7150-72-3

Usage

Uses

Used in Pharmaceutical Industry:
Tert-butyl N-ethenylcarbamate is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its protective properties for sensitive functional groups in chemical reactions contribute to the development of new and improved medications.
Used in Agricultural Industry:
Tert-butyl N-ethenylcarbamate is used as a potential antifungal and herbicidal agent. Its application helps in controlling fungal and weed growth, thereby enhancing crop productivity and quality.
Used in Agrochemicals Synthesis:
Tert-butyl N-ethenylcarbamate serves as a chemical intermediate in the synthesis of agrochemicals, contributing to the development of effective pest control solutions for the agricultural sector.
Used in Specialty Chemicals Synthesis:
tert-butyl N-ethenylcarbamate is also utilized as an intermediate in the synthesis of specialty chemicals, broadening its applications across various industries beyond pharmaceuticals and agriculture.

InChI:InChI=1/C7H13NO2/c1-5-8-6(9)10-7(2,3)4/h5H,1H2,2-4H3,(H,8,9)

Upstream product

• 3555-94-0 isocyanatoethene 
• 75-65-0 tert-butyl alcohol 
• 50830-56-3 acryloyl azide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1321892-09-4 N-formyl-N-vinyl-carbamic acid tert-butyl ester 
• 814-68-6 acryloyl chloride 
• 13162-05-5 n-vinylformamide 
• 24608-52-4 tert-butyl chloroformate 

Downstream Products

• 863312-39-4 [6-(2-tert-butoxycarbonylamino-ethyl)-cyclohexa-1,5-dienyl]-(2-triisopropylsilanyloxy-phenyl)-carbamic acid methyl ester 
• 1197815-36-3 C₂₂H₂₉ClN₂O₃ 
• 1030827-13-4 tert-butyl [(3E,4E,6S,7S)-7-ethyl-6-hydroxy-3-{3-[(4-methoxybenzyl)oxy]propylidene}nona-4,8-dien-1-yl]carbamate 
• 1630984-87-0 tert-butyl (5S,7S)-7-((tert-butoxycarbonyl)amino)-3-methyl-5-(4-nitrophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-1-carboxylate 
• 1630984-98-3 tert-butyl (5S,7S)-7-((tert-butoxycarbonyl)amino)-5-(3-chlorophenyl)-3-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-1-carboxylate 
• 1630984-88-1 tert-butyl (5S,7S)-7-((tert-butoxycarbonyl)amino)-5-(3-nitrophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-1-carboxylate 
• 1630985-05-5 tert-butyl (5S,7S)-7-((tert-butoxycarbonyl)amino)-5-(3-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-1-carboxylate 
• 1630985-06-6 tert-butyl (5S,7S)-7-((tert-butoxycarbonyl)amino)-5-(m-tolyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine-1-carboxylate 
• 3555-94-0 isocyanatoethene 

Relevant academic research and scientific papers

Nickel-catalyzed carbodifunctionalization of: N -vinylamides enables access to γ-amino acids

A nickel-catalyzed tandem reaction of N-vinylamides with arylboronic acids and bromodifluoroacetate has been developed. The use of amide carbonyl as a chelating group efficiently furnishes a series of protected α,α-difluoro-γ-amino acid esters. The reaction can also extend to bromoacetate and 2-bromomalonate. The advantages of this protocol are high functional group tolerance and a broad substrate scope, including a variety of N-vinylamides. In particular, the use of removable amide carbonyl groups provides potential opportunities for applications in peptide chemistry and protein engineering.

Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis

A protocol for anti-Markovnikov hydroarylation of alkenes with aryl halides has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light.

Asymmetric Coupling of Carbon-Centered Radicals Adjacent to Nitrogen: Copper-Catalyzed Cyanation and Etherification of Enamides

The first copper-catalyzed asymmetric cyanation and etherification reactions of enamides have been established, where a carbon-centered radical adjacent to a nitrogen atom (CRAN) is enantioselectively trapped by a chiral copper(II) species. Moreover, the asymmetric cyanation of vinyl esters was disclosed as well. These reactions feature very mild reaction conditions and high functional group tolerance, and give a series of chiral α-cyano amides, α-cyano esters and α-hemiaminals in good yields with excellent enantioselectivity. The chiral α-cyano amides can be easily converted into enantioenriched 1,2-diamines and amino acids.

