122676-92-0

Usage

Uses

Used in Organic Chemistry:
(cis)2-Iodocyclopropanecarboxylic acid is used as a reagent for various organic synthesis processes due to its unique cyclopropane structure and iodine atom, which can participate in a range of chemical reactions.
Used in Pharmaceutical Industry:
(cis)2-Iodocyclopropanecarboxylic acid is used as an intermediate in the synthesis of pharmaceutical compounds, leveraging its iodinated carboxylic acid functionality to create novel drug molecules with potential therapeutic applications.

Upstream product

• 467426-68-2 (±)-(cis)-2-iodocyclopropyl-N,N-diethylcarboxamide 
• 122676-91-9 4,5-Methano-1-hydroxyiodoxol-3(1H)-one 
• 122676-95-3 cis-1-(Hydroxymethyl)-2-iodocyclopropane 

Downstream Products

• 692288-05-4 (1S,2S)-2-iodocyclopropanecarboxylic acid 
• 692288-05-4 (1R,2R)-2-iodocyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Total Synthesis of Cardiolipins Containing Chiral Cyclopropane Fatty Acids

Cardiolipin (CL) is a phospholipid located in both the eukaryotic mitochondrial inner membrane and the bacterial cell membrane. Some bacterial CLs are known to contain cyclopropane moieties in their acyl chains. Although the CLs are thought to be involved in the innate immune response, there have been few attempts at chemical synthesis of the CLs, and detailed studies of their biological activities are scarce. Thus, we have developed a synthetic route to CLs containing chiral cyclopropane moieties.

Process development on an efficient new convergent formal synthesis of MIV-150

Starting from a known linear route and a proposed convergent route, we have successfully developed a new hybrid convergent route to MIV-150 that takes advantage of the robust chemistry for the preparation of a fluoroketal and the stereospecific Negishi coupling of an iodocyclopropane moiety to a benzene ring. Stereoselective β- and cis-iodination chemistry was developed for the preparation of an enantiomerically pure iodocyclopropanecarboxylate. Following the Negishi coupling, proven chemistry from the linear route was incorporated, thus ensuring a similar high-purity profile for the final active pharmaceutical ingredient (API). In addition, we have prepared and evaluated a series of basic inorganic and organic MIV-150 salts that have drastically increased water solubility over the parent compound.

Synthesis and Properties of the Valence Tautomer of cis-Iodosocyclopropanecarboxylic Acid: 4,5-Methano-1-hydroxyiodoxol-3(1H)-one

4,5-Methano-1-hydroxyiodoxol-3(1H)-one (4) was synthesized from propionic acid in six steps.Key reactions included Simmons-Smith cyclopropanation of cis-3-iodopropen-2-ol, followed by pyridinium dichromate oxidation to cis-iodocyclopropanecarboxylic acid.The final iodo to iodoso oxidation used either chlorination/hydrolysis or peracetic acid procedures.Compound 4 exists in the 1-hydroxyiodoxolone form, not in the "open" cis-cyclopropanecarboxylic acid form (3), as shown by its "high" pKa (7.55) and by its ability to cleave p-(nitrophenyl)diphenyl phosphate(k = 0.0044 s-1) in pH 8 aqueous micellar solution.Compound 4 disproportionates to iodo (5) and iodoxy (7) compounds in pH 8 aqueous buffer with k = 0.027 L/(M*s).Ab initio molecular orbital calculations are described which help rationalize the observed properties of 4.The reactivity of 4 (and related species) is intimately connected to the structure and bonding around the formally hypervalent iodine atom.