80783-98-8

Usage

Uses

Used in Pharmaceutical Manufacturing:
N-Methoxy-N-Methylcyclohexanecarboxamide is utilized as a protecting group for amines, which is crucial in the synthesis of complex peptide structures. This role is essential for preventing unwanted side reactions during the assembly of peptide chains, thereby ensuring the production of the desired pharmaceutical compounds.
Used in Organic Synthesis:
As a reagent in organic synthesis, N-Methoxy-N-Methylcyclohexanecarboxamide contributes to the formation of various organic compounds. Its properties allow it to participate in a range of chemical reactions, facilitating the synthesis of target molecules.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
N-Methoxy-N-Methylcyclohexanecarboxamide plays a significant role as a chiral auxiliary in asymmetric synthesis. It aids in controlling the stereochemistry of reactions, leading to the selective formation of enantiomers, which is vital for the production of biologically active compounds with specific pharmacological properties.
Used in the Production of Other Organic Compounds:
Beyond its applications in pharmaceuticals and as a chiral auxiliary, N-Methoxy-N-Methylcyclohexanecarboxamide is also employed in the synthesis of a variety of other organic compounds. Its versatility in organic synthesis makes it a valuable tool in the creation of diverse chemical products.

Upstream product

• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 98-89-5 Cyclohexanecarboxylic acid 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 1062512-43-9 C₆H₁₈N₃O₃P 
• 931-51-1 cyclohexylmagnesiumchloride 
• 223570-55-6 N-methoxy-N-methyl-2-pyridyl urethane 
• 1431952-61-2 C₁₂H₂₀O₃ 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 5445-35-2 1-cyclohexyl-1-pentanone 
• 17773-60-3 1-cyclohexyl-2-methylbutan-1-one 
• 2177-34-6 1-cyclohexylprop-2-en-1-one 
• 71338-51-7 α-(phenylseleno)acetylcyclohexane 
• 59304-49-3 1-cyclohexyl-4-penten-1-one 
• 92039-96-8 1-cyclohexyl-2-(pyridin-2-yl)-ethan-1-one 
• 206278-56-0 (Z)-1-Cyclohexyl-2-phenylsulfanyl-hept-2-en-1-one 
• 94719-38-7 1-Cyclohexyl-2-phenylsulfanyl-heptan-1-one 
• 898758-88-8 (cyclohexyl)(oxazol-2-yl)methanone 
• 2789-44-8 cyclohexyl(p-tolyl)methanone 
• 3277-78-9 cyclohexyl (3-tolyl)-methanone 

Relevant academic research and scientific papers

Benzoheterocyclic Oxime Carbamates Active against Mycobacterium tuberculosis: Synthesis, Structure-Activity Relationship, Metabolism, and Biology Triaging

Screening of a library of small polar molecules against Mycobacterium tuberculosis (Mtb) led to the identification of a potent benzoheterocyclic oxime carbamate hit series. This series was subjected to medicinal chemistry progression underpinned by structure-activity relationship studies toward identifying a compound for proof-of-concept studies and defining a lead optimization strategy. Carbamate and free oxime frontrunner compounds with good stability in liver microsomes and no hERG channel inhibition liability were identified and evaluated in vivo for pharmacokinetic properties. Mtb-mediated permeation and metabolism studies revealed that the carbamates were acting as prodrugs. Toward mechanism of action elucidation, selected compounds were tested in biology triage assays to assess their activity against known promiscuous targets. Taken together, these data suggest a novel yet unknown mode of action for these antitubercular hits.

An α-Cyclopropanation of Carbonyl Derivatives by Oxidative Umpolung

The reactivity of iodine(III) reagents towards nucleophiles is often associated with umpolung and cationic mechanisms. Herein, we report a general process converting a range of ketone derivatives into α-cyclopropanated ketones by oxidative umpolung. Mechanistic investigation and careful characterization of side products revealed that the reaction follows an unexpected pathway and suggests the intermediacy of non-classical carbocations.

Magnesium Aldimines Prepared by Addition of Organomagnesium Halides to 2,4,6-Trichlorophenyl Isocyanide: Synthesis of 1,2-Dicarbonyl Derivatives

The selective addition of organomagnesium reagents to 2,4,6-trichlorophenyl isocyanide leading to magnesiated aldimines is reported. These aldimines react with Weinreb amides, ketones, or carbonates to provide the corresponding carbonyl derivatives after acidic cleavage. This allows for an efficient synthesis of 1,2-dicarbonyl compounds and α-hydroxy ketones.

