61548-81-0

Basic information

• Product Name: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate
• Synonyms: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate
• CAS NO: 61548-81-0
• Molecular Weight: 234.36
• Mol File: 61548-81-0.mol

Chemical Properties

• CAS DataBase Reference: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate(61548-81-0)
• EPA Substance Registry System: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate(61548-81-0)

Safety Data

• Hazardous Substances Data: 61548-81-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate is utilized as a reagent for the formation of cyclohexylamine derivatives, which are important intermediates in the synthesis of various organic compounds.
Used as a Protecting Group in Organic Chemistry:
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate serves as an effective protecting group for alcohol and phenol functional groups during organic chemistry reactions, preventing unwanted side reactions and facilitating the synthesis of desired products.
Used in Pharmaceutical and Agrochemical Manufacturing:
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl methanesulfonate is also employed in the manufacturing processes of pharmaceuticals and agrochemicals, where its unique structural features contribute to the development of new and effective products.

Upstream product

• 15356-70-4 menthol 
• 124-63-0 methanesulfonyl chloride 
• 2216-51-5 (-)-menthol 

Downstream Products

• 134076-42-9 1-phenylselenenylneomenthane 
• 898543-45-8 2‐azido‐1‐isopropyl‐4‐methylcyclohexane 
• 1678-82-6 trans-1,4-menthane 
• 5113-93-9 (1R)-trans-p-menth-2-ene 
• 2623-23-6 L-menthyl acetate 
• 106137-43-3 (1S,2S,5R)-2-isopropyl-5-methylcyclohexyl formate 
• 107535-12-6 (1S,2S,4R)-2-azido-1-isopropyl-4-methylcyclohexane 
• 2216-52-6 Neomenthol 
• 216019-59-9 neomenthyldiphenylphosphine 
• 180978-26-1 (1S,2S,5R)-1-cyano-2-isopropyl-5-methylcyclohexane 
• 31481-49-9 (1S,2S,5R)-1-benzoyl-2-(1-methylethyl)-5-methylcyclohexan-1-ol 
• 16052-42-9 (1R,2S,5R)-menthyl chloride 
• 87161-58-8 (1S,2S,4R)-2-iodo-1-isopropyl-4-methylcyclohexane 
• 7231-40-5 (+)-(1R,3S,4S)-neomenthylamine 

Relevant articles and documents

Palladium(II)- and rhodium(I)-N-heterocyclic carbene complexes derived from menthol: Synthesis and characterisation

A carbene-Pd(II) complex and a carbene-Rh(I) complex, both derived from commercially available L-(-)-menthol, have been synthesised, characterised and their X-ray single-crystal structures determined.

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.

Enantiopure encaged Verkade's superbases: Synthesis, chiroptical properties, and use as chiral derivatizing agent

Verkade's superbases, entrapped in the cavity of enantiopure hemicryptophane cages, have been synthesized with enantiomeric excess (ee) superior to 98%. Their absolute configuration has been determined by using electronic circular dichroism (ECD) spectros

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 and in vitro antibacterial evaluation of novel 4-substituted 1-menthyl-1,2,3-triazoles

Menthyl 1,4-disubstituted 1,2,3-triazole derivatives of hydroxybenzaldehydes, phenols and bile acids were synthesized via click chemistry. The novel synthesized compounds were evaluated for their in vitro antibacterial activity against Enterococcus faeciu

Enantioselective Rhodium(I)-Catalyzed Additions of Arylboronic Acids to N-1,2,3-Triazole-Isatin Derivatives: Accessing N-(1,2,3-Triazolmethyl)-3-hydroxy-3-aryloxindoles

Oxindoles and triazoles are very privileged frameworks in medicinal chemistry, and thus for the first time we report a catalytic asymmetric route that affords hitherto unknown families of N-(1,2,3-triazolmethyl)-3-hydroxy-3-phenyloxindoles using cheap bio

Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

Treatment of diarylphosphinous acid-borane amides possessing chiral amido functionality with an alkali metal solution in liquid ammonia induced a preferential dearomatization of one aryl substituent at phosphorus leading to the formation of non-equimolar amounts of diastereomers. Diastereoselectivity of dearomatization depends strongly on the structure of a chiral auxiliary.

Synthesis and structures of (-) menthyl and (+) neomenthyl substituted enantio pure bis(1,2,3-triazol-5-ylidene)PdI2 complexes and PEPPSI type (1,2,3-triazol-5-ylidene) (pyridine)PdI2complexes. Comparison of catalytic activities for C-C coupling

(-) Menthol was converted to 1-menthyl-3-methyl-4-phenyltriazolium iodide and 1-neomethyl-3-methyl-4-phenyltriazolium iodide in four steps. These triazolium salts that are enantio pure but diastereo isomers, served as precursors for the synthesis of the corresponding enantio pure bis(1,2,3-triazol-5-ylidene)PdI2 complexes with menthyl and neomenthyl wing tip groups. The palladium complexes were synthesized in high yields using a recently developed mild method under base free and silver free conditions at ambient temperature. These triazolium salts also served as precursors for the synthesis of the corresponding enantio pure PEPPSI type (1,2,3-triazol-5-ylidene) (pyridine)PdI2 complexes. All the complexes were thoroughly characterized by spectroscopic and single crystal XRD data. The relative catalytic activities of these complexes were compared for Suzuki-Miyaura C-C coupling.

Iron(III)-catalyzed halogenations by substitution of sulfonate esters

A novel halogenation reaction from sulfonates catalyzed by iron(III) is described. The reaction can be performed as a stoichiometric or a catalytic version. This reaction provides a convenient strategy for the efficient access to structurally diverse secondary chlorides, bromides and iodides. The stereochemical course of the reaction is governed by the substrate and the experimental conditions. Secondary alcohols modified as quisylates or pysylates are substantially more reactive. Aliphatic quisylates proceed with overall inversion of configuration under catalytic conditions. Chemoselectivity in bismesylates was observed in favour of the secondary mesylate. Additionally, based on the experimental results, a possible catalytic cycle for the halogenation has been proposed.

Inversion of secondary chiral alcohols in toluene with the tunable complex of R3N{single bond}R′COOH

The SN2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R′COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR′COOH is crucial for the SN2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields.