935-64-8

Usage

Physical state

White solid

Odor

Pleasant

Usage

Fragrance ingredient in perfumes and cosmetics

Functional group

Hydroxyl (-OH)

Derivation

Cyclobutane (four-membered carbon ring)

Aromatic properties

Due to the attached phenyl group

Application

Building block in organic synthesis

Industries

Pharmaceutical, agricultural, and chemical

Value

Versatile and valuable chemical

InChI:InChI=1/C10H12O/c11-10(7-4-8-10)9-5-2-1-3-6-9/h1-3,5-6,11H,4,7-8H2

Upstream product

• 108-86-1 bromobenzene 
• 1191-95-3 cyclobutanone 
• 4392-30-7 phenylcyclobutane 
• 130996-80-4 C₈₀H₉₆O₈*2C₁₀H₁₂O 
• 130996-79-1 1,1,6,6-Tetraphenyl-hexa-2,4-diyne-1,6-diol; compound with 1-phenyl-butan-1-one 
• 591-51-5 phenyllithium 
• 67-56-1 methanol 
• 495-40-9 propiophenone 
• 935-44-4 1-cyano-1-phenylcyclopropane 
• 140-29-4 phenylacetonitrile 
• 100-58-3 phenylmagnesium bromide 
• 1034-83-9 (1-phenylcyclopropyl)methyl p-toluenesulfonate 
• 91495-73-7 Essigsaeure-(1-phenyl-cyclobutylester) 
• 935-42-2 (1-phenylcyclopropyl)methylamine 

Downstream Products

• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 33553-82-1 4-chloro-1-phenyl-1-butanol 
• 1226042-17-6 1-phenyl-4-(p-tolyl)butan-1-one 
• 65-85-0 benzoic acid 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 

Relevant academic research and scientific papers

1,1′-diphenyl-1,1′-bicyclopropyl and 1,1′-diphenyl-1,1′-bicyclobutyl

The molecules of 1,1′-diphenyl-1,1′-bicyclopropyl, C18H18, and 1,1′-diphenyl-1,1′-bicyclobutyl, C20H22, each possess a crystallographic centre of symmetry. Both molecules adopt the trans conformation. The cyclop

Iron-Catalyzed Ring Expansion of Cyclobutanols for the Synthesis of 1-Pyrrolines by Using MsONH3OTf

The synthesis of 1-pyrrolines from cyclobutanol derivatives and an aminating reagent (MsONH3OTf) has been developed. This one-pot procedure achieves C–N bond/C═N bond formation via ring expansion. A series of 1-pyrroline derivatives are synthes

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

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.).

Terminal Trifluoromethylation of Ketones via Selective C-C Cleavage of Cycloalkanols Enabled by Hypervalent Iodine Reagents

We report the first terminal trifluoromethylation at aryl and alkyl ketones' ?, or more remote sites via the selective C-C bond cleavage of cycloalkanols. The noncovalent interactions between alcohols and hypervalent iodines(III) reagents were disclosed to activate both alcohols and the Togni I reagent in the dual photoredox/copper catalysis for the transformation. This reaction was scalable to the gram-scale synthesis, applicable to the structurally complex steroid trifluoromethylation, and extendable to the pentafluoroethylation.

Regioselective Electrochemical Cyclobutanol Ring Expansion to 1-Tetralones

A mild electrochemical method for the regioselective preparation of 1-tetralones under environmentally friendly conditions from readily available cyclobutanols was developed. A series of aromatic- and heteroaromatic-fused 1-tetralones was accessed through ring expansion of the functionalized cyclobutanols via electrochemical generation of alkoxy radicals and intramolecular cyclization.

Selective cine -arylation of tert -cyclobutanols with indoles enabled by nickel catalysis

In previous literature, tert-cyclobutanols are widely studied for C-C bond activation exclusively leading to the formation of ordinary γ-substituted ketones. Herein, we first report a nickel-catalyzed cine-arylation of tert-cyclobutanols with indoles to access β-aryl ketones with an unusual site-selectivity at the C3-position of tert-cyclobutanols. The reaction features earth-abundant nickel catalysis, excellent regioselectivity, high atom-economy, and broad substrate scope.

Nickel-Catalyzed Cross-Coupling of Aryl Pivalates with Cyclobutanols Involving C—O and C—C Bond Cleavage?

An efficient nickel-catalyzed cross-coupling of aryl pivalates with cyclobutanols is described. The use of Ni(cod)2/PCy3/base as the catalytic system enables the cleavage of inert C—O bond and C—C bond under mild conditions, thus providing a facile access to γ-arylated ketones in generally good to excellent yields. This transformation is also characterized by wide substrate scope and functional group compatibility, for example, methoxy, N,N-dimethylamino, keto, ester, fluoro and TMS groups are well-tolerated during the reaction process.

Concurrent Formation of N-H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C-C Bond Cleavage of β-Hydroxy Azides

A commercial cyclopentadienylrutenium dicarbonyl dimer ([CpRu(CO)2]2) efficiently catalyzes the formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy azides via C-C bond cleavage under visible light. Density functional theory calculations for the cleavage reaction support the mechanism involving chelation of alkoxy azide species and liberation of nitrogen as the driving force. The synthetic utility of the reaction was demonstrated by a new amine synthesis promoted by chemoselective allylation of imine and synthesis of isoquinoline.

Supramolecularly regulated copper-bisoxazoline catalysts for the efficient insertion of carbenoid species into hydroxyl bonds

The catalytic insertion of copper carbenoids into O-H bonds affords synthetically useful α-alkyl/aryl-α-alkoxy/aryloxy derivatives. Herein, the design, preparation and application of supramolecularly regulated copper(i) complexes of bisoxazoline ligands is reported. We have demonstrated that the catalytic performance of these systems can be modulated by the use of an external molecule (i.e.the regulation agent), which interacts with a polyethyleneoxy chain on the ligand (i.e.the regulation site)viasupramolecular interactions. This approach has been applied to an array of structurally diverse alcohols (cycloalkyl, alkyl and aryl derivatives). Moreover, we have used this methodology to synthesise advanced synthetic intermediates of biologically relevant compounds.