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Usage

Uses

Used in Pharmaceutical Industry:
2-Propen-1-amine, N-(1,1-dimethylethyl)is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its unique structure allows it to be a key component in the synthesis of various drug candidates, contributing to the advancement of novel treatments for various medical conditions.
Used in Chemical Research:
In the field of chemical research, 2-Propen-1-amine, N-(1,1-dimethylethyl)is used as a reagent for the synthesis of new spiro-isoquinolinones and monoazabutadiene compounds. These synthesized compounds have potential applications in various areas, including pharmaceuticals, materials science, and chemical engineering.
Used in Material Science:
The compound's ability to form complex structures makes it a valuable asset in material science. 2-Propen-1-amine, N-(1,1-dimethylethyl)can be used as a building block for the development of new materials with specific properties, such as improved strength, flexibility, or chemical resistance.

Upstream product

• 75-64-9 tert-butylamine 
• 107-05-1 3-chloroprop-1-ene 
• 106-95-6 allyl bromide 
• 845464-89-3 1-(2-allyloxyphenyl)hept-2-yn-1-ol 
• 201230-82-2 carbon monoxide 
• 107-02-8 acrolein 

Downstream Products

• 67616-61-9 N-Allyl-N-tert-butyl-3-chloro-benzamide 
• 71236-84-5 1-tert-butyl-2-phenyl-2,5-dihydro-1H-[1,2]azaphosphole 
• 67651-75-6 N-Allyl-N-tert-butyl-3,4-dichloro-benzamide 
• 84053-73-6 N-Allyl-N-tert.-butyl-β-methyl-zimtsaeureamid 
• 84053-70-3 N-Allyl-N-tert.-butyl-zimtsaeureamid 
• 18366-44-4 3-(tert-butylamino)-1-propanol 
• 59408-55-8 N-Allyl-N-tert-butyl-2-hydroxy-2,2-diphenyl-thioacetamide 

Relevant academic research and scientific papers

Development of a Scalable and Safer Synthesis of Diazeniumdiolates

Although diazeniumdiolates (DAZDs) and the synthetic methods to access DAZDs were discovered over 50 years ago, the current methodology is not safe, has a limited substrate scope, and is not amenable to large-scale production. For example, a recent investigation utilizing the standard methodology to prepare DAZDs resulted in two unexpected explosions, highlighting the need for safer and more practical chemistry. Recently, we have reported a general, scalable, safer, and high-yielding methodology adaptable to large-scale synthesis of diazeniumdiolates in water using a calcium hydroxide base. Herein, we report the full account for the development of the reaction. The merit of this strategy is evidenced by the highly efficient and safer preparation of a key DAZD intermediate, on the kilogram scale, needed for the preparation of MK-8150 (1), a novel O2-alkylated diazeniumdiolate NO donor under investigation as a potent and significant blood-pressure-lowering drug candidate.

An Electron Spin Resonance Study of aminoallyl, Aminopropynyl, and Aminocyanomethyl Radicals

E.s.r. spectra have been obtained for series of N-alkyl-substituted aminoallyl and aminopropynyl radicals and for aminocyanomethyl radicals.The hyperfine splittings indicate that considerable spin density is delocalized on to the NR2 group.The amino group is a more effective acceptor of spin than alkyl-, halogen, hydroxy- or alkyloxy-substituents and only slightly less effective than vinyl substituent.The barrier to rotation about the C-N bond in aminopropynyl radicals was calculated to be 44+/-5 kJ mol-1 from temperature dependence of the e.s.r. line widths, and this leads to a value of 107 kJ mol-1 for the methane-based stabilisation energy of the radical.The geometries, enthalpies of formation, and stabilisation energies of the series of N-alkyl-substituted allyl and propynyl radicals were also investigated by semi-empirical SCF MO methods.

Photoinduced radical-initiated carboxylative cyclization of allyl amines with carbon dioxide

Visible light-promoted CO2 upgrading: a highly efficient and metal-free photochemical method for the carboxylative cyclization of allyl amines with CO2 is reported to prepare perfluoroalkylated oxazolidinones with high efficiency under ambient conditions by using perfluoroalkyl iodides as radical sources.

Phospha derivatives of Tris(2-aminoethyl)amine (tren) and tris(3-aminopropyl)amine (trpn): Synthesis and complexation studies with group 4 metals

The N,N′,N-triphenyl-substituted derivative of tris(2-aminoethyl)phosphine (Ph3-phospha-tren, P(CH2CH2NHR)3, R = Ph) and four derivatives of the related tris(3-aminopropyl)phosphine (phospha-trpn, P(CH2CH2CH2NHR)3, R = iPr, tBu, SitBuMe2, Ph) have been synthesized in addition to the parent phospha-trpn. Out of these ligand systems, only the N,N′,N-triphenyl-substituted phospha-trpn derivative P(CH2CH2CH2NHPh)3 was found to be suitable for coordination to group 4 metals. For titanium, zirconium, and hafnium, the C3-symmetric endo-P-configured dimethylamido complexes Ph[PN3]M(NMe2) of the former ligand have been prepared and converted into the corresponding triflates Ph[PN3]M(OTf). Starting from these triflates, the benzyl complexes Ph[PN3]M(Bn) (M = Ti, Zr, Hf) have been obtained via reaction with Bn2Mg(THF)2. In case of titanium, the benzyl species Ph[PN3]Ti(Bn) is prone to thermal elimination of toluene, which results in the formation of a cyclometalated species. These findings are discussed in context with the very few group 4 trisamidophosphine complexes that have been reported earlier.

