277756-46-4 | 1-(Trifluoromethyl)cyclopropane-1-carboxylic acid

CAS:277756-46-4 | 1-(Trifluoromethyl)cyclopropane-1-carboxylic acid ,Description

1-(Trifluoromethyl)cyclopropane-1-carboxylic acid (TFMCCA) is a synthetic compound that has been used in a variety of scientific research applications. It is a cyclic monocarboxylic acid that has a trifluoromethyl substituent at the 1-position. TFMCCA has been studied for its potential use in drug discovery, as well as for its biochemical and physiological effects. 
 

Scientific Research Applications

Metabolite Identification in Plants1-(Trifluoromethyl)cyclopropane-1-carboxylic acid, as part of the 1-aminocyclopropane-1-carboxylic acid (ACC) family, shows significant relevance in plant biology. For example, Hoffman, Yang, and McKeon (1982) identified 1-(malonylamino)cyclopropane-1-carboxylic acid as a major conjugate of ACC, an ethylene precursor in higher plants. This discovery provides insights into the metabolic pathways of cyclopropane carboxylic acid derivatives in plants (Hoffman, Yang, & McKeon, 1982).

Synthesis and Ring Cleavage ReactionsIn organic synthesis, the conversion of carboxylic esters into fluorinated ketones via ring cleavage of cyclopropanol intermediates has been explored. Konik et al. (2017) demonstrated the use of cyclopropane ring cleavage reactions to synthesize β-trifluoromethyl ketones, highlighting the utility of 1-(trifluoromethyl)cyclopropane-1-carboxylic acid derivatives in generating reactive trifluoromethyl copper species (Konik et al., 2017).

Diastereoselective Ring OpeningZ. Hell et al. (2000) investigated the reaction of cyclopropane carboxylic acid derivatives with sulfur tetrafluoride, demonstrating diastereoselective ring opening. This process allows for the conversion of these derivatives into trifluoromethyl group-containing compounds, showing potential in stereochemical applications (Hell et al., 2000).

Enantioselective SynthesisDenton, Sukumaran, and Davies (2007) showcased the enantioselective synthesis of trifluoromethyl-substituted cyclopropanes, a category that includes 1-(trifluoromethyl)cyclopropane-1-carboxylic acid. This synthesis utilized adamantylglycine-derived dirhodium complexes, indicating its potential in creating highly selective and stereochemically controlled compounds (Denton, Sukumaran, & Davies, 2007).

Cyclopropane Building Blocks in Drug DiscoveryThe synthesis and applications of fluorinated cyclopropane derivatives have also been explored in the context of drug discovery. Thomson et al. (2018) reported on the synthesis of aryl α,β,β-trifluorocyclopropanes and their potential as novel motifs in this field, due to their lipophilicity and structural uniqueness (Thomson et al., 2018).

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