16052-40-7

Basic information

• Product Name: [1R-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexanecarboxylic acid
• Synonyms: [1R-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexanecarboxylic acid;(1R)-5β-Methyl-2α-(1-methylethyl)-1β-cyclohexanecarboxylic acid;Cyclohexanecarboxylic acid, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-;Einecs 240-199-3;(1R,2S,5R)-5-Methyl-2-isopropylcyclohexanecarboxylic acid;(1R,3R,4S)-p-Menthane-3-carboxylic acid;(1R,2S,5R)-2-isopropyl-5-Methylcyclohexanecarboxylic acid;(-)-Menthylformic acid
• CAS NO: 16052-40-7
• Molecular Formula: C₁₁H₂₀O₂
• Molecular Weight: 184.2753
• EINECS: 240-199-3
• Mol File: 16052-40-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 271℃
• Flash Point: 132℃
• Appearance: /
• Density: 0.965
• Vapor Pressure: 0.00187mmHg at 25°C
• Refractive Index: 1.46
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 5.19±0.31(Predicted)
• CAS DataBase Reference: [1R-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [1R-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexanecarboxylic acid(16052-40-7)
• EPA Substance Registry System: [1R-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexanecarboxylic acid(16052-40-7)

Safety Data

• Hazardous Substances Data: 16052-40-7(Hazardous Substances Data)

Usage

General Description

The chemical "[1R-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexanecarboxylic acid" is a compound with a complex structural formula that contains a cyclohexane ring substituted with an isopropyl and a methyl group. It is classified as a carboxylic acid due to the presence of a carboxyl group, which is a functional group consisting of a carbonyl and a hydroxyl group. [1R-(1alpha,2beta,5alpha)]-2-(isopropyl)-5-methylcyclohexanecarboxylic acid is chiral, with a specific spatial arrangement around the carbon atom, and its optical rotation is designated by the [1R-(1alpha,2beta,5alpha)] notation. It could potentially have applications in organic synthesis, pharmaceuticals, or as a flavoring agent, depending on its properties and reactivity.

InChI:InChI=1/C11H20O2/c1-7(2)9-5-4-8(3)6-10(9)11(12)13/h7-10H,4-6H2,1-3H3,(H,12,13)

Upstream product

• 16052-42-9 (1R,2S,5R)-menthyl chloride 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 124-38-9 carbon dioxide 
• 1217664-77-1 C₁₁H₁₉N 
• 2216-51-5 (-)-menthol 
• 663218-94-8 menthylformic acid 
• 70985-58-9 (1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid 
• 485843-44-5 menthyl 3-carboxaldehyde 
• 63474-24-8 (1R,2S,5R)-(-)menthylmagnesium chloride 
• 80434-59-9 (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxaldehyde 
• 4460-20-2 5-Pentyl-2-((1R)-3c-methyl-6t-isopropyl-cyclohexyl-(1r))-resorcin 
• 67-64-1 acetone 

Downstream Products

• 824947-52-6 (1R)-3c-methyl-6t-isopropyl-cyclohexane-carbanilide-(1r) 
• 68489-09-8 CPS-112 
• 1221279-85-1 menthyl vinyl ketone 
• 70985-58-9 (1S,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carboxylic acid 
• 223750-65-0 C₁₀H₂₁N 

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.

Ester ammonolysis reaction catalyst composition and preparation method of L-menthane carboxamide

The invention discloses an ester ammonolysis reaction catalyst composition and a preparation method of L-menthane carboxamide. The ester ammonolysis reaction catalyst comprises a catalyst and a ligand, wherein the catalyst is cuprous salt CuX, the ligand is a (R)-N, N, N, N-tetraalkyl binaphthylamine compound shown as the specification, wherein R1, R2, R3 and R4 are independently selected from thegroups shown as the specification. Menthyl chloride is used as the starting raw material in the method to react with metal magnesium to prepare menthyl magnesium chloride, then reaction with chloroformate with different substituent groups is carried out to obtain menthyl formate, and then ammonolysis under the catalysis of an ester ammonolysis catalyst composition is conducted to obtain the L-menthane carboxamide. The yield is improved, the production cost is reduced, the optical purity is high, and environmental protection and no wastewater discharge are realized.

Stereochemistry of the Menthyl Grignard Reagent: Generation, Composition, Dynamics, and Reactions with Electrophiles

Menthyl Grignard reagent 1 from either menthyl chloride (2) or neomenthyl chloride (3) consists of menthylmagnesium chloride (1a), neomenthylmagnesium chloride (1b), trans-p-menthane (4), 2-menthene (8), 3-menthene (9), and Wurtz coupling products including symmetrical bimenthyl 13. The diastereomeric ratio 1a/1b was determined in situ by 13C NMR or after D2O quenching by 2H NMR analysis. Hydrolysis of the C-Mg bond proceeds with retention of configuration at C-1. The kinetic ratio 1a/1b from Grignard reagent generation (dr 59:41 at 50 °C in THF) is close to the thermodynamic ratio (56:44 at 50 °C in THF). Carboxylation of 1 at -78 °C separates diastereomers 1a/b to give the anion of menthanecarboxylic acid (19) from 1a, which combines with unreactive 1b to give neomenthylmagnesium menthanecarboxylate (1bI). The kinetics of epimerization for the menthyl/neomenthylmagnesium system was analyzed (ΔH? = 98.5 kJ/mol, ΔS? = -113 J/mol·K for 1bI → 1aI). Reactions of 1 with phosphorus electrophiles proceed stereoconvergently at C-1 of 1a/b to give predominantly menthyl-configured substitution products: PCl3 and 2 equiv of 1 give Men2PCl (6), which hydrolyzes to dimenthylphosphine P-oxide (7), whereas Ph2PCl with 1 equiv of 1 gave P-menthyldiphenylphosphine oxide (27) after workup in air.