Enolizable β-Fluoroenones: Synthesis and Asymmetric 1,2-Reduction

The hydrofluorination of enolizable ynones with AgF in t-BuOH/DMF is reported. The formation of furans as side products can be suppressed using 2,2′-biphenol. The corresponding β-fluoroenones were obtained with good Z-selectivity. A variety of functional groups are tolerated. β-Fluoroenones are vinylogous acid fluorides whose hydrolysis to vinylogous acids can be avoided under the reported reaction conditions. The asymmetric 1,2-reduction of β-fluoroenones to 3-fluoroallylic alcohols is possible with pinacolborane and a Ni(0) catalyst prepared from a pyrimidyloxazoline ligand.

Synthesis of Difluoromethyl Ketones from Weinreb Amides, and Tandem Addition/Cyclization of o-Alkynylaryl Weinreb Amides

[Difluoro(phenylsulfanyl)methyl]trimethylsilane (PhSCF2SiMe3) underwent a fluoride-induced nucleophilic addition to the carbonyl group of Weinreb amides to provide the corresponding difluoro(phenylsulfanyl)methyl ketones. These were

Copper(I)-Catalyzed Enantioselective Nucleophilic Borylation of Aliphatic Ketones: Synthesis of Enantioenriched Chiral Tertiary α-Hydroxyboronates

A new method was developed for the first catalytic enantioselective borylation of aliphatic ketones. A variety of substrates reacted efficiently with bis(pinacolato)diboron in the presence of a copper(I)/chiral N-heterocyclic carbene complex catalyst to furnish optically active tertiary α-hydroxyboronates with moderate to high enantioselectivities (up to 94 % ee). Notably, the product could be converted into the chiral tertiary alcohol derivative using a stereospecific boron functionalization process. The theoretical study of the mechanism for the enantioselectivity is also described.

A C-H Insertion Approach to Functionalized Cyclopentenones

Cyclopentenones are synthetically versatile structures, and their straightforward construction from alkynone substrates by employing synthetically streamlining C-H insertion is conceptually appealing and of high synthetic potential. But, its implementation is very limited. Herein we report a Au-catalyzed version, which affords 2-bromocyclopent-2-en-1-ones with a broad scope and synthetically desirable diastereoselectivities. The proposed key intermediate capable of the observed insertion into unactivated C-H bonds is a fully functionalized gold vinylidene, which is generated via a novel intermolecular strategy. This flexible access of likely gold vinylidenes opens various opportunities to explore their versatile reactivities.

A deuterated of the IDO inhibitor and its preparation and use (by machine translation)

The invention provides a deuterated of the IDO inhibitor and its preparation and use, as shown in formula I provide compound or its crystalline form, a pharmaceutically acceptable salt, hydrate or solvate. The preparation of the compound or its crystalline form, a pharmaceutically acceptable salt, hydrate or solvate, can be regarded as the IDO inhibitor, can be used for the treatment of IDO related diseases, in particular cancer, viral infection, depression, neurodegenerative disease, trauma, age-related cataract, organ transplant rejection and autoimmune diseases. (by machine translation)

One-pot transition-metal-free synthesis of weinreb amides directly from carboxylic acids

Weinreb amides were prepared directly from carboxylic acids, N,O-dimethylhydroxylamine, and phosphorus trichloride in one pot at 60 °C in toluene in high yields, thus avoiding the separation of the moisture and air sensitive intermediate P[NMe(OMe)]3 in advance. Sterically hindered carboxylic acids also give the corresponding Weinreb amides in excellent yields. Various functional groups are tolerated on the carboxylic acid. The method, which is a simple process and gives high yields, is suitable for large-scale production. Georg Thieme Verlag KG Stuttgart · New York.

Organocatalytic oxidation of aldehydes to mixed anhydrides

TEMPO catalyzes the direct oxidation of aldehydes to mixed anhydrides in the presence of a carboxylic acid. The anhydrides can be converted in situ to esters, secondary, tertiary or Weinreb amides in high yield. Oxidation of the aldehyde directly to 2-propyl esters is also possible using only catalytic amounts of acid. The oxidation reactions are rapid and take place under mild conditions.