38858-72-9

Usage

Uses

Used in Chemical Synthesis:
(3,4-Dihydro-1-naphthyloxy)trimethylsilane is used as a protecting agent for phenolic hydroxyl groups during chemical synthesis. This protection allows for selective reactions to occur at other sites on the molecule, facilitating the synthesis of complex organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3,4-dihydro-1-naphthyloxy)trimethylsilane can be employed as a synthetic intermediate for the development of novel drug candidates. Its ability to protect phenolic hydroxyl groups can be advantageous in the synthesis of complex organic molecules with potential therapeutic applications.
Used in Material Science:
(3,4-Dihydro-1-naphthyloxy)trimethylsilane may also find applications in material science, particularly in the development of new polymers and materials with specific properties. The protected phenol structure can be incorporated into polymer backbones or used as a building block for the creation of advanced materials with tailored characteristics.
Used in Analytical Chemistry:
In analytical chemistry, (3,4-dihydro-1-naphthyloxy)trimethylsilane can be utilized as a derivatization agent for the analysis of phenolic compounds. The protected phenol structure can enhance the detection and quantification of these compounds using various analytical techniques, such as gas chromatography or mass spectrometry.

InChI:InChI=1/C13H18OSi/c1-15(2,3)14-13-10-6-8-11-7-4-5-9-12(11)13/h4-5,7,9-10H,6,8H2,1-3H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 19369-49-4 naphthalene-1(4H)-one 
• 1821-12-1 4-Phenylbutyric acid 
• 2051-95-8 succinylbenzene 
• 71-43-2 benzene 
• 2754-27-0 trimethylsilyl acetate 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 103817-03-4 1-<(trimethylsilyl)methyl>-1,2,4-triazole 
• 34880-70-1 [1-methoxyprop-1-enyloxy]trimethylsilane 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 115262-00-5 [chloro(difluoro)methyl]trimethylsilane 

Downstream Products

• 51015-28-2 8-Methyl-1,2,3,4-tetrahydronaphthalin-1-on 
• 90-15-3 α-naphthol 
• 71019-06-2 2-fluoro-1-tetralone 
• 20841-46-7 2-(phenylthio)-3,4-dihydronaphthalen-1(2H)-one 
• 76643-99-7 2,2-bis(phenylthio)-1-tetralone 
• 138206-92-5 dibenzyl N-(1,2,3,4-tetrahydro-1-oxonaphthalen-2-yl)-N,N'-hydrazinedicarboxylate 
• 7498-87-5 2-phenyl-3,4-dihydro-2H-naphthalen-1-one 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 195064-78-9 trimethyl(1,2,3,4-tetrahydronaphthalen-1-yloxy)silane 
• 108463-22-5 2-(2-Chlorophenyl)-5,6-dihydro-4H-naphtho<1,2-b>pyran-4-one 
• 108463-12-3 1-(2-Chlorophenyl)-3-(1,2,3,4-tetrahydro-1-oxo-2-naphthalenyl)-1,3-propanedione 
• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 64559-97-3 2-hydroxy-1-tetralone 
• 517-25-9 trinitromethane 

Relevant academic research and scientific papers

Reactions of gem-Difluorinated Phosphonium Salts Induced by Light

gem-Difluorinated phosphonium salts, which are readily obtained from aldehydes and difluoromethylene phosphobetaine, can serve as a source of radicals under reductive conditions. An iridium complex or Hantzsch ester was used as a one-electron reducing agent when irradiated with visible light. The fluorinated radicals were trapped with various alkenes, leading to products either via a photoredox cycle (for the iridium catalyst) or via a hydrogen atom transfer (for the Hantzsch ester).

A FACILE ENTREE TO α-OXO SULFINES BY REACTION OF THIONYL CHLORIDE WITH SILYL ENOL ETHERS

Silyl enol ethers derived from 1-indanone, 2-indanone, α-tetralone and 4-chromanone react with thionyl chloride to give α-oxo sulfines (3) which can be either isolated or trapped by a cycloaddition reaction with a diene.

Synthesis of β-nitro ketones from geminal bromonitroalkanes and silyl enol ethers by visible light photoredox catalysis

Various β-nitro ketones, including those bearing a β-tertiary carbon, were prepared from geminal bromonitroalkanes and trimethylsilyl enol ethers of a broad range of ketones by visible light photoredox catalysis, which were then easily converted into β-amino ketones, 1,3-amino alcohols, α,β-unsaturated ketones, β-cyano ketones and γ-nitro ketones.