Catalytic Strategy for Regioselective Arylethylamine Synthesis

A mild, modular, and practical catalytic system for the synthesis of the highly privileged phenethylamine pharmacophore is reported. Using a unique combination of organic catalysts to promote the transfer of electrons and hydrogen atoms, this system performs direct hydroarylation of vinyl amine derivatives with a wide range of aryl halides (including aryl chlorides). This general and highly chemoselective protocol delivers a broad range of arylethylamine products with complete regiocontrol. The utility of this process is highlighted by its scalability and the modular synthesis of an array of bioactive small molecules.

Copper-mediated synthesis of N-vinyl ynamides from N-vinyl carbamates

Ynamides are versatile 3-atoms building blocks for organic synthesis as they participate in a variety of ionic, radical and pericyclic processes. Converting ynamides into 5-atom building blocks, such as the yet unreported N-vinyl ynamides, would open new avenues in this fascinating chemistry. We describe herein our efforts towards such goal and demonstrate that the cross-coupling between N-vinyl carbamates and bromo-alkynes using copper(I) thiophene carboxylate, 1,10-phenanthroline and tBuOK in DMSO is a reactive system with an improved profile compared to the classical ynamides syntheses. The advantages and limitations of this copper-mediated reaction are discussed.

Synthetic Access to All Four Stereoisomers of Oxetin

A short synthesis of all four stereoisomers of 3-amino-2-oxetanecarboxylic acid (oxetin) is described. The oxetane core is built using a Paternò-Büchi photochemical [2 + 2] cycloaddition; from the key intermediates, complementary resolution protocols provide access to enantiomerically pure oxetin and epi-oxetin on gram-scale.

Synthesis and antimicrobial evaluation of amixicile-based inhibitors of the pyruvate-ferredoxin oxidoreductases of anaerobic bacteria and Epsilonproteobacte

Amixicile is a promising derivative of nitazoxanide (an antiparasitic therapeutic) developed to treat systemic infections caused by anaerobic bacteria, anaerobic parasites, and members of the Epsilonproteobacteria (Campylobacter and Helicobacter). Amixicile selectively inhibits pyruvate-ferredoxin oxidoreductase (PFOR) and related enzymes by inhibiting the function of the vitamin B1 cofactor (thiamine pyrophosphate) by a novel mechanism. Here, we interrogate the amixicile scaffold, guided by docking simulations, direct PFOR inhibition assays, and MIC tests against Clostridium difficile, Campylobacter jejuni, and Helicobacter pylori. Docking simulations revealed that the nitro group present in nitazoxanide interacts with the protonated N4′-aminopyrimidine of thiamine pyrophosphate (TPP). The ortho-propylamine on the benzene ring formed an electrostatic interaction with an aspartic acid moiety (B456) of PFOR that correlated with improved PFOR-inhibitory activity and potency by MIC tests. Aryl substitution with electron-withdrawing groups and substitutions of the propylamine with other alkyl amines or nitrogen-containing heterocycles both improved PFOR inhibition and, in many cases, biological activity against C. difficile. Docking simulation results correlate well with mechanistic enzymology and nuclear magnetic resonance (NMR) studies that show members of this class of antimicrobials to be specific inhibitors of vitamin B1 function by proton abstraction, which is both novel and likely to limit mutation-based drug resistance.

Lewis Acid Catalyzed [3+2] Coupling of Quinone Monoacetals or Quinone Imine Ketals with Vinylcarbamates

A mild and concise [3+2] coupling of quinone monoacetals or quinone imine ketals with vinylcarbamates promoted by Lewis acid was realized. Various 2-carbamate-2,3-dihydrobenzofurans and 2-carbamate-indolines have been prepared in moderate to good yields.

SYNTHESIS OF MONOCYCLIC N-PYRIDYL-1, 4-AZABORINES AND THEIR PT-COORDINATION COMPLEXES

Monocyclic N-pyridyl-1,4-azaborines and their Pt coordination complexes.

NOVEL COMPOUNDS

Compounds of the formula (I), in which the substituents are as defined in claim 1, are suitable for use as nematicides.