C6F5)3, the 1,2-carbopentafluorophenylation using 2-substituted furan proceeded with ring opening, and the reaction using silyl enolates formed a C?C bond with C?O bond scission at the silyloxy-substituted carbon.

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.

Visible light-mediated intermolecular [2 + 2] photocycloaddition of 1-aryl-2-nitroethenes and olefins

Despite the importance of cyclobutanes there are not many direct [2 + 2] photocycloaddition reactions which can be performed with visible light in the absence of a catalyst. A notable exception is the reaction of 1-aryl-2-nitroethenes and olefins which can be performed at a wavelength of λ = 419 nm or λ = 424 nm in CH2Cl2 as the solvent. In the present study, a total of 15 1-aryl-2-nitroethenes were found to undergo a [2 + 2] photocycloaddition with 2,3-dimethyl-2-butene (28-86% yield) and a set of 12 olefins was studied in their photocycloaddition to 1-phenyl-2-nitroethene (37-88% yield). All mechanistic results are in agreement with a triplet reaction pathway and with the intermediacy of a 1,4-diradical.

Unprecedented alkylation of silicon enolates with alcohols via carbenium ion formations catalyzed by tin hydroxide-embedded montmorillonite

The solid acid, tin hydroxide-embedded montmorillonite, catalyzes the unprecedented alkylation of various silicon enolates with primary, secondary and tertiary benzylic alcohols as well as secondary allylic alcohols. The acid catalysis of Sn-Mont was not only higher than that of the other ion-exchanged montmorillonites (M-Mont; M?=?H, Ti, Fe and Al), but also higher than that of the typical homogeneous acid catalysts such as BF3·OEt2, TMSOTf and TfOH.

Stereoselective and Regioselective Pinacol-Type Rearrangement of a Fused Bicyclic Oxetanol Scaffold

The Paternò-Büchi reaction between benzaldehyde and trimethylsilyloxycyclopentene gave access to an unprecedented silyl ether derivative of 6-oxabicyclo[3.2.0]heptan-1-ol. The bicyclic structure underwent selective reductive ring opening and acid-catalyzed pinacol-type rearrangement reactions with complete regioselectivity, accompanied by moderate to excellent mechanism-dependent diastereoselectivity.

Chiral Br?nsted Acid as a True Catalyst: Asymmetric Mukaiyama Aldol and Hosomi-Sakurai Allylation Reactions

Highly diastereo- and enantioselective Mukaiyama aldol reaction catalyzed by a new chiral Br?nsted acid, N-(perfluorooctanesulfonyl)thiophosphoramide, is described. The perfluorooctyl substituent on the sulfonyl group of the catalyst plays an essential role in the stereoselection. The catalyst also allows the asymmetric Hosomi-Sakurai allylation, which has been considerably challenging due to the low reactivity of allylsilanes. 29Si and 31P NMR monitoring reveals the characteristic feature of the thiophosphoramide catalyst, acting as a strong Br?nsted acid even in the presence of excess silyl nucleophiles, which cannot be found in other related phosphoric acid analogues.

Ring-contraction strategy for the practical, scalable, catalytic asymmetric synthesis of versatile γ-quaternary acylcyclopentenes

Contraction action! A simple protocol for the catalytic asymmetric synthesis of highly functionalized γ-quaternary acylcyclopentenes (see schematic) in up to 91 % overall yield and 92 % ee has been developed. The reaction sequence employs a palladium-catalyzed enantioselective alkylation reaction and exploits the unusual stability of β-hydroxy cycloheptanones to achieve a general and robust method for performing two-carbon ring contractions. Copyright