81467-34-7

Usage

Uses

Used in Pharmaceutical and Agrochemical Development:
3-Oxa-1-azaspiro[4.5]decan-2-one is utilized as a key intermediate in the synthesis of various pharmaceutical and agrochemical compounds. Its unique structure and reactivity make it a promising candidate for the development of new drugs and pesticides.
Used in Antimicrobial and Antifungal Applications:
In the field of microbiology, 3-Oxa-1-azaspiro[4.5]decan-2-one is employed as an antimicrobial and antifungal agent. Its ability to inhibit the growth of certain microorganisms makes it a potential candidate for use in treatments and preventive measures against microbial infections.
Used in Anticancer Research:
3-Oxa-1-azaspiro[4.5]decan-2-one has shown potential as an anticancer agent, warranting further research into its use in oncology. Its potential to target and inhibit the growth of cancer cells positions it as a candidate for future cancer therapies.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the realm of organic chemistry, 3-Oxa-1-azaspiro[4.5]decan-2-one is used as a chiral auxiliary to facilitate asymmetric synthesis. Its unique stereochemistry aids in the production of enantiomerically pure compounds, which is crucial in the development of pharmaceuticals and other chiral molecules.
Used as a Ligand in Transition Metal Ion Complexation:
3-Oxa-1-azaspiro[4.5]decan-2-one also serves as a ligand in the complexation of transition metal ions, which is essential for various catalytic applications. Its ability to form stable complexes with metal ions contributes to the advancement of catalytic processes in organic synthesis and other chemical reactions.

Upstream product

• 4313-56-8 (1-aminocyclohexyl)methanol 
• 57-13-6 urea 
• 105-58-8 Diethyl carbonate 
• 81467-28-9 3-<(1-Hydroxymethyl)cyclohexyl>-1,4,2-dioxazol-5-on 
• 100-49-2 cyclohexylmethyl alcohol 
• 444772-03-6 tetrahydro-2-oxa-3a-aza-cyclopenta[1,3]cyclopropa[1.2]benzen-3-one 
• 1122-60-7 1-nitrocyclohexane 
• 3719-52-6 (1-nitrocyclohexyl)methanol 
• 869111-30-8 cyclohexylmethyl N-hydroxycarbamate 
• 869111-41-1 cyclohexylmethyl N-tosyloxycarbamate 
• 6629-35-2 cyclohexyl methyl carbamate 

Relevant academic research and scientific papers

Titanocene-Catalyzed Radical Opening of N-Acylated Aziridines

Aziridines activated by N-acylation are opened to the higher substituted radical through electron transfer from titanocene(III) complexes in a novel catalytic reaction. This reaction is applicable in conjugate additions, reductions, and cyclizations and suited for the construction of quaternary carbon centers. The concerted mechanism of the ring opening is indicated by DFT calculations.

Copper-catalyzed intramolecular C-H amination

The amino-functionalization of tertiary, secondary and benzylic C-H bonds of tethered carbamates and sulfamates by iodosobenzene is catalyzed by Cu I-diimine complexes in moderate to good yield. Employing homochiral imine-Cucatalysts affords oxazolidinones and oxathiazinanes with modest enantioselectivity.

N-tosyloxycarbamates as reagents in rhodium-catalyzed C-H amination reactions

Metal nitrenes for use in C-H insertion reactions were obtained from N-tosyloxycarbamates in the presence of an inorganic base and a rhodium(II) dimer complex catalyst. The C-H amination reaction proceeds smoothly, and the potassium tosylate that forms as a byproduct is easily removed by filtration or an aqueous workup. This new methodology allows the amination of ethereal, benzylic, tertiary, secondary, and even primary C-H bonds. The intramolecular reaction provides an interesting route to various substituted oxazolidinones, whereas the intermolecular reaction gives trichloroethoxycarbonyl-protected amines that can be isolated with moderate to excellent yields and that cleave easily to produce the corresponding free amine. The development, scope, and limitations of the reactions are discussed herein. Isotopic effects and the electronic nature of the transition state are used to discuss the mechanism of the reaction.

N-tosyloxycarbamates as a source of metal nitrenes: Rhodium-catalyzed C-H insertion and aziridination reactions

The rhodium-catalyzed decomposition of N-tosyloxycarbamates to generate metal nitrenes which undergo intramolecular C-H insertion or aziridination reaction is described. Aliphatic N-tosyloxycarbamates produce oxazolidinones with high yields and stereospecificity through insertion in benzylic, tertiary, and secondary C-H bonds. Intramolecular aziridination occurs with allylic N-tosyloxycarbamates to produce aziridines as single diastereomers. The reaction proceeds at room temperature using a rhodium catalyst and an excess of potassium carbonate and does not require the use of strong oxidant, such as hypervalent iodine reagents. A rhodium nitrene species is presumably involved, as both reactions are stereospecific. Copyright

A silver-catalyzed intramolecular amidation of saturated C-H bonds

Opportunities with silver: A dinuclear silver(I) compound was found to efficiently catalyze the intramolecular amidation of saturated C-H bonds of carbamates and sulfamates (see scheme). This highly regioselective, stereospecific reaction offers a practical method for the construction of cyclic nitrogen-containing organic molecules.

A Rh-catalyzed C-H insertion reaction for the oxidative conversion of carbamates to oxazolidinones

Selective intramolecular alkane oxidations: an RhII carboxylate catalyzed C-H amination reaction facilitates the preparation of 1,2-amino alcohols from primary carbamates. The reaction is stereospecific, providing access to chiral α-branched amines from optically pure starting with no loss in enantiomeric excess (see scheme).

Cyclic Carbonylation of 3-Hydroxycarbohydroxamic Acids with 1,1'-Carbonyldiimidazole

The reaction of 3-hydroxycarbohydroxamic acids 3 with 1,1'-carbonyldiimidazole produces as a function of the substitution of 3 heterocycles of type 1, 4, and 5.In the presence of imidazole the 3-(2-hydroxyalkyl)-1,4,2-dioxazol-5-ones 1 undergo rearrangeme