3471-10-1

Basic information

• Product Name: (1R)-2α-Phenylcyclopropane-1β-carboxylic acid
• Synonyms: (1R)-2α-Phenylcyclopropane-1β-carboxylic acid;(1R,2R)-2-Phenylcyclopropanecarboxylic acid;(1R)-2α-Phenylcyclopropane-1&beta
• CAS NO: 3471-10-1
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Mol File: 3471-10-1.mol
• Article Data: 40

Chemical Properties

• Melting Point: 92 °C
• Boiling Point: 317.1±31.0 °C(Predicted)
• Appearance: /
• Density: 1.250±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.57±0.10(Predicted)
• CAS DataBase Reference: (1R)-2α-Phenylcyclopropane-1β-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-2α-Phenylcyclopropane-1β-carboxylic acid(3471-10-1)
• EPA Substance Registry System: (1R)-2α-Phenylcyclopropane-1β-carboxylic acid(3471-10-1)

Safety Data

• Hazardous Substances Data: 3471-10-1(Hazardous Substances Data)

Usage

General Description

(1R)-2α-Phenylcyclopropane-1β-carboxylic acid is a chemical compound with a cyclopropane ring and a carboxylic acid functional group. It is also known as cis-2-phenylcyclopropane-1-carboxylic acid and is used in the synthesis of various pharmaceuticals and organic compounds. (1R)-2α-Phenylcyclopropane-1β-carboxylic acid has potential applications in the field of medicinal chemistry and drug development due to its unique structure and properties. It is important for researchers and chemists to study and understand the reactivity and biological activities of (1R)-2α-Phenylcyclopropane-1β-carboxylic acid in order to explore its potential uses in various industries.

Upstream product

• 97-71-2 (1R,2R)-2-phenyl-cyclopropanecarboxylic acid ethyl ester 
• 82263-48-7 trans-2- phenylcyclopropane-1-carbaldehyde 
• 133124-20-6 (2R,4S)-(+)-5,5-dimethyl-4-phenyl-2-(trans-2-phenylcyclopropyl)-1,3-dioxane 
• 573968-14-6 (R,R)-trans-2-phenyl-cyclopropane-1-carboxylic acid benzyl ester 
• 99267-79-5 (4R,5R)-2-((1R,2R)-2-Phenyl-cyclopropyl)-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester 
• 946-39-4 ethyl rac-(1S,2S)-2-phenylcycloproanecarboxylate 
• 4660-02-0 (+/-)-trans-2-phenylcyclopropanecarbonitrile 
• 14371-10-9 (E)-3-phenylpropenal 
• 100-42-5 styrene 
• 623-73-4 diazoacetic acid ethyl ester 
• 766-94-9 vinyl phenyl ether 
• 5617-74-3 cis-1,2-cyclopropanedicarboxylic acid anhydride 
• 1078-58-6 diphenylzinc 
• 75-47-8 iodoform 

Downstream Products

• 185256-47-7 (-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester 
• 95-62-5 (1R,2S)-1-amino-2-phenylcyclopropane 
• 1265913-01-6 ((1S,5R)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'R,2'R)-2-phenylcyclopropyl)methanone 
• 1265913-07-2 ((1R,5S)-5-(3-methoxyphenyl)-2-azabicyclo[3.3.1]nonan-2-yl)-((1'R,2'R)-2-phenylcyclopropyl)methanone 
• 1265913-18-5 (1S,5R)-5-(3-methoxyphenyl)-2-(((1'R,2'R)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonane 
• 1265913-24-3 (1R,5S)-5-(3-methoxyphenyl)-2-(((1'R,2'R)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonane 
• 1265968-36-2 3-((1S,5R)-2-(((1'R,2'R)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonan-5-yl)phenol 
• 1265968-39-5 3-((1R,5S)-2-(((1'R,2'R)-2-phenylcyclopropyl)methyl)-2-azabicyclo[3.3.1]nonan-5-yl)phenol 
• 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 
• 1265913-09-4 ((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 

Relevant articles and documents

Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes

The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.

Gram-Scale Synthesis of Chiral Cyclopropane-Containing Drugs and Drug Precursors with Engineered Myoglobin Catalysts Featuring Complementary Stereoselectivity

Engineered hemoproteins have recently emerged as promising systems for promoting asymmetric cyclopropanations, but variants featuring predictable, complementary stereoselectivity in these reactions have remained elusive. In this study, a rationally driven strategy was implemented and applied to engineer myoglobin variants capable of providing access to 1-carboxy-2-aryl-cyclopropanes with high trans-(1R,2R) selectivity and catalytic activity. The stereoselectivity of these cyclopropanation biocatalysts complements that of trans-(1S,2S)-selective variants developed here and previously. In combination with whole-cell biotransformations, these stereocomplementary biocatalysts enabled the multigram synthesis of the chiral cyclopropane core of four drugs (Tranylcypromine, Tasimelteon, Ticagrelor, and a TRPV1 inhibitor) in high yield and with excellent diastereo- and enantioselectivity (98–99.9% de; 96–99.9% ee). These biocatalytic strategies outperform currently available methods to produce these drugs.

Discovery of New Potential Anti-Infective Compounds Based on Carbonic Anhydrase Inhibitors by Rational Target-Focused Repurposing Approaches

In academia, compound recycling represents an alternative drug discovery strategy to identify new pharmaceutical targets from a library of chemical compounds available in house. Herein we report the application of a rational target-based drug-repurposing approach to find diverse applications for our in-house collection of compounds. The carbonic anhydrase (CA, EC 4.2.1.1) metalloenzyme superfamily was identified as a potential target of our compounds. The combination of a thoroughly validated docking screening protocol, together with in vitro assays against various CA families and isoforms, allowed us to identify two unprecedented chemotypes as CA inhibitors. The identified compounds have the capacity to preferentially bind pathogenic (bacterial/protozoan) CAs over human isoforms and represent excellent hits for further optimization in hit-to-lead campaigns.