64326-19-8

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)-1-methyl-2-cyclohexene-1-carboxylic acid is used as a building block for the synthesis of various drugs and pharmaceutical compounds due to its unique structure and functional groups.
Used in Organic Chemistry:
(+/-)-1-methyl-2-cyclohexene-1-carboxylic acid is used as a reagent for the preparation of other organic molecules, contributing to the development of new chemical entities and compounds.

Upstream product

• 62115-15-5 cyclohex-2-ene-1-carboxylic acid 
• 74-88-4 methyl iodide 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 69216-87-1 2-Mesyloxy-1-methyl-1-aethoxycarbonyl-cyclohexan 
• 66088-42-4 ethyl 1-methyl-2-hydroxycyclohexanecarboxylate 
• 66088-37-7 ethyl 1-methyl-2-oxocyclohexancarboxylate 
• 49768-04-9 1-Methyl-cyclohexen-⁽²⁾-carbonsaeure-aethylester 

Downstream Products

• 1123-25-7 1-methyl-1-cyclohexanecarboxylic acid 
• 1315320-24-1 C₁₄H₁₇NO₂ 
• 343269-60-3 1-methyl-2-cyclohexene-1-carbonyl chloride 

Relevant academic research and scientific papers

Tandem Decarboxylative Cyclization/Alkenylation Strategy for Total Syntheses of (+)-Longirabdiol, (-)-Longirabdolactone, and (-)-Effusin

Structurally complex and bioactive ent-kaurane diterpenoids have well-characterized biological functions and have drawn widespread attention from chemists for many decades. However, construction of highly oxidized forms of such diterpenoids still presents considerable challenges to synthetic chemists. Herein, we report the first total syntheses of C19 oxygenated spiro-lactone ent-kauranoids, including longirabdiol, longirabdolactone, and effusin. A concise synthesis of the common intermediate used for all three syntheses was enabled via three free-radical-based reactions: (1) a newly devised tandem decarboxylative cyclization/alkenylation sequence that forges the cis-19, 6-lactone concomitantly with vicinal alkenylation, (2) a Ni-catalyzed decarboxylative Giese reaction that constructs C10 quaternary center stereoselectively, and (3) a vinyl radical cyclization that generates a rigid bicyclo[3.2.1]octane. A series of late-stage oxidations from the common intermediate then provided each of the natural products in turn. Further biological evaluation of these synthetic natural products reveals broad anticancer activities.

Metal-free oxyaminations of alkenes using hydroxamic acids

A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.