105393-23-5

Basic information

• Product Name: 2-(4-tert-butylphenyl)cyclopropane-1-carboxylic acid ethyl ester
• Synonyms: 2-(4-tert-butylphenyl)cyclopropane-1-carboxylic acid ethyl ester
• CAS NO: 105393-23-5
• Molecular Weight: 246.349
• Mol File: 105393-23-5.mol
• Article Data: 34

Chemical Properties

• CAS DataBase Reference: 2-(4-tert-butylphenyl)cyclopropane-1-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-tert-butylphenyl)cyclopropane-1-carboxylic acid ethyl ester(105393-23-5)
• EPA Substance Registry System: 2-(4-tert-butylphenyl)cyclopropane-1-carboxylic acid ethyl ester(105393-23-5)

Safety Data

• Hazardous Substances Data: 105393-23-5(Hazardous Substances Data)

Usage

Ester derivative

Cyclopropane carboxylic acid This compound is an ester derivative of cyclopropane carboxylic acid, which means it has an ester functional group (-COO-) formed by the reaction of a carboxylic acid with an alcohol.

tert-Butylphenyl group

Attached to the cyclopropane ring The tert-butylphenyl group is a substituent attached to the cyclopropane ring, which consists of a phenyl ring (a six-membered aromatic ring) with a tert-butyl group (a bulky, three-methyl group) attached to it.

Common uses

Organic synthesis and pharmaceutical research This compound is frequently used in the synthesis of other organic compounds and as a starting material in pharmaceutical research due to its unique structure and reactivity.

Potential biological activities

Pharmacological properties 2-(4-tert-butylphenyl)cyclopropane-1-carboxylic acid ethyl ester has shown potential for biological activities and pharmacological properties, making it a promising candidate for further study and potential drug development.

Unique structure

Interesting target for study The compound's unique structure, with the tert-butylphenyl group attached to the cyclopropane ring, makes it an interesting target for further research and investigation in the field of chemistry and pharmacology.

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 1746-23-2 4-tert-Butylstyrene 
• 623-33-6 glycine ethyl ester hydrochloride 
• 82665-91-6 α,α-diiodoethylacetate 
• 186581-53-3 diazomethane 
• 158010-17-4 ethyl (E)-3-[4-(tert-butylphenyl)]-2-propenoate 
• 75237-09-1 ethyl 4-(4-(tert-butyl)phenyl)-4-oxobutanoate 
• 115199-52-5 ethyl 4-(p-t-butylphenyl)-4-hydroxybutanoate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 140-88-5 ethyl acrylate 

Downstream Products

• 438616-66-1 2-(4-tert-butylphenyl)cyclopropanecarbohydrazide 
• 445029-32-3 2-[4-(tert-butyl)phenyl]cyclopropanecarboxylic acid 
• 105393-24-6 2-[4-(tert-butyl)phenyl]cyclopropylmethanol 
• 134030-39-0 ethyl 4-(4-(tert-butyl)phenyl)butanoate 

Relevant articles and documents

Cyclopropanation of activated olefins catalysed by Ru-phosphine complexes

Two novel ruthenium complexes, RuH3[Si(OEt)3](PPh3)2 and Ru[Si(OEt)3]2(PPh3)2, have been shown to catalyse the cyclopropanation of activated olefins in high yields.

Two-step synthesis of trans-2-arylcyclopropane carboxylates with 98-100% ee by the use of a phosphazene base

Only the axial diastereomer of sulfonium salts 2 are formed upon alkylation of 1. Deprotonation of 2 results in ylides, which allow the highly enantioselective cyclopropanation of Michael systems. The chirat auxiliary 1 is recovered and can be reused.

Cyclopropanation reactions catalysed by rhodium(I) complexes with new anionic carborane phosphine ligands

The first set of rhodium(I) complexes 1-3 has been shown to be active for the cyclopropanation of olefins with diazoaeetates.

Platinum-catalysed cyclopropanation of olefins with ethyl diazoacetate

The addition of ethyl diazoacetate to olefins in the presence of a catalytic amount of platinum complexes provides the corresponding cyclopropanes in good to excellent yields.

