439924-29-5

Usage

Uses

Used in Organic Synthesis:
Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)(9CI) is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure and functional groups make it a versatile building block for the synthesis of a wide range of compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)(9CI) is employed as a starting material for the synthesis of bioactive molecules and compounds with potential medicinal properties. Its specific stereochemistry and functional groups enable the development of chiral drugs with improved efficacy and selectivity.
Used in Agrochemicals:
Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)(9CI) may also find applications in the agrochemical sector, where it can be used as a precursor for the synthesis of agrochemicals such as pesticides and herbicides. Its unique structure and functional groups can contribute to the development of novel and effective agrochemicals.
Used in Material Science:
In the field of material science, Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)(9CI) can be utilized for the development of new materials with specific properties. Its functional groups and stereochemistry can be exploited to create materials with tailored characteristics for various applications, such as polymers, coatings, and adhesives.

Upstream product

• 2216-51-5 (-)-menthol 
• 773837-37-9 sodium cyanide 
• 2230-82-2 menthyl tosylate 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 142921-58-2 (1S,2R,5S)-(+)-menthol Mesylate 
• 61548-81-0 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate 
• 28953-96-0 2-chloro-1-isopropyl-4-methyl-cyclohexane 
• 151-50-8 potassium cyanide 
• 143-33-9 sodium cyanide 

Downstream Products

• 180729-58-2 (+)-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl](2'-pyridyl)ketone 
• 70985-58-9 (1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid 
• 1207722-22-2 (1S,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanecarbonyl Chloride 
• 16052-40-7 (-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid 
• 1845-44-9 (1R,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carboxaldehyde 
• 485843-44-5 (1S,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carboxaldehyde 
• 62309-29-9 (1S,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid 
• 108235-79-6 (1S,2R,5S)-2-isopropyl-5-methylcyclohexane-1-carbonyl chloride 

Relevant academic research and scientific papers

Synthesis, characterization and hplc analysis of the (1S,2S,5R)-diastereomer and the enantiomer of the clinical candidate ar-15512

AR-15512 (formerly known as AVX-012 and WS-12) is a TRPM8 receptor agonist currently in phase 2b clinical trials for the treatment of dry eye. This bioactive compound with menthol-like cooling activity has three stereogenic centers, and its final structure and absolute configuration, (1R,2S,5R), have been previously solved by cryo-electron microscopy. The route of synthesis of AR-15512 has also been reported, revealing that epimerization processes at the C-1 can occur at specific stages of the synthesis. In order to confirm that the desired configuration of AR-15512 does not change throughout the process and to discard the presence of the enantiomer in the final product due to possible contamination of the initial starting material, both the enantiomer of AR-15512 and the diastereomer at the C-1 were synthesized and fully characterized. In addition, the absolute configuration of the (1S,2S,5R)-diastereomer was determined by X-ray crystallographic analysis, and new HPLC methods were designed and developed for the identification of the two stereoisomers and their comparison with the clinical candidate AR-15512.

Method for preparing menthol carboxamide intermediate peppermint acid

The invention discloses a method for preparing a menthol carboxamide intermediate peppermint acid. The method takes L-menthol as a starting raw material and comprises the following steps: enabling theL-menthol and p-toluene sulfonyl chloride to react to obtain menthyl toluenesulfinate; then enabling the menthyl toluenesulfinate to react with sodium cyanide to obtain cyano-peppermint; finally, hydrolyzing to obtain the peppermint acid. The synthesis method disclosed by the invention is simple and is suitable for industrial production; meanwhile, a lot of difficult-to-treat wastewater is avoided. The obtained peppermint acid has a good crystal form; the purity is greater than or equal to 97 percent, the yield is greater than or equal to 85 percent and ee is greater than or equal to 99.0 percent.

Triiodide-Mediated δ-Amination of Secondary C?H Bonds

The Cδ?H amination of unactivated, secondary C?H bonds to form a broad range of functionalized pyrrolidines has been developed by a triiodide (I3?)-mediated strategy. By in situ 1) oxidation of sodium iodide and 2) sequestration of the transiently generated iodine (I2) as I3?, this approach precludes undesired I2-mediated decomposition which can otherwise limit synthetic utility to only weak C(sp3)?H bonds. The mechanism of this triiodide-mediated cyclization of unbiased, secondary C(sp3)?H bonds, by either thermal or photolytic initiation, is supported by NMR and UV/Vis data, as well as intercepted intermediates.

SYNTHESIS OF CYCLOHEXANE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS

The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

Novel 2-(hydroxyalkyl)pyridines derived from the chiral pool

Two diastereomeric 2-(1-hydroxyalkyl)pyridines were conveniently prepared starting from (-)-menthol. The pyridylalcohols were subsequently allowed to react with phosphorus oxychloride to yield, in one step, C3-symmetric tripodal tripyridine lig