29480-10-2

Usage

Uses

Used in Organic Synthesis:
1-(4-(trifluoromethyl)phenyl)cyclobutan-1-ol is used as a building block in organic synthesis for creating more complex molecules. The trifluoromethyl group, with its electron-withdrawing properties, influences the reactivity and stability of the compound in various chemical reactions, making it a valuable component in the synthesis process.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 1-(4-(trifluoromethyl)phenyl)cyclobutan-1-ol is used as a key intermediate for the development of new drug candidates. The cyclobutanol structure confers unique properties to the molecule, which can be harnessed to design and synthesize novel pharmaceutical products with potential therapeutic applications.
Overall, 1-(4-(trifluoromethyl)phenyl)cyclobutan-1-ol is a versatile chemical with significant applications in organic synthesis and pharmaceutical development, contributing to the creation of complex molecules and new drug candidates.

Upstream product

• 1191-95-3 cyclobutanone 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 

Downstream Products

• 68963-15-5 (4-(trifluoromethyl)phenyl)cyclobutyl cation 
• 164171-90-8 1-(4-trifluoromethylphenyl)cyclobutene 
• 1272319-97-7 4-hydroxy-1-(4-trifluoromethylphenyl)butan-1-one 
• 62620-71-7 6-(trifluoromethyl)-3,4-dihydronaphthalen-1(2H)-one 
• 61718-86-3 5-oxo-5-[4-(trifluoromethyl)phenyl]pentanenitrile 
• 1086379-78-3 1-(4-(trifluoromethyl)phenyl)cyclobutane-1-carboxylic acid 
• 72216-08-1 2-(4-(trifluoromethyl)phenyl)-1-pyrroline 
• 115464-88-5 2-<4-(trifluoromethyl)phenyl>pyrrole 

Relevant academic research and scientific papers

TFA-Catalyzed [3+2] Spiroannulation of Cyclobutanols: A Route to Spiro[cyclobuta[a]indene-7,1′-cyclobutane] Skeletons

A straightforward method for the synthesis of spiro[cyclobuta[a]indene-7,1′-cyclobutane] derivatives from cyclobutanols has been developed via one-pot [3+2] spiroannulation. A series of new spiro[cyclobuta[a]indene-7,1′-cyclobutane] derivatives are facile

Silver-Promoted Radical Ring-Opening/Pyridylation of Cyclobutanols with N-Methoxypyridinium Salts

The silver-promoted reaction of tertiary cyclobutanols with N-methoxypyridinium salts enables the efficient synthesis of a range of C2-substituted pyridines. The overall process likely occurs by ring-opening (via β-scission) of the cyclobutoxy radical to generate the corresponding γ-keto alkyl radical that itself adds to the pyridinium salt. A wide range of tertiary cyclobutanols and N-methoxypyridinium salts are compatible with the reaction conditions.

Synthesis of 1-Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions

We herein report an efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions. The reaction proceeded without any additional reagents, and nitrogen was generated as the sole by-product. Furthermore, the generated 1-pyrrolines could be continuously transformed into pyrroles, N-Boc-amines, and oxaziridines in an one-pot manner. (Figure presented.).

Nickel-Catalyzed Arylation/Alkenylation of tert-Cyclobutanols with Aryl/Alkenyl Triflates via a C - C Bond Cleavage

Herein, we first present a nickel-catalyzed arylation and alkenylation of tert-cyclobutanols with aryl/alkenyl triflates via a C-C bond cleavage. An array of γ-substituted ketones was obtained in moderate-to-good yields, thus featuring earth-abundant nick

Regio- and Stereoselective Rhodium(II)-Catalyzed C–H Functionalization of Cyclobutanes

Recent developments in controlled C–H functionalization transformations continue to inspire new retrosynthetic disconnections. One tactic in C–H functionalization is the intermolecular C–H insertion reaction of rhodium-bound carbenes. These intermediates can undergo highly selective transformations through the modulation of the ligand framework of the rhodium catalyst. This work describes our continued efforts toward differentiating C–H bonds in the same molecule by judicious catalyst choice. Substituted cyclobutanes that exist as a mixture of interconverting conformers and possess neighboring C–H bonds within a highly strained framework are the targets herein for challenging the current suite of catalysts. Although most C–H functionalization tactics focus on generating 1,2-disubstituted cyclobutanes via substrate-controlled directing-group methods, the regiodivergent methods discussed in this paper provide access to chiral 1,1-disubstituted and cis-1,3-disubstituted cyclobutanes simply by changing the catalyst identity, thus permitting entry to novel chemical space. This study shows how to control site selectivity in C–H functionalization by simply using the correct catalyst. Cyclobutanes were used as the scaffold to illustrate the impact of catalyst control because the core unit is incorporated into various structures of biomedical interest. The catalysts control whether the chemistry occurs at C1 or C3 of the cyclobutane. Traditional synthetic strategies have viewed most C–H bonds as chemically inert and utilize functional groups for transformations. C–H functionalization is an attractive alternative strategy for the synthesis of complex organic molecules because it leads to the possibility of rapidly accessing novel chemical space. To fully develop this alternative approach, it is necessary to identify ways for reacting at specific C–H bonds even when a number of similar C–H bonds may exist in a substrate molecule. It would be particularly beneficial if a collection of catalysts were available, each with a preference for reaction at a specific C–H bond. Over the past few years, we have developed such a collection of catalysts for C–H functionalization chemistry of rhodium-bound carbenes. In this paper, we illustrate how these catalysts can be applied to the selective functionalization of cyclobutanes, leading to the formation of pharmaceutically relevant chiral building blocks.

