32741-89-2

Usage

Uses

Used in Organic Synthesis:
5-(tert-butyl)hexahydro-2H-azepin-2-one is used as a building block in organic synthesis for the creation of various biologically active compounds, leveraging its unique cyclic amine structure and the presence of the tert-butyl group to facilitate the formation of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 5-(tert-butyl)hexahydro-2H-azepin-2-one is used as a key intermediate in the development of new drugs. Its structural properties allow for the exploration of its potential in medicinal chemistry, where it may contribute to the discovery of novel therapeutic agents with improved efficacy and selectivity.
Used in Agrochemical Development:
5-(tert-butyl)hexahydro-2H-azepin-2-one may also find applications in the agrochemical sector, where it could be employed in the synthesis of new pesticides or other agrochemicals. Its potential use in this industry is due to its ability to be modified and functionalized to target specific pests or diseases affecting crops.

InChI:InChI=1/C10H19NO/c1-10(2,3)8-4-5-9(12)11-7-6-8/h8H,4-7H2,1-3H3,(H,11,12)

Upstream product

• 98-53-3 4-tercbutyl-cyclohexanone 
• 4701-98-8 4-tert-butylcyclohexanone oxime 
• 80522-47-0 4-tert-butyl-1-(triisopropylsilyloxy)cyclohexene 

Relevant academic research and scientific papers

Direct synthesis of secondary amides from ketones through Beckmann rearrangement using O-(mesitylsulfonyl)hydroxylamine

The Beckmann rearrangement is a versatile method for the preparation of secondary amides from ketones via oxime intermediates and has been widely used in the synthesis of bioactive natural products and pharmaceuticals. Herein, we have developed a highly efficient direct method for the preparation of secondary amides and lactams from ketones using O-(mesitylsulfonyl)hydroxylamine (MSH). The reactions proceed rapidly at room temperature under mild condition without requiring any additive, and tolerate multiple functional groups. A simple aqueous work-up often furnished the products in excellent yield with high purity.

Synthesis of nitrogen-containing monoterpenoids with antibacterial activity

Incorporation of the Beckmann rearrangement into the presented research resulted in the formation of nitrogen-containing terpenoid derivatives originating from naturally occurring compounds. Both starting monoterpenes and obtained derivatives were subjected to estimation of their antibacterial potential. In the presented study, Staphylococcus aureus was the most sensitive to examined compounds. The Minimal Inhibitory Concentration (MIC) experiments performed on S. aureus demonstrated that the (?)-menthone oxime (?)-8 and (+)-pulegone oxime (+)-13 had the best antibacterial activity among the tested derivatives and starting compounds. Their MIC90 value was 100 μg/mL. The obtained derivatives were also evaluated for their inhibitory activity against bacterial urease. Among the tested compounds, three active inhibitors were found–oxime 14 and lactams (?)-15 and 16 limited the activity of Sporosarcina pasteurii urease with Ki values of 174.3 μM, 43.0 μM and 4.6 μM, respectively. To our knowledge, derivative 16 is the most active antiureolytic lactam described to date.

Cu(OTf) 2 -Catalyzed Beckmann Rearrangement of Ketones Using Hydroxylamine- O -sulfonic Acid (HOSA)

The Beckmann rearrangement (BKR) of ketones to secondary amides often requires harsh reaction conditions that limit its practicality and scope. Herein, the Cu(OTf) 2 -catalyzed BKR of ketones under mild reaction conditions using hydroxylamine- O -sulfonic acid (HOSA), a commercial water soluble aminating agent, is described. This method is compatible with most functional groups and directly provides the desired amides in good to excellent yields.

Directing Group in Decarboxylative Cross-Coupling: Copper-Catalyzed Site-Selective C-N Bond Formation from Nonactivated Aliphatic Carboxylic Acids

Copper-catalyzed directed decarboxylative amination of nonactivated aliphatic carboxylic acids is described. This intramolecular C-N bond formation reaction provides efficient access to the synthesis of pyrrolidine and piperidine derivatives as well as the modification of complex natural products. Moreover, this reaction presents excellent site-selectivity in the C-N bond formation step through the use of directing group. Our work can be considered as a big step toward controllable radical decarboxylative carbon-heteroatom cross-coupling.

One-pot oxidative Mannich-type reaction of lactams with alkyl malonates

One-pot substitution of a C-H bond at the position next to the nitrogen atom of lactams with alkyl malonates proceeded effectively by dehydrogenation of lactams with N-tert-butylbenzenesulfinimidoyl chloride, followed by Mannich-type addition of alkyl malonates.

Beckmann rearrangement of O-4-pentenyl oxime through N- bromosuccinimide-mediated activating process

Beckmann rearrangement of O-4-pentenyl oxime derivatives proceeds in good yield under mild conditions through the formation of a cationic tetrahydrofuranium intermediate in the halocyclization reaction with N- bromosuccinimide.