48126-51-8

Usage

Uses

Used in Organic Synthesis:
(1R,2S)-2-phenylcyclopropane-1-carboxylic acid is utilized as a key building block in organic synthesis for the creation of more complex molecules. Its unique structure and reactivity make it a valuable component in the synthesis of various organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (1R,2S)-2-phenylcyclopropane-1-carboxylic acid serves as a crucial intermediate in the development of new drugs and biologically active compounds. Its cyclopropane ring offers a potentially interesting scaffold for medicinal chemists to explore novel therapeutic agents.
Used in Drug Development:
(1R,2S)-2-phenylcyclopropane-1-carboxylic acid is employed as a starting material in the synthesis of pharmaceuticals, where its chiral nature allows for the development of enantiomerically pure drugs. This is important for ensuring the desired biological activity and minimizing potential side effects associated with less selective compounds.

Upstream product

• 97-71-2 (1R,2S)-ethyl 2-phenylcyclopropane-1-carboxylate 
• 100-42-5 styrene 
• 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 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 1759-53-1 cyclopropanecarboxylic acid 
• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 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 
• 5617-74-3 cis-1,2-cyclopropanedicarboxylic acid anhydride 
• 1078-58-6 diphenylzinc 
• 201230-82-2 carbon monoxide 

Downstream Products

• 1265913-09-4 ((1S,5R)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'R,2'S)-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 
• 1265913-25-4 (1S,5R)-5-(3-methoxyphenyl)-2-(((1'R,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonane 
• 1265913-30-1 (1R,5S)-5-(3-methoxyphenyl)-2-(((1'R,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonane 
• 1265968-40-8 3-((1S,5R)-2-(((1'R,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonan-5-yl)phenol 
• 1265968-43-1 3-((1R,5S)-2-(((1'R,2'S)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonan-5-yl)phenol 
• 1402883-74-2 ethyl 3-oxo-3-((1R,2S)-2-phenylcyclopropyl)propanoate 
• 883894-57-3 2-amino-3-methyl-6-((1S,2S)-2-phenylcyclopropyl)pyrimidin-4(3H)-one 
• 1402883-75-3 C₁₃H₁₃N₃O 
• 883894-58-4 C₁₃H₁₃N₃O 
• 625389-83-5 (1R,2S)-1-[4-(2,4-dimethylphenyl)piperazyl]carbonyl-2-phenylcyclopropane 
• 5682-61-1 (1S,2S)-2-phenylcyclopropanecarboxylic acid methyl ester 
• 5682-61-1 (1S,2R)-2-phenylcyclopropanecarboxylic acid methyl ester 
• 946-39-4 ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate 

Relevant academic research and scientific papers

Asymmetric C-H functionalization of cyclopropanes using an isoleucine-NH2 bidentate directing group

The systematic investigation of substrate-bound α-amino acid auxiliaries has resulted in catalytic asymmetric C-H functionalization of cyclopropanes enabled by amino acid amides as chiral bidentate directing groups. The use of an Ile-NH2 auxili

Gold(I)-catalyzed stereoselective olefin cyclopropanation

A triphenylphosphinegold(I)-catalyzed cyclopropanation of olefins using propargyl esters as gold(I)-carbene precursors is reported. This reaction provided the basis for the use of a DTBM-SEGPHOS gold(I) complex as a catalyst in the enantioselective (up to

Stereoselective Functionalization of Racemic Cyclopropylzinc Reagents via Enantiodivergent Relay Coupling

Efficient construction of optically pure molecules from readily available starting materials in a simple manner is an ongoing goal in asymmetric synthesis. As a straightforward route, transition-metal-catalyzed enantioconvergent coupling between widely available secondary alkyl electrophiles and organometallic nucleophiles has emerged as a powerful strategy to construct chiral center(s). However, the scope of racemic secondary alkylmetallic nucleophiles for this coupling remains limited in specific substrates because of the difficulties in stereoselective formation of the key alkylmetal intermediates. Here, we report an enantiodivergent strategy to efficiently achieve an array of synthetically useful chiral cyclopropanes, including chiral fluoroalkylated cyclopropanes and enantiomerically enriched cyclopropanes with chiral side chains, from racemic cyclopropylzinc reagents. This strategy relies on a one-pot, two-step enantiodivergent relay coupling process of the racemic cis-cyclopropylzinc reagents with two different electrophiles, which involves kinetic resolution of racemic cis-cyclopropylzinc reagents through a nickel-catalyzed enantioselective coupling with alkyl electrophiles, followed by a stereospecific relay coupling of the remaining enantiomeric cyclopropylzinc reagent with various electrophiles, to produce two types of functionalized chiral cyclopropanes with opposite configurations on the cyclopropane ring. These chiral cyclopropanes are versatile synthons for diverse transformations, rendering this strategy effective for obtaining structurally diversified molecules of medicinal interest.

PdII-Catalyzed Enantioselective C(sp3)?H Activation/Cross-Coupling Reactions of Free Carboxylic Acids

PdII-catalyzed enantioselective C(sp3)?H cross-coupling of free carboxylic acids with organoborons has been realized using either mono-protected amino acid (MPAA) ligands or mono-protected aminoethyl amine (MPAAM) ligands. A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners to provide chiral carboxylic acids. This reaction provides an alternative approach to the enantioselective synthesis of cyclopropanecarboxylic acids and cyclobutanecarboxylic acids containing α-chiral tertiary and quaternary stereocenters. The utility of this reaction was further demonstrated by converting the carboxylic acid into cyclopropyl amine without loss of optical activity.

PD(II)-CATALYZED ENANTIOSELECTIVE C-H ARYLATION OF FREE CARBOXYLIC ACIDS

The invention includes procedures for stereoselective β-arylation of carboxylic acids having a β-carbon atom. For example, stereoselective arylation procedures include the following reactions: (I)

Pd(II)-Catalyzed Enantioselective C(sp3)-H Arylation of Free Carboxylic Acids

A monoprotected aminoethyl amine chiral ligand based on an ethylenediamine backbone was developed to achieve Pd-catalyzed enantioselective C(sp3)-H arylation of cyclopropanecarboxylic and 2-aminoisobutyric acids without using exogenous directing groups. This new chiral catalyst affords new disconnection for preparing diverse chiral carboxylic acids from simple starting materials that are complementary to the various ring forming approaches.

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.

ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds of Formula (IVA), or a salt thereof, and pharmaceutical formulations (pharmaceutical compositions) comprising those compounds, or a salt thereof: Formula (IVA), wherein "RIa", "RIb", "RIc", "RId", "RIe", are defined herein above, which compounds are believed suitable for use in positive modulation of the alpha 7 nicotinic acetylcholine receptor (α7 nAChR) receptors, for example, those found in the cerebral cortex and the hippocampus. Such compounds and pharmaceutical formulations are believed to be useful in treatment or management of neurodegenerative diseases, for example, Alzheimer's disease (AD), schizophrenia, and Parkinson's disease (PD), or movement disorders arising from use of certain medications used in the treatment or management of Parkinson's 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.