Catalytic Friedel-Crafts Reactions on Saturated Heterocycles and Small Rings for sp3-sp2 Coupling of Medicinally Relevant Fragments

gem-Diarylheterocycles display a wide range of biological activity. Here we present a systematic study into the formation of 4- to 6-membered O- and N-heterocycles and cyclobutanes bearing the diaryl motif through a catalytic Friedel–Crafts reaction from the corresponding benzylic alcohols. 3,3-Diaryltetrahydrofurans, 4,4-diaryltetrahydropyrans, 3,3-diarylpyrrolidines, 4,4-diaryl-piperidines, as well as diarylcyclobutanes are examined, with results for 3,3-diaryloxetanes and 3,3-diarylazetidines presented for comparison. Three catalytic systems are investigated for each substrate [Ca(II), Li(I) and Fe(III)], across preinstalled aromatic groups of differing electronic character. In most cases examined, the diaryl product is obtained directly from the alcohol with good yields using the most appropriate catalyst system. In the absence of a nucleophile, the olefins from the 5- and 6-membered substrates by elimination of water are obtained under the same reaction conditions.

Manganese-Catalyzed Electrochemical Deconstructive Chlorination of Cycloalkanols via Alkoxy Radicals

A manganese-catalyzed electrochemical deconstructive chlorination of cycloalkanols has been developed. This electrochemical method provides access to alkoxy radicals from alcohols and exhibits a broad substrate scope, with various cyclopropanols and cyclobutanols converted into synthetically useful β- and γ-chlorinated ketones (40 examples). Furthermore, the combination of recirculating flow electrochemistry and continuous inline purification was employed to access products on a gram scale.

Visible-light-induced oxidation/[3 + 2] cycloaddition/oxidative aromatization to construct benzo[ a]carbazoles from 1,2,3,4-tetrahydronaphthalene and arylhydrazine hydrochlorides

An efficient synthesis of benzo[a]carbazoles via visible-light-induced tandem oxidation/[3 + 2] cycloaddition/oxidative aromatization reactions was reported. The benzylic C(sp3)-H of tetrahydronaphthalene was activated through visible-light photoredox catalyst with oxygen as the clean oxidant under mild reaction conditions. This protocol proceeds efficiently with broad substrate scope, and the mechanism study was performed.

Manganese-catalyzed oxidative azidation of cyclobutanols: Regiospecific synthesis of alkyl azides by C-C bond cleavage

A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, oth

Cyclobutene photochemistry. Substituent effects on the photochemistry of 1-phenylcyclobutene

The photochemistry and photophysic of 1-phenylcyclobutene and five aryl-substituted derivatives have been studied in various solvents at room temperature.All six compounds fluoresce with quantum yields in the 0.2-0.3 range in cyclohexane and acetonitrile solution. 1-Phenylcyclobutene undergoes -cycloreversion (γ = 0.09) to yield phenylacetylene upon photolysis in either hydrocarbon or acetonitrile solution, and undergoes (Markovnikov) solvent addition upon irradiation in methanol solution (γ = 0.08) in addition to cycloreversion.Triplet sensitization and quenching experiments indicate that cycloreversion and methanol addition are both excited singlet state processes.None of the six compounds studied undergo ring opening to the corresponding 2-aryl-1,3-butadiene in detectable yield.Quantum yields for cycloreversion in cyclohexane, acetonitrile, and methanol solution and methanol addition have been determined for the six compounds, along with excited singlet state lifetimes.The quantum yields and rate constants for cycloreversion and methanol addition are both enhanced by substitution with electron-donating groups.The variation in the rate constant for cycloreversion with substituent indicates that there is substantial dipolar character developed in the cyclobutenyl ?-bond framework during the reaction, in almost exact correspondence with that developed in the ? system during photoprotonation.No deuterium scrambling is observed in 1-phenylcyclobutene-2,4,4-d3 after photolysis in pentane solution to ca. 80percent conversion, indicating that sleletal rearrangements leading to cyclopropyl carbenes do not occur in the direct photolysis of arylcyclobutene derivatives.A pericyclic mechanism for the photocycloreversion reaction is suggested.Triplet-triplet absorption spectra and triplet lifetimes of 1-phenyl-, 1-(para-methylphenyl)-, and 1-(para-trifluoromethylphenyl)cyclobutene in hydrocarbon solution are also reported. Key words: photochemistry, cyclobutene, fluorescence, -cycloreversion, substituent effects, nanosecond laser flash photolysis, lifetime, triplet state, styrene, photoaddition