21744-88-7

Usage

Uses

Used in Organic Synthesis:
1-Phenylcyclopropane-1-carbaldehyde is used as a key intermediate in the production of a variety of chemical products. Its unique structure allows for the creation of more complex organic structures, making it a valuable component in the synthesis of numerous compounds.
Used in Pharmaceutical Industry:
1-Phenylcyclopropane-1-carbaldehyde is used as a building block for the synthesis of pharmaceutical compounds. Its reactivity and structural properties enable the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
1-Phenylcyclopropane-1-carbaldehyde is employed as a research tool in the study of organic chemistry, particularly in the investigation of reactions involving strained rings and the development of new synthetic methodologies.
Used in Material Science:
1-Phenylcyclopropane-1-carbaldehyde is utilized in the development of new materials, such as polymers and composites, that exhibit unique properties due to the incorporation of the cyclopropane ring and phenyl group.

InChI:InChI=1/C10H10O/c11-8-10(6-7-10)9-4-2-1-3-5-9/h1-5,8H,6-7H2

Upstream product

• 106-93-4 ethylene dibromide 
• 26939-22-0 2-benzyl-4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazine 
• 4432-63-7 2-phenylacrolein 
• 70775-39-2 dimethylsulfoxonium methylide 
• 935-42-2 (1-phenylcyclopropyl)methylamine 
• 140-29-4 phenylacetonitrile 
• 80234-04-4 2-phenylacrylaldehyde diethyl acetal 
• 6120-95-2 1-phenyl-1-cyclopropane carboxylic acid 
• 56360-93-1 1-phenyl-5-oxabicyclo[2.1.0]pentane 
• 63201-02-5 1-phenylcyclopropanecarbonyl chloride 
• 10575-90-3 N-nitroso-N-cyclopropylurea 
• 100-52-7 benzaldehyde 
• 67074-45-7 2,2-dibromo-1-phenylcyclopropylmethanol 
• 935-44-4 1-cyano-1-phenylcyclopropane 

Downstream Products

• 139633-98-0 1-phenyl-1-ethynylcyclopropane 
• 1303556-25-3 (R)-(E)-ethyl 5-hydroxy-5-(1-phenylcyclopropyl)pent-2-enoate 
• 1258388-75-8 (Z)-(1-(buta-1,3-dienyl)cyclopropyl)benzene 
• 64701-65-1 (E)-2-Methyl-3-(1-phenyl-cyclopropyl)-acrylic acid 
• 64701-72-0 Methyl-(1-methyl-3-phenyl-2-cyclopentenyl)-keton 
• 64701-69-5 (E)-3-Methyl-4-(1-phenyl-cyclopropyl)-but-3-en-2-one 
• 64701-64-0 (E)-3-(1-Phenylcyclopropyl)-2-propensaeure 
• 64701-68-4 (E)-4-(1-Phenylcyclopropyl)-3-buten-2-on 
• 64701-74-2 1-(3-Phenyl-2-cyclopentenyl)ethanol 

Relevant academic research and scientific papers

Photochemical Deracemization at sp3-Hybridized Carbon Centers via a Reversible Hydrogen Atom Transfer

A photochemical deracemization of 5-substituted 3-phenylimidazolidine-2,4-diones (hydantoins) is reported (27 examples, 69%-quant., 80–99% ee). The reaction is catalyzed by a chiral diarylketone which displays a two-point hydrogen bonding site. Mechanistic evidence (DFT calculations, radical clock experiments, H/D labeling) suggests the reaction to occur by selective hydrogen atom transfer (HAT). Upon hydrogen binding, one substrate enantiomer displays the hydrogen atom at the stereogenic center to the photoexcited catalyst allowing for a HAT from the substrate and eventually for its conversion into the product enantiomer. The product enantiomer is not processed by the catalyst and is thus enriched in the photostationary state.

Synthesizing Molecules with Linear Tricyclic 5/5/5 and 6/5/5 Skeletons via [5 + 2 + 1]/Ene Strategy

Report here is the development of a [5 + 2 + 1]/ene strategy for the synthesis of molecules with linear tricyclic 5/5/5 and 6/5/5 skeletons widely found in natural products. The first step of this strategy is applying a Rh-catalyzed [5 + 2 + 1] reaction o

Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst

Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).

