92344-71-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity make it a valuable component in the creation of new drugs and medicinal compounds.
Used in Organic Compounds Synthesis:
(-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid serves as a building block in the synthesis of a range of organic compounds, contributing to the development of new chemical entities with potential applications across different industries.
Used in Material Development:
(-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid may be employed in the development of new materials, leveraging its chemical properties to create innovative products with enhanced performance characteristics.
Used in Chemical Process Innovation:
(-)-(1R,6R)-6-methyl-3-cyclohexenecarboxylic acid could be instrumental in the innovation of chemical processes, potentially improving efficiency, sustainability, or the production of novel chemical intermediates and end products.

Upstream product

• 92344-77-9 1R,6R-(+)-6-Methyl-3-cyclohexenyl-methanol 
• 287178-29-4 (4R)-3-((4'R,5'R)-cyclohexene-4'-carbonyl)-4-(phenylmethyl)-2-oxazolidinone 
• 606933-61-3 (-)-N-[(1'R,6'R)-6-methyl-3-cyclohexenylcarbonyl]bornane-10,2-sultam 
• 92284-47-4 (1R,6R)-6-Methyl-cyclohex-3-enecarboxylic acid ((R)-1-phenyl-ethyl)-amide 
• 92284-49-6 (1R,6R)-6-Methyl-cyclohex-3-enecarboxylic acid (2-hydroxy-ethyl)-((R)-1-phenyl-ethyl)-amide 
• 92284-53-2 (1R,6R)-6-Methyl-cyclohex-3-enecarboxylic acid 2-((R)-1-phenyl-ethylamino)-ethyl ester 
• 107-93-7 (E)-but-2-enoic acid 
• 106-99-0 buta-1,3-diene 
• 89-94-1 trans-6-methyl-3-cyclohexene-1-carboxaldehyde 
• 92284-36-1 (1S,6S)-6-Methyl-cyclohex-3-enecarbonyl chloride 

Downstream Products

• 7076-91-7 (+-)-cis-2-methyl-cyclohexanecarboxylic acid 
• 93296-90-3 (+/-)-cis-6-methyl-cyclohex-3-enecarboxylic acid amide 
• 2425-20-9 optically inactive cis-6-methyl-cyclohex-3-enecarboxylic acid sec-butyl ester 
• 2425-23-2 trans-6-methyl-1-ethoxycarbonyl-3-cyclohexene 
• 15177-62-5 trans-2-methylcyclohexanecarboxylic acid 
• 15111-54-3 (+/-)-cis-1-carbomethoxy-2-methyl-4-cyclohexene 
• 7132-88-9 (+/-)-trans-2-methyl-cyclohexanecarboxylic acid amide 
• 99805-92-2 trans-o-4-menthen-8-ol 
• 6070-02-6 trans-o-menthane 
• 5748-20-9 trimedlure-B1 
• 15111-54-3 methyl trans-6-methyl-3-cyclohexene carboxylate 
• 287178-38-5 ethyl (1R,2R,5S)-5-hydroxy-2-methyl-1-carboxylate 
• 287178-33-0 ethyl (1R,2R,5R)-5-hydroxy-2-methyl-1-carboxylate 
• 287178-36-3 ethyl (1R,2R)-2-methyl-5-one-1-carboxylate 

Relevant academic research and scientific papers

An improved synthesis of ethyl cis-5-iodo-trans-2-methylcyclohexanecarboxylate, a potent attractant for the Mediterranean fruit fly

Both racemic ethyl 5-iodo-2-methylcyclohexanecarboxylate (1), known as Mediterranean fruit fly attractant ceralure B1, and its (-)-(1R,2R,5R) enantiomer 1a were conveniently synthesized from commercially available racemic trans-6-methyl-3-cyclohexenecarboxylic acid 2 or its (1R,6R) enantiomer 2a. Key steps included an asymmetric Diels-Alder reaction using a sultam auxiliary and cyclization of the unwanted trans-5-iodo-trans-2-methylcyclohexanecarboxylic acid (8) to the intermediate lactone 7 (or 8a to 7a). The new method may circumvent chromatographic separations and seems amenable to scale-up.

Attractant for the mediterranean fruit fly, the method of preparation and method of use

A method of attracting the Mediterranean fruit fly by subjecting the Mediterranean fruit fly to an attractant, wherein the attractant is ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate in an enantomeric excess of at least 70% and a regio- and diastereochemical purity of >5:1. The compound ethyl (1R,2R,5R)-5-iodo-2-methylcyclohexane-1-carboxylate, in an enantomeric excess of at least 70% and a regio- and diastereochemical purity of >5:1, may be stereoselectively synthesized on a multigram scale in 15% yield by reacting ethyl (1R,2R,5S)-5-hydroxy-2-methyl-1-carboxylate with Ph3P-imidazole-I2(or Ph3P-2,6-lutidine-I2) in a carbon tetrachloride/methlylene chloride mixture. The 1R,2R,5R enantiomer is significantly more attractive than its enantiomeric counterpart (1S,2S,5S), or either of the commercial products trimedlure or ceralure, each a mixture of 16 regio and stereoisomers.

Enantioselective synthesis of ceralure B1, ethyl cis-5-iodo-trans-2- methylcyclohexane-1-carboxylate

Ethyl (1R, 2R, 5R)-5-iodo-2-methylcyclohexane-1-carboxylate is a potent attractant for the Mediterranean fruit fly. This compound was stereoselectively synthesized on a multigram scale in nine steps in 15% yield. Key steps of the synthesis involved an asymmetric Diels-Alder reaction, iodolactonization, stereoselective reduction of the carbonyl, and inversion of configuration with iodide. (C) 2000 Elsevier Science Ltd.

STUDIES OF COMPOUNDS IN THE MENTHANE SERIES. XIX. SYNTHESIS AND PROPERTIES OF TRANS-o-4-MENTHEN-8-OL AND STEREOISOMERIC o-5-METHEN-8-OLS

Trans-o-4-Menthen-8-ol and cis- and trans-o-5-menthen-8-ols have been prepared via the Diels-Alder reactions of 1,3-butadiene with crotonaldehyde in the presence of boron trifluoride etherate, and piperylene with methyl acrylate, respectively.The dehydration reactions of these alcohols have been studied in the presence of acetic anhydride and potassium bisulfate; the latter reagent demonstrates a high reaction selectivity.

Enantiomers of the Biologically Active Components of the Insect Attractant Trimedlure

The biologically most active components of a synthetic lure that is used to attract male Mediterranean fruit flies are the tert.-butyl esters of cis-4-(and trans-5-)chloro-trans-2-methylcyclohexanecarboxylic acids (1-A and 1-C).These compounds have been s