3426-71-9

Usage

Uses

Used in Chemical Synthesis:
BENZYL N-HYDROXYCARBAMATE is used as a reagent in the synthesis of various organic compounds. It is particularly useful in the production of 6-oxa-7-aza-bicyclo[3.2.2]non-8-ene-7-carboxylic acid benzyl ester, which is achieved through its reaction with cyclohepta-1,3-diene. This reaction showcases the versatility of BENZYL N-HYDROXYCARBAMATE in facilitating the formation of complex molecular structures.

InChI:InChI=1/C8H9NO3/c10-8(9-11)12-6-7-4-2-1-3-5-7/h1-5,11H,6H2,(H,9,10)

Upstream product

• 501-53-1 benzyl chloroformate 
• 948586-66-1 N-benzyloxycarbonyl-O-[(3-carboxyphenoxy)carbonyl]hydroxylamine 
• 1257267-02-9 (R)-N-(benzyloxycarbonyl)-O-(2-hydroxy-3-phenylpropanoyl)hydroxylamine 
• 1257267-03-0 (S)-N-(benzyloxycarbonyl)-O-(2-hydroxy-3-phenylpropanoyl)hydroxylamine 
• 1257267-20-1 C₂₃H₃₁NO₅Si 
• 1257267-01-8 C₁₁H₁₃NO₅ 
• 1257267-04-1 benzyl ((3-phenylpropionyl)oxy)carbamate 
• 1257267-05-2 C₁₂H₁₅NO₅ 
• 1257267-06-3 C₁₆H₁₅NO₅ 
• 1138083-43-8 benzyl ((tert-butoxycarbonyl)oxy)carbamate 
• 1257267-09-6 C₂₃H₂₁NO₅ 
• 1257267-07-4 C₁₈H₁₉NO₅ 
• 89854-92-2 (1R,2R)-(2-Amino-cyclohexyl)-methanol 

Downstream Products

• 64596-36-7 benzyl (benzoyloxy)carbamate 
• 63044-78-0 N-benzyloxycarbonyl-9,10-dihydro-9,10-dimethyl-9,10-epoxyiminoanthracene 
• 4950-01-0 N,O-bis-benzyloxycarbonyl-hydroxylamine 
• 4949-97-7 N-Ethoxycarbonyloxy-carbamidsaeure-benzylester 
• 96227-29-1 6-acetyl-3-<(benzyloxy)carbonyl>-5-phenyl-2,3,6-oxadiazabicyclo<2.2.2>oct-7-ene 
• 96212-78-1 5-acetyl-3-<(benzyloxy)carbonyl>-6-phenyl-2,3,5-oxadiazabicyclo<2.2.2>oct-7-ene 
• 105687-17-0 benzyl 2-oxo-2a,6a-dihydrothieto<2,3-e><1,2>oxazine-4-carboxylate 
• 94936-55-7 methyl 3-benzyloxycarbonyl-2-oxa-3,5-diazabicyclo<2.2.2>oct-7-ene-5-carboxylate 
• 94936-26-2 methyl 2-benzyloxycarbonyl-7,8-dihydroxy-3-oxa-2,5-diazabicyclo<2.2.2>octane-5-carboxylate 
• 94936-29-5 methyl 3-benzyloxycarbonyl-7,8-dihydroxy-2-oxa-3,5-diazabicyclo<2.2.2>octane-5-carboxylate 
• 94936-55-7 5-(methoxycarbonyl)-3-<(benzyloxy)carbonyl>-2,3,5-oxadiazabicyclo<2.2.2>oct-7ene 
• 94936-50-2 3-Oxa-2,5-diaza-bicyclo[2.2.2]oct-7-ene-2,5-dicarboxylic acid 2-benzyl ester 5-methyl ester 
• 96212-83-8 6-hydroxy-1-(methoxycarbonyl)-3(R(S))--1,2,3,6-tetrahydropyridine 
• 96212-76-9 5-acetyl-3<(benzyloxy)carbonyl>-6-n-butyl-2,3,5-oxadiazabicyclo<2.2.2>oct-7-ene 

Relevant academic research and scientific papers

Synthesis of N-Oxyureas by Substitution and Cope-Type Hydroamination Reactions Using O-Isocyanate Precursors

Oxy-carbamate O-isocyanate precursors facilitate access to synthetically valuable N-oxyureas via substitution with amines. This work exploits the reactivity of suitable O-isocyanate precursors, identified by a thorough study highlighting the different reactivity of isocyanate masking groups. This led to bench-stable O-isocyanate precursors, offering improved versatility in the synthesis of N-oxyureas, and demonstrates the controlled reactivity of masked O-isocyanates. Suitable precursors also enabled the first example of Cope-type hydroamination of unsaturated hydroxyureas.

