439924-29-5

Basic information

• Product Name: Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- (9CI)
• Synonyms: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanecarbonitrile;Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- (9CI);(1R,2S,5R)-(-)-Menthyl cyanide
• CAS NO: 439924-29-5
• Molecular Formula: C11H19N
• Molecular Weight: 165.27526
• Product Categories: ISOPROPYL
• Mol File: 439924-29-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 251.0±9.0 °C(Predicted)
• Appearance: /
• Density: 0.87±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- (9CI)(439924-29-5)
• EPA Substance Registry System: Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- (9CI)(439924-29-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 439924-29-5(Hazardous Substances Data)

Usage

General Description

Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- (9CI) is a chemical compound with a molecular formula C11H19N. It is a derivative of cyclohexanecarbonitrile with a methyl and isopropyl functional group attached to the second and fifth carbon atoms, respectively. Cyclohexanecarbonitrile, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- (9CI) is stereochemically defined as having a 1R, 2S, and 5R configuration. It is commonly used in organic synthesis and pharmaceutical research as a building block for the synthesis of various bioactive molecules and compounds with potential medicinal properties. Additionally, it may also have applications in the field of agrochemicals and material science.

Upstream product

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

Downstream Products

• 16052-40-7 (-)-(1R,3R,4S)-4-isopropyl-1-methylcyclohexane-3-carboxylic acid 
• 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 
• 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 
• 180729-58-2 (+)-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl](2'-pyridyl)ketone 

Relevant articles and documents

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.

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.

Syntheses of c-l axial derivatives of l-menthol

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