Tuning Rh(ii)-catalysed cyclopropanation with tethered thioether ligands

Dirhodium(ii) paddlewheel complexes have high utility in diazo-mediated cyclopropanation reactions and ethyl diazoacetate is one of the most commonly used diazo compounds in this reaction. In this study, we report our efforts to use tethered thioether ligands to tune the reactivity of RhII-carbene mediated cyclopropanation of olefins with ethyl diazoacetate. Microwave methods enabled the synthesis of a family of RhII complexes in which tethered thioether moieties were coordinated to axial sites of the complex. Different tether lengths and thioether substituents were screened to optimise cyclopropane yields and minimise side product formation. Furthermore, good yields were obtained when equimolar diazo and olefin were used. Structural and spectroscopic investigation revealed that tethered thioethers changed the electronic structure of the rhodium core, which was instrumental in the performance of the catalysts. Computational modelling of the catalysts provided further support that the tethered thioethers were responsible for increased yields. This journal is

Ruthenium-arene catalysts bearing N-heterocyclic carbene ligands for olefin cyclopropanation and metathesis

Ruthenium-arene complexes bearing N-heterocyclic carbene (NHC) ligands with the generic formula [RuCl2(p-cymene)(NHC)] are efficient catalyst precursors for the cyclopropanation of activated olefins with ethyl diazoacetate, and the cis/trans di

EFFECTS OF SECONDARY INTERACTIONS ON THE STEREOCHEMICAL OUTCOME OF RHODIUM(II) CARBOXYLATE-CATALYSED CYCLOPROPANATION OF OLEFINS

In cyclopropanation reactions of olefins catalysed by various dirhodium(II) tetracarboxylates, it is shown that besides the wellrecognized electronic and steric effects, secondary interactions between the carbenoid complex and the substrate largely determ

First example of supported microwave-assisted synthesis of new chiral bipyridines and a terpyridine - Use in asymmetric cyclopropanation

We present herein the first alumina-supported synthesis of chiral bipyridines and of a chiral C2-symmetric terpyridine conducted under microwave irradiation, and our preliminary results from copper-mediated enantioselective cyclopropanation with this terpyridine. Reaction yields were excellent and enantioselectivities of up to 87percent were observed. Moreover, with trans-β-methylstyrene, a remarkable diastereoselectivity (ratio trans/cis = 7:93) was observed.

Selective carbene transfer to amines and olefins catalyzed by ruthenium phthalocyanine complexes with donor substituents

Electron-rich ruthenium phthalocyanine complexes were evaluated in carbene transfer reactions from ethyl diazoacetate (EDA) to aromatic and aliphatic olefins as well as to a wide range of aromatic, heterocyclic and aliphatic amines for the first time. It was revealed that the ruthenium octabutoxyphthalocyanine carbonyl complex [(BuO)8Pc]Ru(CO) is the most efficient catalyst converting electron-rich and electron-poor aromatic olefins to cyclopropane derivatives with high yields (typically 80-100%) and high TON (up to 1000) under low catalyst loading and nearly equimolar substrate/EDA ratio. This catalyst shows a rare efficiency in the carbene insertion into amine N-H bonds. Using a 0.05 mol% catalyst loading, a high amine concentration (1 M) and 1.1 eq. of EDA, a number of structurally divergent amines were selectively converted to mono-substituted glycine derivatives with up to quantitative yields and turnover numbers reaching 2000. High selectivity, large substrate scope, low catalyst loading and practical reaction conditions place [(BuO)8Pc]Ru(CO) among the most efficient catalysts for the carbene insertion into amines.

A transition-metal-free & diazo-free styrene cyclopropanation

An operationally simple and broadly applicable novel cyclopropanation of styrenes using gem-diiodomethyl carbonyl reagents has been developed. Visible-light triggered the photoinduced generation of iodomethyl carbonyl radicals, able to cyclopropanate a wide array of styrenes with excellent chemoselectivity and functional group tolerance. To highlight the utility of our photocyclopropanation, we demonstrated the late-stage functionalization of biomolecule derivatives.