31729-66-5

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Phenylcyclopropanemethanol is utilized as a key intermediate in the synthesis of various pharmaceuticals, leveraging its unique structure to create molecules with specific therapeutic properties.
Used in Organic Chemistry Research:
1-phenylcyclopropanemethanol serves as a valuable subject in organic chemistry research, providing insights into the behavior and reactions of chiral compounds and cyclopropane rings.
Used in the Creation of New Molecules:
1-Phenylcyclopropanemethanol is employed as a building block for the development of new molecules with tailored properties, contributing to advancements in material science and chemical engineering.
Used as a Precursor in Complex Organic Synthesis:
It is used as a precursor in the synthesis of more complex organic molecules, facilitating the production of advanced chemical compounds for various applications.
Used in the Development of New Materials:
1-Phenylcyclopropanemethanol may have potential uses in the development of innovative materials, capitalizing on its unique structural features to engineer novel properties.

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

Upstream product

• 87328-17-4 ethyl 1-phenyl-1-cyclopropanecarboxylate 
• 6120-95-2 1-phenyl-1-cyclopropane carboxylic acid 
• 75-11-6 diiodomethane 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 1007-71-2 1-(1-phenyl-cyclopropyl)-ethanone 
• 935-44-4 1-cyano-1-phenylcyclopropane 
• 140-29-4 phenylacetonitrile 
• 6121-42-2 1-Phenyl-cyclopropanecarboxylic acid methyl ester 
• 570431-52-6 1-phenylcycloprop-2-ene carboxylic acid methyl ester 
• 682760-41-4 (1-phenylcycloprop-2-en-1-yl)methanol 
• 103-79-7 1-phenyl-acetone 
• 63201-02-5 1-phenylcyclopropanecarbonyl chloride 

Downstream Products

• 91132-82-0 carbamic acid-(1-phenyl-cyclopropylmethyl ester) 
• 50462-72-1 [1-(chloromethyl)cyclopropyl]benzene 
• 3365-26-2 1-phenylcyclobutene 
• 1010-24-8 Ethyl-(1-phenyl-cyclopropyl-carbinyl)-ether 
• 88869-42-5 4-Brom-benzolsulfonsaeure-<(1-phenyl-cyclopropyl)-methylester> 
• 6120-95-2 1-phenyl-1-cyclopropane carboxylic acid 
• 50462-74-3 Diethyl-(1-phenylcyclopropyl)methylmalonat 
• 1033617-76-3 O-[(1-phenylcyclopropyl)methyl] N-phenylthiocarbamate 
• 102261-80-3 (CH₂)2C(C₆H₅)CH₂OSO₂CH₃ 
• 1303556-25-3 (R)-(E)-ethyl 5-hydroxy-5-(1-phenylcyclopropyl)pent-2-enoate 

Relevant academic research and scientific papers

Deglycase-activity oriented screening to identify DJ-1 inhibitors

The oncoprotein and Parkinson's disease-associated enzyme DJ-1/PARK7 has emerged as a promiscuous deglycase that can remove methylglyoxal-induced glycation adducts from both proteins and nucleotides. However, dissecting its structural and enzymatic functions remains a challenge due to the lack of potent, specific, and pharmacokinetically stable inhibitors targeting its catalytic site (including Cys106). To evaluate potential drug-like leads against DJ-1, we leveraged its deglycase activity in an enzyme-coupled, fluorescence lactate-detection assay based on the recent understanding of its deglycation mechanism. In addition, we developed assays to directly evaluate DJ-1's esterase activity using both colorimetric and fluorescent substrates. The resulting optimized assay was used to evaluate a library of potential reversible and irreversible DJ-1 inhibitors. The deglycase activity-oriented screening strategy described herein establishes a new platform for the discovery of potential anti-cancer drugs.

Directed RhI-Catalyzed Asymmetric Hydroboration of Prochiral 1-Arylcycloprop-2-Ene-1-Carboxylic Acid Derivatives

A full account on rhodium-catalyzed asymmetric, directed hydroboration of functionalized prochiral cyclopropenes affording enantiomerically enriched cyclopropylboronates is reported. The scope and limitations of two alternate directing groups, ester and carboxamide, are evaluated. It was found that hydroboration of esters appeared to be more sensitive to substitution in the aromatic ring of the substrates. Specifically, ortho-halogens were detrimental for diastereo- and enantioselectivity, possibly because of additional coordination with rhodium. In contrast, more Lewis-basic amide directing groups allowed for stronger chelation to the transition metal, leading to consistently high diastereo- and enantioselectivity in hydroboration across a broader range of substrates.

Electrophilic Bromolactonization of Cyclopropyl Diesters Using Lewis Basic Chalcogenide Catalysts

An efficient and regioselective electrophilic bromolactonization of cyclopropylmethyl diesters using triphenylphosphine sulfide (Ph3PS) or diphenyl selenide (Ph2Se) as the Lewis basic chalcogenide catalyst has been developed. It was observed that Ph3PS favored the formation of anti-diastereomer and yielded the multi-functional γ-lactones. Interestingly, the diastereoselectivity was reversed when using Ph2Se as a catalyst where the syn-product instead of the anti-product was favored. (Figure presented.).

Ruthenium-Catalyzed Deaminative Hydrogenation of Aliphatic and Aromatic Nitriles to Primary Alcohols

The deaminative hydrogenation of nitriles towards alcohols is a useful reaction to transform nitriles into alcohols with NH3 as the sole byproduct. Using the simple and robust RuHCl(CO)(PPh3)3 complex as a catalyst, at low H2 pressures a series of aliphatic and aromatic nitriles could be transformed into the corresponding alcohols. Suitable solvent systems for these reactions were 1,4-dioxane/water and EtOH/water mixtures. In most cases, the selectivity for the alcohols was excellent, and the corresponding amines were formed only in trace amounts.

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.

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.

An improved bouveault-blanc ester reduction with stabilized alkali metals

Significantly improved Bouveault-Blanc conditions for ester reduction have been developed using sodium in silica gel (Na-SG), a free-flowing powder that can be easily handled in the open atmosphere. Primary alcohols were prepared in excellent yield from a variety of aliphatic esters under mild reaction conditions. The chemistry presented here is far safer than the classic Bouveault-Blanc reduction and is competitive with more modern hydride reduction methods.

Survivin inhibitors

Compounds that inhibit survivin, compositions containing the compounds and methods of treating diseases in which survivin is unregulated or overexpressed are disclosed.

Reduction of Cyclopropanecarboxylic Acids by Borane, a Chemoselective Reaction Sensitive to Steric Interactions and Reaction Conditions

A number of cyclopropanecarboxylic acids have been reduced by borane in tetrahydrofuran to the corresponding cyclopropyl alcohols. The yield was sensitive to the steric influence of the substituents attached to the ring, the reaction temperature, and the