44768-33-4

Usage

InChI:InChI=1/C7H13N/c1-3-5-7-8-6-4-2/h2,8H,3,5-7H2,1H3/p+1

Upstream product

• 109-73-9 N-butylamine 
• 106-96-7 propargyl bromide 
• 89796-20-3 N-(2-bromoprop-2-enyl)-N-butylamine 
• 75858-58-1 C₁₁H₂₄N₃OP 
• 624-65-7 2-propynyl chloride 

Downstream Products

• 624-67-9 Propargylic aldehyde 
• 554-68-7 triethylamine hydrochloride 
• 39536-61-3 N-butylpentylamine 
• 1332362-36-3 N-(((2S,3S)-3-phenyloxiran-2-yl)methyl)-N-(prop-2-yn-1-yl)butan-1-amine 
• 1332362-40-9 (7S,8R)-5-butyl-8-phenyl-5,6,7,8-tetrahydro-4H-[1,2,3]triazolo[1,5-a][1,4]diazepin-7-ol 
• 439571-70-7 1-butyl-4-methyl-2-phenyl-1H-imidazole 
• 445255-32-3 N-(3-phenylprop-2-yn-1-yl)butan-1-amine 
• 861956-74-3 Se-phenyl N-butyl-N-(prop-2-ynyl)carbamoselenoate 

Relevant academic research and scientific papers

Controllable encapsulation of silver nanoparticles by porous pyridine-based covalent organic frameworks for efficient CO2conversion using propargylic amines

The conversion of CO2 into value-added chemicals is an attractive alternative to produce valuable fuels and chemicals. In this work, we demonstrate two pyridine-based covalent organic frameworks (COFs) with rich porosity for the size-controlled synthesis

Non-Noble-Metal Metal-Organic-Framework-Catalyzed Carboxylative Cyclization of Propargylic Amines with Atmospheric Carbon Dioxide under Ambient Conditions

The coupling reaction of propargylic amines and carbon dioxide (CO2) to synthesize 2-oxazolidinones is an important reaction in industrial production, and yet harsh reaction conditions and noble-metal catalysts are often required to achieve high product yields. Herein, one novel noble-metal-free three-dimensional framework, [Mg3Cu2I2(IN)4(HCOO)2(DEF)4]n (1), assembled by magnesium and copper clusters was synthesized and applied to this reaction. Compound 1 displays excellent solvent stability. Importantly, 1, acting as heterogeneous catalyst, can highly catalyze the cyclization of propargylic amines with CO2 under atmospheric pressure at room temperature, which can be recycled at least five times without an obvious decrease of the catalytic activity. NMR spectroscopy, coupled with 13C-isotope- and deuterium-labeling experiments, clearly clarifies the mechanism of this catalytic system: CO2 was successfully captured and converted to the product of 2-oxazolidinones, the CC bond of propargylic amines can be effectively activated by 1, and proton transfer was involved in the reaction process. Density functional theory calculations are further conducted to uncover the reaction path and the crucial role of compound 1 during the reaction.

Highly Efficient Conversion of Propargylic Amines and CO2 Catalyzed by Noble-Metal-Free [Zn116] Nanocages

The reaction of propargylic amines and CO2 can provide high-value-added chemical products. However, most of catalysts in such reactions employ noble metals to obtain high yield, and it is important to seek eco-friendly noble-metal-free MOFs catalysts. Here, a giant and lantern-like [Zn116] nanocage in zinc-tetrazole 3D framework [Zn22(Trz)8(OH)12(H2O)9?8 H2O]n Trz=(C4N12O)4? (1) was obtained and structurally characterized. It consists of six [Zn14O21] clusters and eight [Zn4O4] clusters. To our knowledge, this is the highest-nuclearity nanocages constructed by Zn-clusters as building blocks to date. Importantly, catalytic investigations reveal that 1 can efficiently catalyze the cycloaddition of propargylic amines with CO2, exclusively affording various 2-oxazolidinones under mild conditions. It is the first eco-friendly noble-metal-free MOFs catalyst for the cyclization of propargylic amines with CO2. DFT calculations uncover that ZnII ions can efficiently activate both C≡C bonds of propargylic amines and CO2 by coordination interaction. NMR and FTIR spectroscopy further prove that Zn-clusters play an important role in activating C≡C bonds of propargylic amines. Furthermore, the electronic properties of related reactants, intermediates and products can help to understand the basic reaction mechanism and crucial role of catalyst 1.

Efficient Conversion of Tertiary Propargylamides into Imidazoles via Hydroamination-Cyclization

A method to convert tertiary N -propargylamides into 1,2,4-trisubstituted imidazoles using ammonium chloride and zinc triflate as the catalyst is reported. The method is convenient, practical and employs conventional heating. It is also applicable to N -propargyl lactams and tends to populate the so-called 'lead-like' chemistry space.

Ln[N(SiMe3)2]3-Catalyzed Cross-Diinsertion of C≡N/C≡C into an N-H Bond: Facile Synthesis of 1,2,4-Trisubstituted Imidazoles from Propargylamines and Nitriles

A lanthanide-catalyzed sequential insertion of C≡N and C≡C into an N-H bond is presented. The convenient reaction, which proceeds under mild conditions, is an efficient method for preparing 1,2,4-trisubstituted imidazoles directly from readily available propargylamines and nitriles.

An expeditious and atom-economic synthesis of lead-like, medicinally important 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones

We have developed an expeditious and atom-economic synthesis of lead-like, privileged 4,5-dihydropyrazolo[1,5-a]pyrazin-6-ones, which is based on Sonogashira coupling and a two-step condensation with hydrazine hydrate leading to two ring-forming events, with full control over the two elements of diversity present.

Palladium-catalyzed intramolecular selenocarbamoylation of alkynes with carbamoselenoates: Formation of α-alkylidene-β-lactam framework

Pd-catalyzed intramolecular selenocarbamoylation of alkynes leading to α-alkylidene-β-lactams was developed. This reaction can be applied to thiocarbamoylation and to the synthesis of δ- and ε-lactams and a cyclobutanone. Copyright

Aliphatic propargylamines as cellular rescue agents

The present invention relates to the use of a group of propargylamines of the general formula (I) STR1 wherein R1 is hydrogen or CH3 and R2 is (CH2)n CH3 and n is an integer from 0 to 16, and salts thereof, as cellular rescue agents in the treatment and prevention of diseases in which cell death occurs by apoptosis. Some of the compounds of formula I are novel. The invention is also directed to the use of these compounds in the treatment of these diseases, as well as to processes for the preparation of the compounds.

Novel cleavage of propargylamines by reaction with organolithium compounds

Treatment of secondary aliphatic 2-bromoallylamines with an excess of an organolithium compound led to saturated amines in which the organic group of the organolithium compound is incorporated at the α carbon. On the other hand, the successive reaction of the former amines with BuLi and t-BuLi between -80°C and rt gave 1,3-diamines or hexahydropyrimidines depending on the reaction time. The formation of these unexpected products involves initial generation of lithium propargylamides, which subsequently undergo cleavage of the C propargylic-C acetylenic bond induced by the organolithium present in each case in the reaction medium. A mechanism which takes into account all the different reaction products has been proposed and additionally supported by successful trapping of dilithium acetylide.