5685-38-1

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Phenyl-cyclopropanecarboxylic acid is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs. Its stable and non-reactive nature ensures that it can be incorporated into complex molecular structures without compromising the integrity of the final product.
Used in Organic Compound Synthesis:
In the field of organic chemistry, 2-Phenyl-cyclopropanecarboxylic acid is utilized as an intermediate for the preparation of other organic compounds. Its unique cyclopropane ring structure provides a distinct advantage in the creation of novel chemical entities with potential applications in various industries.
Used in Chemical Research:
2-Phenyl-cyclopropanecarboxylic acid is employed in chemical research to explore its properties and potential applications. 2-PHENYL-CYCLOPROPANECARBOXYLIC ACID's unique structure allows researchers to investigate its reactivity, stability, and interactions with other molecules, which can lead to the discovery of new chemical reactions and the development of innovative materials.
Used in the Preparation of Complex Compounds:
2-PHENYL-CYCLOPROPANECARBOXYLIC ACID is also used as an intermediate in the preparation of complex compounds, where its cyclopropane ring structure can impart specific characteristics to the final product. This makes 2-Phenyl-cyclopropanecarboxylic acid a versatile building block in the synthesis of a wide range of chemical entities with diverse applications.

Upstream product

• 946-38-3 ethyl 2-phenylcyclopropylcarboxylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 766-94-9 vinyl phenyl ether 
• 110-82-7 cyclohexane 
• 84564-98-7 peracide phenyl-2-cyclopropane carboxyloque cis 
• 946-38-3 cis-1-ethoxycarbonyl-2-phenylcyclopropane 
• 5617-74-3 cis-1,2-cyclopropanedicarboxylic acid anhydride 
• 1078-58-6 diphenylzinc 
• 75-47-8 iodoform 
• 140-10-3 cis-cinnamic acid 
• 124-38-9 carbon dioxide 
• 36617-02-4 1-bromo-2-phenylcyclopropane 
• 201230-82-2 carbon monoxide 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 

Downstream Products

• 20030-70-0 methyl 2-phenylcyclopropane-1-carboxylate 
• 100468-15-3 2-Phenyl-cyclopropanecarboxylic acid (3-imidazol-1-yl-propyl)-amide 
• 939-88-8 (+/-)-cis-2-phenyl-cyclopropane-carboxylic acid-⁽¹⁾-amide 
• 939-88-8 rac-(1R,2R)-2-phenylcyclopropanecarboxamide 
• 946-39-4 ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate 
• 946-38-3 cis-1-ethoxycarbonyl-2-phenylcyclopropane 
• 42916-17-6 ((1R,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methanaminium (1R,2S)-2-phenylcyclopropane-1-carboxylate 
• 1265913-03-8 ((1R,5S)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'S,2'S)-2-phenylcyclopropyl)methanone 
• 1265913-05-0 ((1S,5R)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'S,2'S)-2-phenylcyclopropyl)methanone 
• 1265913-11-8 ((1R,5S)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'S,2'R)-2-phenylcyclopropyl)methanone 
• 1265913-09-4 ((1S,5R)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'R,2'S)-2-phenylcyclopropyl)methanone 
• 1265913-13-0 ((1S,5R)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'S,2'R)-2-phenylcyclopropyl)methanone 
• 1265913-16-3 ((1R,5S)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'R,2'S)-2-phenylcyclopropyl)methanone 
• 1265913-20-9 (1R,5S)-5-(3-methoxyphenyl)-2-(((1'S,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonane 

Relevant academic research and scientific papers

A de novo peroxidase is also a promiscuous yet stereoselective carbene transferase

By constructing an in vivo-assembled, catalytically proficient peroxidase, C45, we have recently demonstrated the catalytic potential of simple, de novo-designed heme proteins. Here, we show that C45's enzymatic activity extends to the efficient and stereoselective intermolecular transfer of carbenes to olefins, heterocycles, aldehydes, and amines. Not only is this a report of carbene transferase activity in a completely de novo protein, but also of enzyme-catalyzed ring expansion of aromatic heterocycles via carbene transfer by any enzyme.

Synthesis method of 2-phenylcyclopropane-1-carboxylic acid

The invention provides a synthesis method of 2-phenylcyclopropane-1-carboxylic acid and particularly relates to the technical field of compound preparation. The synthesis method includes steps of: (S1) dissolving triethyl phosphonoacetate and a catalyst in an ether inert solvent, dropwise adding phenylethylene oxide at certain reaction temperature, performing a reaction for certain time at the temperature to obtain an intermediate product, ethyl 2-phenylcyclopropaneformate; (S2) concentrating the reaction liquid in the (S1) to remove organic solvent, adding an alkaline solution for hydrolysis,acidifying the reaction liquid with acid solution, and filtering and drying the product to obtain the final product, 2-phenylcyclopropane-1-carboxylic acid. The synthesis method has simple steps andis improved in yield.

