25756-29-0

Usage

Uses

Used in Pharmaceutical Synthesis:
1-cyclohexyl-N-methyl-methanamine is utilized as a precursor in the pharmaceutical industry for the synthesis of various drugs. Its unique chemical structure allows it to be a key component in the development of new medications, contributing to the advancement of healthcare.
Used in Organic Compound Synthesis:
In the field of organic chemistry, 1-cyclohexyl-N-methyl-methanamine serves as a versatile precursor for the synthesis of a range of organic compounds. Its reactivity and solubility properties make it a valuable intermediate in the production of specialty chemicals and materials.
Used in Metal Ion Coordination Chemistry:
1-cyclohexyl-N-methyl-methanamine is employed as a chelating agent in metal ion coordination chemistry. Its ability to form stable complexes with metal ions is crucial for various applications, including the development of catalysts, sensors, and materials with specific properties.
Safety Considerations:
While 1-cyclohexyl-N-methyl-methanamine is considered to have low toxicity, it is important to implement proper safety measures during its handling to minimize the risk of skin, eye, and respiratory tract irritation. This includes the use of appropriate personal protective equipment and adherence to safety guidelines specific to the chemical's properties.

InChI:InChI=1/C8H17N/c1-9-7-8-5-3-2-4-6-8/h8-9H,2-7H2,1H3

Upstream product

• 6830-84-8 N-methylcyclohexanecarboxamide 
• 2550-36-9 Cyclohexylmethyl bromide 
• 74-89-5 methylamine 
• 103-67-3 benzyl-methyl-amine 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 124-38-9 carbon dioxide 
• 3218-02-8 cyclohexylmethylamine 
• 56700-67-5 tert-butyl N-cyclohexylmethylcarbamate 
• 1239325-65-5 tert-butyl N-(cyclohexylmethyl)-N-methylcarbamate 
• 88070-48-8 N-methylbenzamide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 931-51-1 cyclohexylmagnesiumchloride 
• 2719-27-9 cyclohexanylcarbonyl chloride 

Downstream Products

• 735351-38-9 N-cyc!ohexylmethyl-N-methyl-4-nitrobenzamide 
• 911114-89-1 cyclohexylmethyl-methyl-carbamoyl chloride 
• 957113-10-9 C₃₄H₅₀FN₃O₆ 
• 1062653-72-8 C₂₁H₂₇ClN₄O 
• 1250965-30-0 C₁₉H₂₈ClN₃O₃ 
• 1263808-12-3 2-[3-(N-cyclohexylmethyl-N-methylamino)propyl]-10,10a-dihydro-5H-imidazo[1,5-b]isoquinoline-1,3-dione 
• 911114-86-8 (3S,4R)-3-[(cyclohexylmethyl-methyl-carbamoyloxy)-methyl]-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 666861-02-5 3-methyl-1,3-diazaspiro[4.5]decan-2-one 

Relevant academic research and scientific papers

Direct Copper-Catalyzed Three-Component Synthesis of Sulfonamides

First introduced into medicines in the 1930s, the sulfonamide functional group continues to be present in a wide range of contemporary pharmaceuticals and agrochemicals. Despite their popularity in the design of modern bioactive molecules, the underpinning methods for sulfonamide synthesis are essentially unchanged since their introduction, and rely on the use of starting materials with preinstalled sulfur-functionality. Herein we report a direct single-step synthesis of sulfonamides that combines two of the largest monomer sets available in discovery chemistry, (hetero)aryl boronic acids and amines, along with sulfur dioxide, using a Cu(II) catalyst, to deliver a broad range of sulfonamides. Sulfur dioxide is provided by the surrogate reagent DABSO. The reaction tolerates broad variation in both coupling partners, including aryl, heteroaryl and alkenyl boronic acids, as well as cyclic and acyclic alkyl secondary amines, and primary anilines. We validate the method by showing that a variety of drugs, and drug-fragments, can be incorporated into the process.

Titanium(III)-Oxo Clusters in a Metal-Organic Framework Support Single-Site Co(II)-Hydride Catalysts for Arene Hydrogenation

Titania (TiO2) is widely used in the chemical industry as an efficacious catalyst support, benefiting from its unique strong metal-support interaction. Many proposals have been made to rationalize this effect at the macroscopic level, yet the underlying molecular mechanism is not understood due to the presence of multiple catalytic species on the TiO2 surface. This challenge can be addressed with metal-organic frameworks (MOFs) featuring well-defined metal oxo/hydroxo clusters for supporting single-site catalysts. Herein we report that the Ti8(μ2-O)8(μ2-OH)4 node of the Ti-BDC MOF (MIL-125) provides a single-site model of the classical TiO2 support to enable CoII-hydride-catalyzed arene hydrogenation. The catalytic activity of the supported CoII-hydride is strongly dependent on the reduction of the Ti-oxo cluster, definitively proving the pivotal role of TiIII in the performance of the supported catalyst. This work thus provides a molecularly precise model of Ti-oxo clusters for understating the strong metal-support interaction of TiO2-supported heterogeneous catalysts.

Conformational Aspects in the Design of Inhibitors for Serine Hydroxymethyltransferase (SHMT): Biphenyl, Aryl Sulfonamide, and Aryl Sulfone Motifs

Malaria remains a major threat to mankind due to the perpetual emergence of resistance against marketed drugs. Twenty-one pyrazolopyran-based inhibitors bearing terminal biphenyl, aryl sulfonamide, or aryl sulfone motifs were synthesized and tested towards serine hydroxymethyltransferase (SHMT), a key enzyme of the folate cycle. The best ligands inhibited Plasmodium falciparum (Pf) and Arabidopsis thaliana (At) SHMT in target, as well as PfNF54 strains in cell-based assays in the low nanomolar range (18–56 nm). Seven co-crystal structures with P. vivax (Pv) SHMT were solved at 2.2–2.6 ? resolution. We observed an unprecedented influence of the torsion angle of ortho-substituted biphenyl moieties on cell-based efficacy. The peculiar lipophilic character of the sulfonyl moiety was highlighted in the complexes with aryl sulfonamide analogues, which bind in their preferred staggered orientation. The results are discussed within the context of conformational preferences in the ligands.

