499-02-5

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYLENECYCLOPROPANE-TRANS-1,2-DICARBOXYLIC ACID is used as a key intermediate for the synthesis of various antibacterial and antifungal agents. Its application is particularly focused on the regioselective green preparation of (arylnitroethyl)indoles and (arylnitroethyl)pyrroles, which exhibit potent bioactivity against a range of bacterial and fungal pathogens.
3-METHYLENECYCLOPROPANE-TRANS-1,2-DICARBOXYLIC ACID plays a crucial role in the Michael addition of indole and pyrrole to trans-β-nitroolefins, a process catalyzed by hydrogen bond donor Feist's catalyst. This reaction pathway allows for the efficient and environmentally friendly production of biologically active molecules, contributing to the development of novel therapeutic agents in the pharmaceutical industry.

InChI:InChI=1/C6H6O4/c1-2-3(5(7)8)4(2)6(9)10/h3-4H,1H2,(H,7,8)(H,9,10)/p-2/t3-,4-/m1/s1

Upstream product

• 18152-79-9 ethyl 3-bromo-4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate 
• 141-97-9 ethyl acetoacetate 
• 3385-34-0 ethyl isodehydroacetate 
• 148152-70-9 (1S,2S)-(-)-3-methylenecyclopropane-1,2-dicarboxylic acid (R)-(+)-α-methylbenzammonium salt 
• 148082-88-6 (1R,2R)-(+)-3-methylenecyclopropane-1,2-dicarboxylic acid (R)-(+)-α-methylbenzammonium salt 

Downstream Products

• 1391950-67-6 (1R,2R)-N₁,N₂-benzyl-3-methylenecyclopropane-1,2-dicarboxamide 
• 499-02-5 (1R,2R)-(+)-3-methylenecyclopropane-1,2-dicarboxylic acid 
• 499-02-5 (1S,2S)-3-methylene-cyclopropane-1,2-dicarboxylic acid 
• 123-76-2 levulinic acid 
• 148152-70-9 (1S,2S)-(-)-3-methylenecyclopropane-1,2-dicarboxylic acid (R)-(+)-α-methylbenzammonium salt 
• 148082-88-6 (1R,2R)-(+)-3-methylenecyclopropane-1,2-dicarboxylic acid (R)-(+)-α-methylbenzammonium salt 
• 1391950-71-2 (1S,2S)-N₁,N₂-benzyl-3-methylenecyclopropane-1,2-dicarboxamide 
• 107520-09-2 (+/-)-methylene-cyclopropane-1r,2t-dicarboxylic acid-dianilide 
• 95898-34-3 (+)-trans-methylenecyclopropane-2,3-dicarboxamide 
• 134716-70-4 [(2S,3S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopropyl]-carbamic acid benzyl ester 
• 39653-07-1 (+/-)-methylene-cyclopropane-1r,2t-dicarbonyl chloride 
• 263169-44-4 (2S,2'R,3'R)-N-[(R)-α-phenylglycinyl]-2-(1'-[3H]-2',3'-dicarbomethoxycyclopropyl)glycinonitrile 
• 127696-06-4 (2S-trans)-2,3-bis[(t-butyldiphenylsilyloxy)methyl]-cyclobutanone 
• 132164-71-7 C₃₈H₄₆O₂Si₂ 

Relevant academic research and scientific papers

Synthesis of some C2-symmetric bidentate ligands and their complexes derived from Feist's acid

Various new C2-symmetric bidentate ligands, bearing phosphorus, nitrogen, and sulfur, were obtained in an efficient manner, starting from (±)-trans-3-methylidenecyclopropane-1,2-dicarboxylic acid (Feist's acid; (±)-trans-3). The structures of the new bidentate ligands, di(tert-butyl) (±)-[(trans-3-methylidenecyclopropane-1,2-diyl)dimethanediyl] biscarbamate ((±)-9), (±)-(trans-3-methyldienecyclopropane-1,2- diyl)dimethanaminium dichloride ((±)-10), (±)-S,S′-[(trans- 3-methylidenecyclopropane-1,2-diyl)dimethanediyl] diethanethioate ((±)-11), and (±)-[(trans-3-methylidenecyclopropane-1,2-diyl) dimethanediyl]bis(diphenylphosphane) ((±)-12), were fully characterized by standard spectroscopic techniques. These new classes of C2- symmetric bidentate ligands have the potential to be used in asymmetric catalysis. Copyright

Synthesis and characterization of some new c2 symmetric chiral bisamide ligands derived from chiral feist's acid

The hemilabile chiral C2 symmetrical bidentate substituted amide ligands (1R,2R)-5a-d and (1S,2S)-6a-d were synthesized in quantitative yield from (1R,2R)-(+)-3- methylenecyclo-propane-1,2-dicarboxylic acid (1R,2R)-3 and (1S,2S)-(-)-3-methylenecyclopropane- 1,2-dicarboxylic acid (1S,2S)-3, in two steps, respectively. The chiral Feist's acids (1R,2R)-3 and (1S,2S)-3 were obtained in good isomeric purity by resolution of trans-(±)-3-methylene-cyclopropane-1,2-dicarboxylic acid from an 8:2 mixture of tert-butanol and water, using (R)-(+)-α-methylbenzyl amine as a chiral reagent. This process is reproducible on a large scale. All these new synthesized chiral ligands were characterized by 1H-NMR, 13C-NMR, IR, and mass spectrometry, as well as elemental analysis and their specific rotations were measured. These new classes of C2 symmetric chiral bisamide ligands could be of special interest in asymmetric transformations.

C2-Symmetric Ligands for Asymmetric Catalysis based on Feist's Acid

(2R,3R)-(+)-Feist's acid has been converted via its dimethyl ester into (2R,3R)-(-bis(diphenylmethanol)-1-methylenecyclopropane, the corresponding bisdiol and bismesylate derivatives, and the racemic analogues of these derivatives has been converted into the bisazide, bis amino compounds and a bisindenyl derivative in good yields.

Process for the preparation of an antiviral agent

Racemic Feist's acid is treated with (R)-(+)-α-methylbenzylamine to yield (1R-trans)-3-methylenecyclopropane-1,2-dicarboxylic acid, (R)-α-methylbenzylamine (1:1) salt. This salt can then be converted to (1R-trans)-3-methylene-1,2-cyclopropanedicarboxylic acid, dimethyl ester which is an intermediate in the preparation of the antiviral agent [1R-(1α,2β, 3α)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-1,9-dihydro-6H-purin-6-one. The improved process also enables the recovery of racemic Feist's acid from the resolution.