52920-02-2

Usage

Uses

Used in Organic Synthesis:
(1R,2R)-rel-2-(Methoxycarbonyl)cyclopropanecarboxylic acid serves as a valuable intermediate in organic synthesis, providing a cyclopropane ring and carboxylic acid functionality that can be further elaborated upon to create a variety of complex organic molecules.
Used in Pharmaceutical Research:
As a chiral molecule, (1R,2R)-rel-2-(Methoxycarbonyl)cyclopropanecarboxylic acid is utilized in pharmaceutical research for the development of enantiomerically pure compounds. Its unique stereochemistry and functional groups can contribute to the design of novel drugs with improved efficacy and selectivity.
Used as a Building Block for Complex Molecule Synthesis:
The presence of the cyclopropane ring in (1R,2R)-rel-2-(Methoxycarbonyl)cyclopropanecarboxylic acid endows it with unique properties that can be harnessed in the synthesis of complex molecules. It can be used as a building block to construct intricate molecular architectures with potential applications in various fields, including materials science and medicinal chemistry.
Used in Chemical and Biological Applications:
The cyclopropane ring in (1R,2R)-rel-2-(Methoxycarbonyl)cyclopropanecarboxylic acid may impart distinctive properties that are beneficial for chemical and biological applications. Its unique structure can be exploited to develop new reagents, catalysts, or probes for studying biological systems and chemical processes.

Upstream product

• 5617-74-3 cis-1,2-cyclopropanedicarboxylic acid anhydride 
• 124-41-4 sodium methylate 
• 826-34-6 dimethyl cis-cyclopropane-1,2-dicarboxylate 
• 67-56-1 methanol 
• 5617-74-3 3-oxabicyclo[3.1.0]hexane-2,4-dione 
• 5861-31-4 methyl trans-2-phenylcyclopropanecarboxylate 
• 826-35-7 dimethyl trans-1,2-cyclopropanedicarboxylate 
• 58616-95-8 trans-1,2-cyclopropanedicarboxylic acid 
• 3999-55-1 diethyl trans-cyclopropane-1,2-dicarboxylate 

Downstream Products

• 826-34-6 dimethyl cis-cyclopropane-1,2-dicarboxylate 
• 13279-89-5 (+/-)-trans-2-Carbomethoxycyclopropanecarbonyl-chloride 
• 1520120-90-4 (1S,2S)-2-(benzyloxycarbonyl)cyclopropanecarboxylic acid 
• 1520120-86-8 benzyl (1R,2R)-2-carbamoylcyclopropanecarboxylate 
• 14590-54-6 (1S,2S)-cyclopropane-1,2-dicarboxylic acid 

Relevant academic research and scientific papers

CYCLOPROPANECARBOXYLIC ACID GPR120 MODULATORS

The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are GPR120 G protein coupled receptor modulators which may be used as medicaments

PHENYL-(AZA)CYCLOALKYL CARBOXYLIC ACID GPR120 MODULATORS

The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are GPR120 G protein-coupled receptor modulators which may be used as medicaments.

AROMATIC RING COMPOUND

The present invention provides an aromatic ring compound having a melanin-concentrating hormone receptor antagonistic action and useful as an agent for the prophylaxis or treatment of obesity and the like. The present invention relates to a compound represented by the formula wherein each symbol as defined in the specification, or a salt thereof.

(2R,1'S,2'R)- And (2S,1'S,2'R)-3-[2-mono(di,tri)fluoromethylcyclopropyl] alanines and their incorporation into hormaomycin analogues

Efficient and scalable syntheses of enantiomerically pure (2 R ,1' S ,2' R )- and (2 S ,1' S ,2' R )-3-[2-mono(di,tri)fluoromethylcyclopropyl] alanines 9a - c , as well as allo-D-threonine ( 4 ) and ( 2 S,3R)-β-methylphenylalanine (3), using the Belokon' approach with (S )- and (R )-2-[( N-benzylprolyl)amino]benzophenone [(S)- and (R)-10 ] as reusable chiral auxiliaries have been developed. Three new fluoromethyl analogues of the naturally occurring octadepsipeptide hormaomycin ( 1 ) with (fluoromethylcyclopropyl) alanine moieties have been synthesized and subjected to preliminary tests of their antibiotic activity.

Highly enantioselective desymmetrization of meso anhydrides by a bifunctional thiourea-based organocatalyst at low catalyst loadings and room temperature

(Chemical Equation Presented) Bifunctional (thio)urea-based cinchona alkaloid derivatives have been shown to promote highly efficient enantioselective desymmetrization reactions of meso anhydrides. The most selective of these catalysts is capable of the enantioselective methanolysis of succinic and glutaric anhydride derivatives to form hemiester products with >90% yield and enantiomeric excess at 1 mol % loading and ambient temperature.

