90086-80-9

Usage

Uses

Used in Organic Synthesis:
Bicyclo[2.2.1]hept-5-ene-2-carbaldehyde oxime is used as a reagent in organic synthesis for the preparation of various organic compounds. Its unique molecular structure allows for the creation of a wide range of chemical products.
Used in Chemical Research:
In the field of chemical research, bicyclo[2.2.1]hept-5-ene-2-carbaldehyde oxime serves as an intermediate, aiding scientists in the development and understanding of new chemical reactions and processes.
Used in Pharmaceutical Research and Manufacturing:
Bicyclo[2.2.1]hept-5-ene-2-carbaldehyde oxime may have potential applications in pharmaceutical research and manufacturing. Its distinctive structure could contribute to the discovery of new drugs or the improvement of existing ones, making it a promising candidate for further exploration in this industry.

InChI:InChI=1/C8H11NO/c10-9-5-8-4-6-1-2-7(8)3-6/h1-2,5-8,10H,3-4H2

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 107-02-8 acrolein 
• 19926-90-0 (+/-)-endo-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde 
• 5453-80-5 5-Norbornene-2-carboxaldehyde 

Downstream Products

• 95-11-4 bicyclo[2.2.1]hept-5-ene-2-carbonitrile 
• 5453-80-5 5-Norbornene-2-carboxaldehyde 

Relevant academic research and scientific papers

The 1-Aza-Cope Rearrangement

The 1-aza-Cope rearrangement of azavinylcyclohexene derivatives were investigated.It was observed that an N-acyl substituent on the 1-aza 1,5-diene provides a sufficient driving force for this normally contrathermodynamic process.Although simple derivatives have high activation energies proceeding in relative low overall yield, a methoxy substituent at C-4 of the aza diene as well as its incorporation into strained bicyclic ring systems facilitates the 1-aza-Cope rearrangement.Because the aza diene precursors are readily available by using the Diels-Alder reaction with acrolein derivatives, this process has synthetic potential for the preparation of nitrogen heterocycles.This scheme is illustrated with the preparation of a hydrolulolidine providing a formal total synthesis of (+/-)-aspidospermine.

THE 1-AZA-COPE REARRANGEMENT

N-Acyl-1-aza-1,5-dienes participate in the Cope rearrangement.

Synthesis of Some Novel Functionalized Monoazatricyclic Ring Systems via Intramolecular Cycloaddition of N-(Bicycloalkenyl)nitrones

The intramolecular cycloaddition of C-phenyl-N-(endo-bicyclooct-6-en-3-ylmethyl)nitrone (3) geneerated in situ from the corresponding hydroxylamine and benzaldehyde gave the adduct 4 in a high yield.Reductive cleavage of 4 afforded 2-endo-hydroxy-4-endo-phenyl-5-azatricyclo3,9>undecane (6).The intramolecular cycloadditions of unsymmetrical N-(endo-bicyclohept-5-en-2-ylmethyl)nitrones (11a,b) and N-(endo-bicyclooct-5-en-2-ylmethyl)nitrones (23a,b) occurred regiospecifically to afford the adducts 12a, b and 24a,b, respectively.Reductive cleavage of these adducts provided a convenient route to functionalized 5-azatricyclo3,8>decanes (15a,b, 16, 17) and 5-azatricyclo3,8>undecanes (27a,b, 28, 29), respectively.The regiochemical and stereochemical assignments of 12a and 24a were proven by X-ray analysis of the methiodides 14a and 26a.