Nickel-Catalyzed Reductive Carboxylation of Cyclopropyl Motifs with Carbon Dioxide

A nickel-catalyzed reductive carboxylation technique for the synthesis of cyclopropanecarboxylic acids has been developed. This user-friendly and mild transformation operates at atmospheric pressure of carbon dioxide and utilizes either organic halides or alkene precursors, thus representing the first example of catalytic reductive carboxylation of secondary counterparts lacking adjacent π-components.

KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE

Disclosed herein are new compounds and compositions and their application as pharmaceuticals for the treatment of diseases. Methods of inhibition of KDMIA, and methods of increasing gamma globin gene expression in a human or animal subject are also provided for the treatment diseases such as sickle cell disease.

(HETERO)ARYL CYCLOPROPYLAMINE COMPOUNDS AS LSD1 INHIBITORS

The invention relates to (hetero)aryl cyclopropylamine compounds, including particularly the compounds of formula (I) as described and defined herein, and their use in therapy, including, e.g., in the treatment or prevention of cancer, a neurological disease or condition, or a viral infection.

Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: Facile access to spiro 3,3′-cyclopropyl oxindoles

The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C-H bonds is described. Various spiro 3,3′-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.

NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes

This publication describes a highly selective oxidation of aldehydes to the corresponding acids or esters. The reaction proceeds under metal-free conditions by using N-heterocyclic carbenes as organocatalysts in combination with environmentally friendly oxygen as the terminal oxidation agent.

Key structural features of cis-cinnamic acid as an allelochemical

1-O-cis-cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the cis-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclohexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated.

Probes for narcotic receptor mediated phenomena. 41. Unusual inverse μ-agonists and potent μ-opioid antagonists by modification of the N-substituent in enantiomeric 5-(3-hydroxyphenyl)morphans

Conformational restraint in the N-substituent of enantiomeric 5-(3-hydroxyphenyl)morphans was conferred by the addition of a cyclopropane ring or a double bond. All of the possible enantiomers and isomers of the N-substituted compounds were synthesized. Opioid receptor binding assays indicated that some of them had about 20-fold higher μ-affinity than the compound with an N-phenylpropyl substituent (Ki = 2-450 nM for the examined compounds with various N-substituents). Most of the compounds acted unusually as inverse agonists in the [35S]GTP-γ-S functional binding assay using nondependent cells that stably express the cloned human μ-opioid receptor. Two of the N-substituted compounds with a cyclopropane ring were very potent μ-opioid antagonists ((+)-29, Ke = 0.17 and (-)-30, Ke =0.3) in the [35S]GTP-γ-S functional binding assay. By comparison of the geometry-optimized structures of the newly synthesized compounds, an attempt was made to rationalize their μ-opioid receptor affinity in terms of the spatial position of N-substituents. This article not subject to U.S. Copyright. Published 2011 by the American Chemical Society.

Biochemical, structural, and biological evaluation of tranylcypromine derivatives as inhibitors of histone demethylases LSD1 and LSD2

LSD1 and LSD2 histone demethylases are implicated in a number of physiological and pathological processes, ranging from tumorigenesis to herpes virus infection. A comprehensive structural, biochemical, and cellular study is presented here to probe the potential of these enzymes for epigenetic therapies. This approach employs tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. This drug is a clinically validated antidepressant known to target monoamine oxidases A and B. These two flavoenzymes are structurally related to LSD1 and LSD2. Mechanistic and crystallographic studies of tranylcypromine inhibition reveal a lack of selectivity and differing covalent modifications of the FAD cofactor depending on the enantiomeric form. These findings are pharmacologically relevant, since tranylcypromine is currently administered as a racemic mixture. A large set of tranylcypromine analogues were synthesized and screened for inhibitory activities. We found that the common evolutionary origin of LSD and MAO enzymes, despite their unrelated functions and substrate specificities, is reflected in related ligand-binding properties. A few compounds with partial enzyme selectivity were identified. The biological activity of one of these new inhibitors was evaluated with a cellular model of acute promyelocytic leukemia chosen since its pathogenesis includes aberrant activities of several chromatin modifiers. Marked effects on cell differentiation and an unprecedented synergistic activity with antileukemia drugs were observed. These data demonstrate that these LSD1/2 inhibitors are of potential relevance for the treatment of promyelocytic leukemia and, more generally, as tools to alter chromatin state with promise of a block of tumor progression.