Bromomethyl Silicate: A Robust Methylene Transfer Reagent for Radical-Polar Crossover Cyclopropanation of Alkenes

A general protocol for visible-light-induced cyclopropanation of alkenes was developed with bromomethyl silicate as a methylene transfer reagent, offering a robust tool for accessing highly valuable cyclopropanes. In addition to α-aryl or methyl-substituted Michael acceptors and styrene derivatives, the unactivated 1,1-dialkyl ethylenes were also shown to be viable substrates. Apart from realizing the cyclopropanation of terminal alkenes, the methyl transfer reaction has been further demonstrated to be amenable to the internal olefins. The photocatalytic cyclopropanation of 1,3-bis(1-arylethenyl)benzenes was also achieved, giving polycyclopropane derivatives in excellent yields. With late-stage cyclopropanation as the key strategy, the synthetic utility of this transformation was also demonstrated by the total synthesis of LG100268.

Synthesis of 1-hydrocarbon substituted cyclopropyl silyl ketones

The synthesis of cyclopropyl silyl ketones possessing a hydrocarbon group at 1-position of three-membered ring was investigated. The reaction of sulfoxonium ylide with α,β-unsaturated acylsilanes derived from α,β-unsaturated aldehydes did not afford the desired acylsilane derivatives. Instead, the corresponding silyl enol ethers were yielded exclusively. On the other hand, the Corey-Chaykovsky cyclopropanation of α-substituted α,β-unsaturated aldehydes proceeded well to give 1-substituted cyclopropyl aldehydes. The silyl substitution of formyl proton in the obtained aldehydes via umpolung of carbonyl group afforded the target acylsilanes.

Olefin-Migrative Cleavage of Cyclopropane Rings through the Nickel-Catalyzed Hydrocyanation of Allenes and Alkenes

A nickel-catalyzed hydrocyanation triggered by hydronickelation of the carbon-carbon double bonds of allenes followed by cyclopropane cleavage is described. The observed regio- and stereochemistries in the products are strongly influenced by the initial hydronickelation step, and allenyl- and methylenecyclopropanes reacted smoothly to promote the cleavage of cyclopropane. In contrast, this cleavage was not observed with vinylidenecyclopropanes, because the initial hydronickelation does not give a suitable intermediate for cleavage of the cyclopropanes. (Figure presented.).

Design of Potent and Druglike Nonphenolic Inhibitors for Catechol O-Methyltransferase Derived from a Fragment Screening Approach Targeting the S-Adenosyl- l -methionine Pocket

A fragment screening approach designed to target specifically the S-adenosyl-l-methionine pocket of catechol O-methyl transferase allowed the identification of structurally related fragments of high ligand efficiency and with activity on the described orthogonal assays. By use of a reliable enzymatic assay together with X-ray crystallography as guidance, a series of fragment modifications revealed an SAR and, after several expansions, potent lead compounds could be obtained. For the first time nonphenolic and small low nanomolar potent, SAM competitive COMT inhibitors are reported. These compounds represent a novel series of potent COMT inhibitors that might be further optimized to new drugs useful for the treatment of Parkinson's disease, as adjuncts in levodopa based therapy, or for the treatment of schizophrenia.

Biarylphosphonite gold(I) complexes as superior catalysts for oxidative cyclization of propynyl arenes into indan-2-ones

Striking gold: A series of variously functionalized propynyl arenes was smoothly converted into indan-2-ones by a new gold(I)-catalyzed oxidative cyclization process. [LAu]NTf2 (Tf=trifluoromethanesulfonyl) is a superior catalyst both in terms of yield and kinetics for the present transformation. Copyright

INHIBITORS OF HEPATITIS C VIRUS POLYMERASE

The present invention provides, among other things, compounds represented by the general Formula (I) and pharmaceutically acceptable salts thereof, wherein X, Y, R1A, R1B, R2, and R3 are as defined in classes and subclasses herein and compositions (e.g., pharmaceutical compositions) comprising such compounds, which compounds are useful as inhibitors of hepatitis C virus polymerase, and thus are useful, for example, as medicaments for the treatment of HCV infection.

A convenient ring formation of 3-aryl-2,2-dialkyl-2,3-dihydrobenzofurans from phenols and 2-aryl-2,2-dialkylacetaldehydes

A new and simple route for the preparation of 3-aryl-2,2-dialkyl-2,3- dihydrobenzofurans from phenols is described. In the presence of an acid catalyst phenols react with 2-aryl-2,2-dialkylacetaldehydes, prepared in good yield from 2-arylacetonitriles in 2 steps, to give 3-aryl-2,2-dialkyl-2,3- dihydrobenzofurans. Electron-donating substituents were required on the phenols in order to give 3-aryl-2,2-dialkyl-2,3-dihydrobenzofurans in good yield.