6837-24-7

Usage

Chemical Properties

clear liquid

Safety Profile

Poison by ingestion. Moderately toxic by inhalation and slun contact. A severe skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C10H17NO/c12-10-7-4-8-11(10)9-5-2-1-3-6-9/h9H,1-8H2

Upstream product

• 96-48-0 4-butanolide 
• 108-91-8 cyclohexylamine 
• 6628-00-8 N-Allylcyclohexylamin 
• 201230-82-2 carbon monoxide 
• 1191-95-3 cyclobutanone 
• 62-53-3 aniline 
• 616-45-5 2-pyrrolidinon 
• 108-85-0 1-bromocyclohexane 
• 98-89-5 Cyclohexanecarboxylic acid 
• 56-12-2 4-amino-n-butyric acid 
• 108-95-2 phenol 
• 108-94-1 cyclohexanone 
• 4641-57-0 1-phenylpyrrolidin-2-one 
• 110-82-7 cyclohexane 

Downstream Products

• 113738-76-4 1-Cyclohexyl-pyrrolidin-2-one; hydrochloride 
• 878679-04-0 1-cyclohexyl-4-dimethylamino-2,3-dihydro-1H-1,4a,5-triaza-s-indacene-8-carboxylic acid methyl ester 
• 1378465-23-6 (E)-3-(benzo[d][1,3]dioxol-5-ylmethylene)-1-cyclohexylpyrrolidin-2-one 
• 1378465-21-4 C₁₇H₂₀BrNO 
• 1378465-25-8 (E)-3-(5-bromo-2-methylbenzylidene)-1-cyclohexylpyrrolidin-2-one 

Relevant academic research and scientific papers

Rh-PVP Catalyzed Reductive Amination of Phenols by Ammonia or Amines to Cyclohexylamines under Solvent-free Conditions

Colloidal metal nanoparticles were examined for reductive amination of phenol by ammonia under mild reaction conditions. The results showed that Rh-PVP was the most active catalyst for reductive amination reaction. Linear, cyclic, and amino alcohols were used as nucleophiles and converted to primary/secondary/tertiary amines. Using this strategy, the synthesis of an industrially important chemical, N-cyclohexyl- 2-pyrrolidone was explored.

Synthesis of Lactams by Reductive Amination of Carbonyl Derivatives with ω-Amino Fatty Acids under Hydrosilylation Conditions

An efficient method for the preparation of lactams from ω-amino fatty acids under hydrosilylation is described. A variety of lactams such as pyrrolidinones, piperidinones and 2-azepanones were selectively synthesised in moderate to excellent yields (29 examples, up to 95 % isolated yields) with a good functional group tolerance. Notably, no metallic based catalyst was required to perform this transformation.

Catalytic Transfer Hydrogenation of Arenes and Heteroarenes

Transfer hydrogenation reactions are of great interest to reduce diverse molecules under mild reaction conditions. To date, this type of reaction has only been successfully applied to alkenes, alkynes and polarized unsaturated compounds such as ketones, imines, pyridines, etc. The reduction of benzene derivatives by transfer hydrogenation has never been described, which is likely due to the high energy barrier required to dearomatize these compounds. In this context, we have developed a catalytic transfer hydrogenation reaction for the reduction of benzene derivatives and heteroarenes to form complex 3-dimensional scaffolds bearing various functional groups at room temperature without needing compressed hydrogen gas.

Decarboxylative sp 3 C-N coupling via dual copper and photoredox catalysis

Over the past three decades, considerable progress has been made in the development of methods to construct sp 2 carbon-nitrogen (C-N) bonds using palladium, copper or nickel catalysis 1,2 . However, the incorporation of alkyl substrates to form sp 3 C-N bonds remains one of the major challenges in the field of cross-coupling chemistry. Here we demonstrate that the synergistic combination of copper catalysis and photoredox catalysis can provide a general platform from which to address this challenge. This cross-coupling system uses naturally abundant alkyl carboxylic acids and commercially available nitrogen nucleophiles as coupling partners. It is applicable to a wide variety of primary, secondary and tertiary alkyl carboxylic acids (through iodonium activation), as well as a vast array of nitrogen nucleophiles: nitrogen heterocycles, amides, sulfonamides and anilines can undergo C-N coupling to provide N-alkyl products in good to excellent efficiency, at room temperature and on short timescales (five minutes to one hour). We demonstrate that this C-N coupling protocol proceeds with high regioselectivity using substrates that contain several amine groups, and can also be applied to complex drug molecules, enabling the rapid construction of molecular complexity and the late-stage functionalization of bioactive pharmaceuticals.

Photoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature

The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for S N2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as well as a lactam and a 2-oxazolidinone) couple with unactivated secondary (and hindered primary) alkyl bromides and iodides using a single set of comparatively simple and mild conditions: inexpensive CuI as the catalyst, no separate added ligand, and C-N bond formation at room temperature. The method is compatible with a variety of functional groups, such as an olefin, a carbamate, a thiophene, and a pyridine, and it has been applied to the synthesis of an opioid receptor antagonist. A range of mechanistic observations, including reactivity and stereochemical studies, are consistent with a coupling pathway that includes photoexcitation of a copper-amidate complex, followed by electron transfer to form an alkyl radical.

Transition Metal-Catalyzed C-H Amination Using Unactivated Amines

One aspect of the invention relates to a method of animation or amidation, comprising the step of combining a substrate, comprising a reactive C—H bond, and an amine or amide, comprising a reactive N—H bond, in the presence of an oxidizing agent and a metal-containing catalyst, thereby forming a product with a covalent bond between the carbon of the reactive C—H bond and the nitrogen of the reactive N—H bond.

Rh-catalyzed intramolecular debenzylative cyclization of amines. Butyrolactams from benzylamines having a chloroacetylene moiety

When benzylamines having a chloroacetylene moiety were heated in wet toluene with a catalytic amount of rhodium trifluoroacetate dimer, intramolecular debenzylative cyclization took place to give butyrolactams. This method is a new entry to selective debenzylation of amines.

Fast, acid-free, and selective lactamization of lactones in ionic liquids

(Chemical Equation Presented) A fast and acid-free one-pot 0.2-30 mmol microwave methodology for direct ionic liquid-mediated preparation of lactams from lactones and primary amines has been developed. The protocol was investigated with a wide range of primary amines and a handful of lactones, including substrates with acid-sensitive substituents. Both γ-lactams and δ-lactams were, despite the complete absence of a Bronsted acid, obtained in useful to excellent yields after only 35 min of microwave processing.

Ring-expanding reaction of cyclopropyl amides with triphenylphosphine and carbon tetrahalide

We succeeded in activating cyclopropyl amides (monoactivated cyclopropane) through the corresponding imidoyl halides prepared in situ in the presence of 2 equiv of PPh3 and 1 equiv of CX4, and the ring-expanding products (N-substituted pyrrolidin-2-ones) were obtained in good yields. The reaction mechanism was investigated on the basis of oxygen-18 tracer experiment.

PRODUCTION OF N-ARYL-2-LACTAM AND N-CYCLOALKYL-2-LACTAM BY REDUCTIVE AMINATION OF LACTONES WITH ARYL AMINES

This invention relates to a process for producing N-aryl-2-lactams and N-cycloalkyl-2-lactams by reductive amination of lactones with aryl amines utilizing a metal catalyst, which is optionally supported.