99027-88-0

Usage

Uses

Used in Pharmaceutical Industry:
Benzyl 3-oxa-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylate is used as a potential pharmaceutical agent due to its unique molecular structure and the possibility of exhibiting biological activity. Its incorporation into the synthesis of other compounds can lead to the development of new drugs with specific therapeutic effects.
Used in Organic Chemistry Research:
Benzyl 3-oxa-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylate is also used as a subject of study in the field of organic chemistry, where its unique structure and potential reactivity can be further explored. Research into Benzyl 3-oxa-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylate can contribute to the advancement of organic synthesis techniques and the discovery of new chemical reactions and mechanisms.

InChI:InChI=1/C13H13NO3/c15-13(14-11-6-7-12(8-11)17-14)16-9-10-4-2-1-3-5-10/h1-7,11-12H,8-9H2

Upstream product

• 3426-71-9 Benzyl N-hydroxycarbamate 
• 542-92-7 cyclopenta-1,3-diene 
• 501-53-1 benzyl chloroformate 
• 78607-52-0 2-aza-3-oxabicyclo(2.2.1)hept-5-ene hydrochloride 
• 100-64-1 cyclohexanone-oxime 

Downstream Products

• 81357-08-6 benzyl (triphenyl-λ⁵-phosphanilidene)carbamate 
• 99027-97-1 N-benzyloxycarbonylazepine 
• 124555-40-4 2-Oxa-3-aza-bicyclo[2.2.1]heptane-3-carboxylic acid benzyl ester 
• 205675-68-9 cis-4-carbobenzoxyamino-2-cyclopentenol 
• 73903-33-0 (2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid 
• 115890-53-4 1-(benzyloxycarbonyl)kainic acid dimethyl ester 
• 120229-02-9 (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 221910-76-5 (1S,4R)-N-(benzylcarbamoyl)-4-aminocyclopent-2-en-1-ol 
• 205675-73-6 Acetic acid (1S,4R)-4-benzyloxycarbonylamino-cyclopent-2-enyl ester 
• 302906-13-4 [(1R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-cyclopent-2-enyl]-carbamic acid benzyl ester 
• 302906-15-6 ((3aS,4R,6S,6aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-(3-methyl-but-2-enyl)-carbamic acid benzyl ester 
• 302906-17-8 (3aS,3bR,6S,6aS,7aR)-6-Isopropenyl-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester 
• 302906-14-5 [(3aS,4R,6S,6aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-carbamic acid benzyl ester 
• 302906-16-7 Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(3-methyl-but-2-enyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester 

Relevant academic research and scientific papers

Catalytic asymmetric ring opening of 2,3-substituted norbornenes with organometallic reagents: A new formal aza functionalization of cyclopentadiene

(Chemical Equation Presented) An unprecedented regioselective and anti stereoselective asymmetric ring opening of 1,3-cyclopentadiene-heterodienophile cycloadducts, including also 2,3-diazabicyclo[2.2.1]heptenes, with hard alkylmetals and copper-phosphora

Copper-catalyzed aerobic oxidation of N-substituted hydroxylamines: Efficient and practical access to nitroso compounds

A general and efficient aerobic oxidation of N-substituted hydroxylamines is described. The mild reaction conditions employed provide a catalytic and sustainable alternative to stoichiometric oxidation methods to gain access to a range of nitroso compound

A PROCESS FOR THE PREPARATION OF BENZYL [(3AS,4R,6S,6AR)-6-HYDROXY-2,2- DIMETHYLTETRAHYDRO-3AH-CYCLOPENTA[D][1,3]DIOXOL]-4-YL]CARBAMATE AND INTERMEDIATES IN THE PROCESS

The present invention is directed to a process for the preparation of benzyl [(3a S,4R,6S,6a R)-6-hydroxy-2,2-dimethyltetrahydro-3a H-cyclopenta[d][1,3]dioxol-4- yl]carbamate (VI), (VI), to products of said process and the use thereof.

Generation of acyl nitroso compounds by the oxidation of N-acyl hydroxylamines with the Dess-Martin periodinane

The oxidation of hydroxamic acids, N-hydroxyureas and N- hydroxycarbamates with the Dess-Martin periodinane generates the corresponding acyl nitroso compounds that react with conjugated dienes to produce the corresponding cycloadducts.