An Oxidative Dearomatization Approach to Tetrodotoxin via a Masked ortho-Benzoquinone

Progress toward a stereoselective synthesis of tetrodotoxin (TTX) is presented. Oxidative dearomatization of a tetrasubstituted guaiacol arene yielded a masked ortho-benzoquinone that intercepted an acyl nitroso species generated in situ by the copper-cat

Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions

The acyl nitroso Diels–Alder reaction of 1,3-dienes with electrochemically oxidised hydroxamic acids is described. By using alternating current electrolysis, their typical electro-induced decomposition could be suppressed in favour of the 1,2-oxazine cycloaddition products. The reaction was optimised using Design of Experiments (DoE) and a sensitivity test was conducted. A mixture of triethylamine/hexafluoroisopropanol served as supporting electrolyte in dichloromethane, thus giving products of high purity after evaporation of the volatiles without further purification. The optimised reaction conditions were applied to various 1,3-dienes and hydroxamic acids, giving up to 96 % isolated yield.

Synthesis of Sulfinamidines and Sulfinimidate Esters by Transfer of Nitrogen to Sulfenamides

In this work we report a new synthetic tactic for the straightforward preparation of hardly accessible sulfinamidines and sulfinamide esters, by using a simple metal-free protocol. The process is robust and uses readily available sulfenamides as the S-don

Palladium-Catalyzed Synthesis of Indolines from Aroyloxycarbamates through a Tandem Decarboxylative Amination/Heck/Annulation Reaction

A novel synthesis of functionalized indolines via a Pd-catalyzed tandem decarboxylative amination/Heck/annulation reaction has been developed. This process features operational simplicity, mild conditions, and the use of a readily available and environmentally friendly starting material, namely carboxylic acid. Furthermore, the reaction shows good functional group tolerance and chemical selectivity. (Figure presented.).

An Effective Method for the Synthesis of 1,3-Dihydro-2H-indazoles via N-N Bond Formation

The [4+1] cycloaddition reaction of bifunctional amino reagents has been achieved with in situ formed aza-ortho-quinone methides. Specifically, N-(tosyloxy)carbamates were used as an N1 synthon and bifunctional amino reagents for this transformation, which provides a metal-free, catalyst-free, and oxidant-free strategy to form nitrogen-nitrogen bonds. (Figure presented.).

Synthesis process of Ticagrelor intermediate

The invention discloses a synthesis process of a Ticagrelor intermediate, and belongs to the technical field of medicine synthesis. A compound I is prepared by using hydroxylamine hydrochloride and benzyl chloroformate as raw materials; the compound I and

Synthesis of indoles from aroyloxycarbamates with alkynes: Via decarboxylation/cyclization

An efficient Pd-catalyzed decarboxylation/cyclization of aroyloxycarbamates to realize substituted indoles has been disclosed. Terminal alkynes as the coupling partners lead to site specific 2-substituted indoles through two pathways, while internal alkynes with aroyloxycarbamates can be transformed to 2,3-disubstituted indoles directly. This protocol is further demonstrated by the efficient synthesis of indoles as well as the success of employing inexpensive aryl acids as starting materials to construct C-N bonds by releasing CO2.

Base-Mediated Intramolecular Decarboxylative Synthesis of Alkylamines from Alkanoyloxycarbamates

A general and effective method for the synthesis of alkylamine via intramolecular decarboxylation of alkanoyloxycarbamates is described. The alkanoyloxycarbamates are readily prepared with alkyl carboxylic acids and hydroxylamine. The reaction shows a broad range of substrates (primary and secondary alkyl) with functional tolerance, and the corresponding products were obtained in good yields under mild conditions.

Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction

A new sequential approach for 2-vinylanilines utilizing aryl carboxylic acids as stable, inexpensive and widely available arylating reagents is described. Employing a Pd-POVs catalyst system, this protocol is not only overcoming the restriction barrier of decarboxylative coupling to ortho-substituted substrates, but also provides site-special to create new C(sp2)-N and C(sp2)-C(sp2) bonds. Mechanistic experiments suggest the cleavage of C(sp2)-COOH gives priority to C(sp2)-X bond in this reaction.