Amidation of unactivated ester derivatives mediated by trifluoroethanol

A catalytic amidation protocol mediated by 2,2,2-trifluoroethanol has been developed, facilitating the condensation of unactivated esters and amines, furnishing both secondary and tertiary amides. The complete scope and limitations of the method are described, along with modified conditions for challenging substrates such as acyclic secondary amines and chiral esters with retention of chiral integrity.

Heterogeneous CeO2 catalyst for the one-pot synthesis of organic carbamates from amines, CO2 and alcohols

Heterogeneous CeO2 catalyst can catalyze the one-pot synthesis of methyl benzylcarbamate from benzylamine, CO2 and methanol. The yield of methyl benzylcarbamate reached 92% at >99% benzylamine conversion and 92% benzylamine-based selectivity even in the absence of the dehydrating agents. The catalyst is reusable after the calcination at 873 K for 3 h. Various carbamates can be synthesized with good yield and high selectivity by the reaction of amines + CO2 + alcohols over CeO2. The main formation route of methyl benzylcarbamate is suggested to be the reaction of dimethyl carbonate or the precursor of dimethyl carbonate formation with benzylamine.

Selective hydrogenation of amides using ruthenium/ molybdenum catalysts

Recyclable, heterogeneous bimetallic ruthenium/molybdenum catalysts, formed in situ from triruthenium dodecacarbonyl [Ru3(CO)12] and molybdenum hexacarbonyl [Mo(CO)6], are effective for the selective liquid phase hydrogenation of cyclohexylcarboxamide (CyCONH2) to cyclohexanemethylamine (CyCH2NH2), with no secondary or tertiary amine by-product formation. Variation of Mo:Ru composition reveals both synergistic and poisoning effects, with the optimum combination of conversion and selectivity at ca. 0.5, and total inhibition of catalysis evident at ≥1. Good amide conversions are noted within the reaction condition regimes 20100 bar hydrogen and 145-160°C. The order of reactivity of these catalysts towards reduction of different amide functional groups is primary > tertiary ? secondary. In situ HP-FT-IR spectroscopy confirms that catalyst genesis occurs during an induction period associated with decomposition of the organometallic precursors. Ex situ characterisation, using XRD, XPS and EDX-STEM, for active Mo:Ru compositions, has provided evidence for intimately mixed ca. 2.5-4 nm particles that contain metallic ruthenium, and molybdenum (in several oxidation states, including zero).

CALCIUM ION CHANNEL MODULATORS and USES THEREOF

Compounds of formula (I), wherein R1 is hydrogen, hydroxyl or aralkyl; R2 is an optionally substituted alkyl, aryl or heteroaryl (said substituents are selected from hydroxyl, alkoxyl, haloalkoxyl, aryl, heteroaryl, cycloalkyl, amino, monoalkylamino, dialkylamino, alkylsulphonyl, alkylsulphinyl, alkylsulphonylamino, acylamino, saturated or partially unsaturated heterocyclic groups and groups of formula COY); W is selected from oxygen, sulphur, groups of formula NR7, wherein R7 is hydrogen, alkyl, aryl or heteroaryl and groups of formula CR8R9, wherein R8 and R9 are hydrogen, alkyl, aryl or heteroaryl; and X is selected from nitrogen and groups of formula CR10, wherein R10 is hydrogen, alkyl, aryl, heteroaryl, halogen or haloalkyl, inhibit the interaction between Cavx channels and Cavβ proteins and are of use in the treatment and prevention of a number of diseases and conditions including pain and lower urinary tract disorders.

Selective hydrogenation of amides using Rh/Mo catalysts

Rh/Mo catalysts formed in situ from Rh6(CO)16 and Mo(CO)6 are effective for the liquid phase hydrogenation of CyCONH2 to CyCH2NH2 in up to 87% selectivity, without the requirement for ammonia to inhibit secondary amine formation. Use of in situ HP-FTIR spectroscopy has shown that decomposition of metal carbonyl precursors occurs during an extended induction period, with the generation of recyclable, heterogeneous, bimetallic catalysts. Variations in Mo:Rh content have revealed significant synergistic effects on catalysis, with optimum performance at values of ca. 0.6, and substantially reduced selectivities at ≥1. Good amide conversions are noted within the reaction condition regimes 50-100 bar H2 and 130-160 °C. Ex situ characterization of the catalysts, using XRD, XPS and EDX-STEM, has provided evidence for intimately mixed (ca. 2-4 nm) particles that contain metallic Rh and reduced Mo oxides, together with MoO3. Silica-supported Rh/Mo analogues, although active, perform poorly at 150 °C and deactivate during recycle.

New synthesis of tic-hydantoins sigma-1 ligands and pharmacological evaluation on cocaine-induced stimulant effects

Activation of the newly identified σ1 chaperone protein is involved in several aspects of the psychostimulant and addictive effects of cocaine. The development of ligands that selectively target the σ1 protein may lead to putative potent anti-cocaine agen

INDOLE- 3 -GLYOXYLAMIDE DERIVATIVES FOR USE AS CALCIUM ION CHANNEL MODULATORS

Compounds of formula (I) are of use in treating a range of conditions, including pain.