A concise route to (-)-kainic acid.

A concise route to (-)-kainic acid from enantiopure (+)-cis-4-carbobenzoxyamino-2-cyclopentenol has been devised by employing concurrent Chugaev syn-elimination and intramolecular ene reaction as the key step.

2-Aza-3-Oxabicyclo[2.2.1]heptene hydrochloride: An exceptionally versatile synthon for carbocyclic sugars and nucleosides

The transformation of cyclopentadiene to 5'-desmethylene 1'-aza carbocyclic sugars has been achieved in four steps: 1. Cycloaddition of chloronitrosocyclohexane to 2-aza-3-oxabicyclo[2.2.1]heptene hydrochloride in EtOH-Et2O, 2. Nitrogen functionalization, 3. cis hydroxylation and 4. N-O bond cleavage. The protocols provided enable practical access to a range of 5'-desmethylene carbocyclic sugar analogs whose utility has been illustrated with synthesis of a novel 5'-desmethylene analog of aristeromycin.

Alkoxycarbonylation of alcohols and phenols by nitrosoformates

Unstable neutral radicals [ROCONHO?] 2 and nitrosoformates 3 are formed by oxidation of N-hydroxycarbamates with lead dioxide. In the presence of alcohols or phenols and water they solvolyzed to mixtures of symmetrical 4 and asymmetrical 5 carbonates. The content of asymmetrical carbonates 5 increases with increasing reactivity of the nitrosoformates 3 formed, temperature, the content of water in the reaction mixture, and with decreasing reactivity of alcohol. The reactivities of individual alcohols have been evaluated with the help of competitive alcoholysis. The new method of alcohol or phenol alkoxylation has been verified experimentally by preparing six asymmetrical carbonates which were obtained in 34 to 47% yields.

EXCITATORY AMINO ACID RECEPTOR ANTAGONISTS

The present invention provides novel compounds that affect excitatory amino acid receptors and are useful in the treatment of neurological disorders. This invention also provides synthetic methods for the preparation of the novel compounds.

Formation and Reactions of C-Nitrosoformate Esters, A New Class of Transient Dienophiles

Oxidation of N-hydroxycarbamic esters, ROCONHOH, with tetraethylammonium or sodium periodate in the presence of conjugated dienes gave N-alkoxycarbonyl-3,6-dihydro-2H-1,2-oxazines, formed apparently by cycloaddition of transient C-nitrosoformate esters, ROCONO, with the dienes.Cleavage of various N-alkoxycarbonyl derivatives under mild conditions is exemplified.The cycloadduct (10a) of benzyl nitrosoformate and 9,10-dimethylanthracene decomposed in benzene at 80 deg C in the presence of thebaine (3) to give the corresponding adduct (4a) of thebaine, together with 9,10-dimethylanthracene.Similarly, the adduct (6b) of 2,2,2-trichloroethyl nitrosoformate and cyclopentadiene, when heated with ergosteryl acetate, gave the corrresponding adduct (8b) of the steroid.Benzyl and t-butyl azidoformates decomposed in dimethyl sulphoxide at 115-130 deg C in the presence of thebaine to give the adducts (4a) and (4c) of benzyl and t-butyl nitrosoformate and the alkaloid.The other, major products were the sulphoximides (20a) and (20c).Alkoxycarbonylnitrenes, therefore, attack dimethyl sulphoxide either on sulphur, to give sulphoximides, or on oxygen, to give nitrosoformates.Benzyl nitrosoformate, generated thermally from either the adduct (10a) or (6a), reacted with triphenylphosphine to give, apparently, benzyloxycarbonylnitrene which attacked the solvent, benzene, to form N-benzyloxycarbonylazepine (24a).The adduct (6c) of t-butyl nitrosoformate and cyclopentadiene behaved likewise to give the azepine (24c).The reaction of (6c) with triphenylphosphine in benzene or dichloromethane gave a small quantity of 5,5-dimethyloxazolidin-2-one (26), a known cyclisation product of t-butyloxy-carbonylnitrene.