Dipolar cycloaddition of carbonyl ylides generated from methyl cis-2-diazoacetyl-1-cyclopropanecarboxylates

Carbonyl ylide generated from methyl cis-3-diazoacetyl-2,2-diphenyl-1- cyclopropanecarboxylate in the presence of Rh2(OAc)4 when brought into reaction of 1,3-dipolar cycloadditionCyrillic small letter YA sign with N-arylmaleimides afforded substituted 4-aryl-7-methoxy-9,9-diphenyl-12-oxa- 4-azatetracyclo-[5.4.1.02,6.08,10]dodecene-3,5,11-triones. Concurrent processes resulted in formation of cycloheptatrienes, hydroxyacetylcyclopropanecarboxylates, and benzophenone. Carbonyl ylide generated from methyl cis-2-diazoacetyl-1-cyclopropanecarboxylate in the same reaction gave rise to exo- and endo-4-aryl-7-methoxy-12-oxa-4-azatetracyclo[5.4. 1.02,6 .08,10] dodecene-3,5,11-triones. 2005 Pleiades Publishing, Inc.

Synthesis and radical polymerization of various 2-cyclopropylacrylates

Fourteen new alkyl 2-cyclopropylacrylates 1a-n with various substituents R1-R5 were synthesized from readily available precursors by applying standard transformations such as cyanohydrin formation from an aldehyde, alcoholysis to an α-hydroxycarboxylic ester, oxidation and Wittig methylenation of an α-oxocarboxylic ester. Overall yields ranged from 33 to 54%. A new method for the hydrolysis of dimethyl cyclopropanedicarboxylates to the corresponding half-esters was developed. The α-oxocarboxylates 7g-n were prepared by dirhodium tetraacetate catalyzed cyclopropanation of alkenes 8g-n with methyl or ethyl diazopyruvate in 32-58% yield. The monomers 1a-n were characterized by 1H, 13C NMR spectroscopy, mass spectrometry and elemental analysis. The radical homopolymerizations of 1a-n were carried out with 2,2′- azabisisobutyronitrile (AIBN) as initiator in chlorobenzene at 65 °C. The highest polymer yields were obtained in the polymerizations of If and 1h or 1k and 11, i.e. from monomers with an annelated five- or six-membered ring. In the case of 1h and 1k, both the polymer yields (99 and 98%, respectively) and the glass transition temperatures (Tg) of 57 and 93 °C were significantly higher than those observed for the polymer from 1,1-bis(ethoxycarbonyl)-2-vinylcyclopropane (DECVCP), which was used as a benchmark for the monomer reactivities in the radical polymerizations of all the vinylcyclopropane derivatives 1a-n. The bicyclic monomers 1h and 1k also demonstrated drastically improved reactivities in the radical copolymerization with methyl methacrylate when compared to DECVCP. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Solid phase synthesis of diamides as potential bone resorption inhibitors

Unsymmetrical diamide libraries have been prepared by a general and versatile solid phase route, using diacid templates in combination with aromatic and aliphatic amines chosen with the help of statistical experimental design. The compounds were tested as

Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: Synthesis and structural study of a conformationally constrained β-dipeptide

Synthetic approaches to carbocyclic compounds, namely cyclopropane and cyclobutane β-amino acids, are presented. One of them is based on enzymatic desymmetrization of meso diesters, leading to the enantioselective production of cis-hemiesters, which afforded β-amino acids through Curtius rearrangements. The enantiomeric excess for the cyclobutane derivatives was 91% whereas the cyclopropanes were obtained in 63% ee. According to another strategy, an enantiomerically pure cyclopropane trans-β-amino acid, bearing a quaternary center, has been synthesized from a homochiral precursor easily available from D-glyceraldehyde. The preparation and structural investigation of the first synthesized cyclobutane containing dipeptide is also described. A hairpin-like conformation of this molecule in the solid state has been demonstrated by X-ray structural analysis, showing crystal packing induced by the presence of the rigid cyclobutane moiety and the formation of intermolecular hydrogen bonds. NMR experiments confirmed that these molecules also tend to produce aggregates in solution. On the contrary, theoretical calculations suggest that intramolecular interactions are important in the gas phase, as expected. Copyright (C) 2000 Elsevier Science Ltd.

ATP-sensitive potassium channel openers: Synthesis and antihypertensive activity of 4-bicycloxybenzopyrans

Synthesis and hypotensive activity of trans-3,4-dihydro-3-hydroxy-4-[(5-oxo-3,4-diazabicyclo[4.1.0]hept-2-en-2 -yl)oxy]-2H-1-benzopyrans and their congeners are described. Compounds (-)-9eB and (-)-20B were highly potent ATP-sensitive potassium channel openers.