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.

Photoinduced Deaminative Alkylation for the Synthesis of γ-Ketoesters via Electron Donor–Acceptor Complex Formation

Visible-light-induced deaminative alkylation of Katritzky salts with silyl enol ethers has been developed. The reaction can proceed efficiently through electron donor–acceptor complex formation, avoiding the use of precious metal complexes or synthetically elaborate organic dyes. A series of functionalized γ-ketoesters was successfully obtained with good functional group tolerance and compatibility under mild and straightforward conditions.

The Cyclopropane Ring as a Reporter of Radical Leaving-Group Reactivity for Ni-Catalyzed C(sp3)-O Arylation

The ability to understand and predict reactivity is essential for the development of new reactions. In the context of Ni-catalyzed C(sp3)-O functionalization, we have developed a unique strategy employing activated cyclopropanols to aid the design and optimization of a redox-active leaving group for C(sp3)-O arylation. In this chemistry, the cyclopropane ring acts as a reporter of leaving-group reactivity, since the ring-opened product is obtained under polar (2e) conditions, and the ring-closed product is obtained under radical (1e) conditions. Mechanistic studies demonstrate that the optimal leaving group is redox-active and are consistent with a Ni(I)/Ni(III) catalytic cycle. The optimized reaction conditions are also used to synthesize a number of arylcyclopropanes, which are valuable pharmaceutical motifs.

Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate

A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce di- or tri- substituted olefins. It is worth noting that this approach exhibited good tolerance to highly reactive tertiary alcohols, which could not survive in other reported routes for converting carbonyl compounds to olefins. This method also showed good regio- and stereo-selectivity for olefin products. Preliminary mechanistic studies indicated that the reaction was accomplished through nickel catalyzed C—O activation of enolates, thus offering helpful contribution to current enol chemistry.

C?O coupling of Malonyl Peroxides with Enol Ethers via [5+2] Cycloaddition: Non-Rubottom Oxidation

Malonyl peroxides act both as oxidants and reagents for C?O coupling in reactions with methyl and silyl enol ethers. In the proposed conditions, the oxidative C?O coupling of malonyl peroxides with enol ethers selectively proceeds, bypassing the traditional Rubottom hydroxylation of enol ethers by peroxides. It was observed that the oxidative [5+2] cycloaddition of malonyl peroxides and enol ethers is the key stage of the discovered process. Oxidative C?O coupling of silyl enol ethers leads to the formation of α-acyloxyketones with a free carboxylic acid group. A specially developed preparative one-pot procedure transforms ketones via silyl enol ethers formation and the following coupling into α-acyloxyketones with yields 35–88%. The acid-catalyzed coupling with methyl enol ethers gives remarkable products while retaining the easily oxidizable enol fragment. Furthermore, these molecules contain a free carboxylic acid group, thus these nontrivial products contain two usually incompatible acid and enol ether groups. (Figure presented.).

An Electrophilic Trifluoromethylthiolation of Silylenol Ethers and β-Naphthols with Diethylaminosulfur Trifluoride and (Trifluoromethyl)trimethylsilane

An efficient and general trifluoromethylthiolation of silylenol ethers and β-naphthols have been accomplished employing the combination of diethylaminosulfur trifluoride (DAST) and (trifluoromethyl)trimethylsilane (CF3TMS) as source of electrophilic trifluoromethylthio moiety for the synthesis of α-trifluoromethylthiolated carbonyl compounds and β-naphthols in good yields. Important features of this method include wide functional group tolerance and use of readily available DAST/CF3TMS. Potential of the methodology was demonstrated via the synthesis of α-trifluoromethylthiolated (+)-4-cholesten-3-one and naphthoquinone. (Figure presented.).

Synthesis of 3-Fluoropyridines via Photoredox-Mediated Coupling of α,α-Difluoro-β-iodoketones with Silyl Enol Ethers

A method for the synthesis of diversely substituted 3-fluoropyridines from two ketone components is described. The reaction involves photoredox coupling of α,α-difluoro-β-iodoketones with silyl enol ethers catalyzed by fac-Ir(ppy)3 under blue LED irradiation with subsequent one-pot condensation with ammonium acetate. Based on cyclic voltammetry studies, it was determined that α,α-difluoro-β-iodoketones are reduced notably easier compared to 2,2,2-trifluoro-1-iodoethane, which may be ascribed to the influence of the carbonyl group.