PRODUCTION METHOD FOR 2-ALKENYLAMINE COMPOUND

Provided is a method for producing a 2-alkenylamine compound efficiently and at low cost, using a primary or secondary amine compound and a 2-alkenyl compound as the starting materials therefor. The 2-alkenyleamine compound is produced by 2-alkenylating a primary or secondary amine compound, using a specified 2-alkenylating agent and in the presence of a catalyst comprising a complexing agent and a transition metal precursor stabilized by a monovalent anionic five-membered conjugated diene.

Metal-free, mild, nonepimerizing, chemo- and enantio- or diastereoselective N-alkylation of amines by alcohols via oxidation/imine-iminium formation/reductive amination: A pragmatic synthesis of octahydropyrazinopyridoindoles and higher ring analogues

A mild step and atom-economical nonepimerizing chemo- and enantioselective N-alkylating procedure has been developed via oxidation/imine-iminium formation/reduction cascade using TEMPO-BAIB-HEH-Bronsted acid catalysis in DMPU as solvent and a stoichiometric amount of amine. The optimized conditions were further extended for the nonenzymatic kinetic resolution of the chiral amine thus formed under nonenzymatic in situ hydrogen-transfer conditions using VAPOL-derived phosphoric acid (VAPOL-PA) as the Bronsted acid catalyst. The enantioselective cascade of the presented reaction was successfully utilized in the synthesis of octahydropyrazinopyridoindole and its higher ring analogues.

Iron-catalyzed, hydrogen-mediated reductive cyclization of 1,6-enynes and diynes: Evidence for bis(imino)pyridine ligand participation

(Chemical Equation Presented) The bis(imino)pyridine iron dinitrogen complex (iPrPDI)Fe(N2)2 catalyzes the hydrogen-mediated reductive cyclization of enynes and diynes with turnover frequencies comparable to those of established precious metal catalysts. Amino, oxygenated, and carbon-based substrates are readily cyclized to the corresponding hetero- and carbocycles with 5 mol % iron and 4 atm H2 at 23°C. Stoichiometric reactions between selected substrates and the iron compound under a N2 atmosphere established transfer dehydrogenation from an isopropyl aryl substituent to either the enyne or diyne substrate. In situ monitoring of the catalytic reaction by 1H NMR spectroscopy coupled with deuterium labeling experiments established rapid cyclization followed by turnoverlimiting hydrogenation. Copyright

Cascade reactions: A new synthesis of 2-benzofuran-2-ylacetamides by sequential Pd(0)-catalyzed deallylation-Pd(II)-catalyzed aminocarbonylative heterocyclization of 1-(2-allyloxyaryl)-2-yn-1-ols

(Chemical Equation Presented) A general and efficient synthesis of 2-benzofuran-2-ylacetamides 5 starting from 1-(2-allyloxyaryl)-2-yn-l-ols 1, amines 4, and CO, in the presence of catalytic amounts of PdI2 in conjunction with PPh3 and KI, has been developed based on the "sequential homobimetallic catalysis" concept, that is, a process in which two different complexes of the same metal, but in two different oxidation states, promote two catalytic cycles in sequence. The first cycle corresponds to a Pd(0)-catalyzed aminodeallylation of 1 with formation of the free phenol 2, which then undergoes Pd(II)-catalyzed aminocarbonylative heterocyclization to give the final product 5.

Phenyl chloro(thionoformate): A new dealkylating agent of tertiary amines

Phenyl chloro(thionoformate) reacts rapidly with unhindered tertiary aliphatic amines at 20° to give a thiocarbamate and an alkyl chloride. Dialkylcyclohexylamines react surprisingly rapidly to form predominantly cyclohexene. The thiocarbamates are converted into the secondary amine salt by treatment with dimethyl sulfate, followed by hydrolysis with water. Rates of reaction and alkyl group cleavage selectivity in amines were found to be superior or comparable to those previously reported with chloroformates.

Amination of(η3-allyl)dicarbonylnitrosyliron complexes: A route to γ- amino-α,β-unsaturated carboxylic acid derivatives

Amines reacted regioselectively with (ν3-allyl)dicarbonylnitrosyliron complexes having ester group on the allyl ligand to give γ-amino-α,β- unsaturated esters in high yields. A remarkable effect of the substituents attached to the allyl ligand was observed on the reaction rate and regioselectivity of the amination. The methoxycarbonyl group significantly accelerates the reaction rate and enhances the regioselectivity of the reaction. The phenyl group retards the reaction, but enhances the regioselectivity, while alkyl groups retard the reaction and diminish the regioselectivity.