15252-45-6

Usage

Uses

Used in Organic Synthesis:
5-Hexyn-1-amine is used as a key intermediate in the synthesis of various organic compounds due to its reactive alkyne and amine functional groups, which allow for a wide range of chemical reactions and the formation of diverse molecular structures.
Used in Pharmaceutical Production:
5-Hexyn-1-amine is used as a building block in the production of pharmaceuticals for its ability to be incorporated into the molecular structures of various drugs, contributing to their therapeutic properties.
Used in Agrochemicals:
5-Hexyn-1-amine is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides, where its reactivity and functional groups can be leveraged to create effective compounds for agricultural applications.
Used in Chemical Research:
5-Hexyn-1-amine is utilized in chemical research as a model compound to study the properties and reactions of alkynes and amines, furthering the understanding of these functional groups and their applications in various chemical processes.
Used in Environmental Safety:
5-Hexyn-1-amine is used in the development of safety protocols and handling procedures to minimize its environmental impact, given its known toxicity to aquatic organisms and its highly flammable nature. This includes the establishment of guidelines for safe storage, transportation, and disposal to prevent harm to ecosystems and human health.

Upstream product

• 2468-56-6 1-iodo-5-hexyne 
• 10297-06-0 1-chloro-5-hexyne 
• 1066-26-8 sodium acetylide 
• 24566-81-2 4-bromo-n-butan-1-amine hydrobromide 
• 74-86-2 acetylene 
• 14918-21-9 5-hexynonitrile 
• 6097-08-1 2-(hex-5-yn-1-yl)isoindole-1,3-dione 
• 5390-04-5 pent-1-yn-5-ol 
• 77758-50-0 4-pentynyl-1-tosylate 
• 210880-57-2 hex-5-yn-1-azide 
• 928-90-5 5-hexyl-1-ol 
• 79496-61-0 hex-5-ynyl methanesulphonate 
• 100-72-1 Tetrahydropyran-2-methanol 
• 18420-41-2 2-(chloromethyl)tetrahydropyran 

Downstream Products

• 145782-21-4 N-(hex-5-yn-1-yl)-4-methylbenzenesulfonamide 
• 102169-54-0 hex-5-yn-1-amine monohydrochloride 
• 873585-83-2 6-(N,N-dibenzylamino)-1-hexyne 
• 870070-94-3 N₁-Boc-Bpa-N₂-hexyneamide 
• 145782-29-2 2-[1-Phenyl-meth-(E)-ylidene]-1-(toluene-4-sulfonyl)-piperidine 
• 1175513-98-0 C₁₅H₁₅NO 
• 1234260-29-7 hex-5-ynyl-(4-nitrophenyl)-amine 
• 151978-58-4 tert-butyl hex-5-yn-1-ylcarbamate 
• 1312656-46-4 C₁₄H₁₈N₂O 
• 912969-02-9 C₃₃H₃₉N₃O₆S₂ 
• 129508-51-6 N-(hex-5-ynyl)benzamide 
• 1402828-98-1 N-(4-ethenylphenyl)-N'-hex-5-yn-1-ylcarbodiimide 
• 1439889-70-9 C₂₀H₂₇Cl₃N₂O₅S 
• 1439890-20-6 C₃₆H₃₉Cl₃N₄O₄S 

Relevant academic research and scientific papers

"Click" chemistry by microcontact printing

(Chemical Equation Presented) Print and click: "Click" chemistry can be efficiently combined with microcontact printing. Synthesis in the nanoscale confinement between an elastomeric stamp and a reactive substrate leads to the desired product within a short time, without a catalyst, and under ambient conditions. As a result, 1-octadecyne could be printed onto an azido-terminated, self-assembled monolayer on a silicon oxide substrate (see scheme).

Substrate mimicry in an activity-based probe that targets the nitrilase family of enzymes

(Chemical Equation Presented) Up and at it: A set of activity-based proteomics probes containing a dipeptide α-chloroacetamide scaffold that targets the nitrilase family of enzymes is described. One member of the nitrilase class, ureidopropionase-β, was found to react selectively with a single probe that mimics the enzyme's endogenous substrate N-carbamoyl β-alanine.

Azerocyclic compounds and their uses

The present invention proposes a nitrogen heterocyclic compound and its use, in particular, the present invention proposes a new compound that effectively inhibits ATX, which is a compound shown in the formula below, or a tautomer of the compound shown be

Design and Synthesis of Oleanolic Acid Trimers to Enhance Inhibition of Influenza Virus Entry

Influenza is a major threat to millions of people worldwide. Entry inhibitors are of particular interest for the development of novel therapeutic strategies for influenza. We have previously discovered oleanolic acid (OA) to be a mild influenza hemagglutinin (HA) inhibitor. In this work, inspired by the 3D structure of HA as a homotrimeric receptor, we designed and synthesized 15 OA trimers with different linkers and central region via the copper-catalyzed azide-alkyne cycloaddition reaction. All of the OA trimers were evaluated for their antiviral activities in vitro, and 12c, 12e, 13c, and 13d were observed to exhibit robust potency (IC50 in the submicromolar range) against influenza A/WSN/33 (H1N1) virus that was stronger than that observed with oseltamivir. In addition, these compounds also displayed strong biological activity against A/Hong Kong/4801/2014 and B/Sichuan/531/2018 (BV). The results of hemagglutination inhibition assays and surface plasmon resonance binding assays suggest that these OA trimers may interrupt the interaction between the HA protein of influenza virus and the host cell sialic acid receptor, thus blocking viral entry. These findings highlight the utility of multivalent OA conjugates to enhance the ligand-target interactions in anti-influenza virus drug design and are also helpful for studying antiviral drugs derived from natural products.

A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions

The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza-Michael reactions.

Self-assembly and solid-state polymerization of butadiyne derivatives with amide and trialkoxyphenyl groups

Three butadiyne derivatives with amide and tri(dodecyloxy)-phenyl (TDP) groups were synthesized, and four solidification methods were applied to obtain their self-assembling states in various conditions. The solids obtained were characterized by the solid-state polymerization behaviors, stretching vibration wavenumbers of N-H bonds of amide groups, powder X-ray diffraction, the thermal behaviors, and scanning electron microscope (SEM) observations. We found that all compounds had at least two polymorphs. Property differences between two polymorphs depended on the compounds. Two compounds showed clear differences in UV-vis spectra of the photo-polymerized solids, i.e., the polydiacetylene (PDA) structure, and irregularly polymerized form, or two PDA structures. The remaining compound showed the same PDA absorption but the monomer melting points were different. All compounds gave the gels in various organic solvents because of the molecular design with amide and TDP groups. SEM observation clarified the relationship between gel appearance and the nanostructures.

Synthesis and solid-state polymerization of a macrocyclic compound with two butadiyne units

A macrocyclic compound 1 with two butadiyne and four dodecyloxy-substituted benzamide moieties was successfully synthesized, and its ring structure was confirmed by the MALDI-TOF mass spectra and the 1HNMR spectra. Compound 1 showed two modifications depending on solvent for the solidification. Characteristic excitonic absorption bands of polydiacetylene were observed at around 500 nm for one of the modifications after UV irradiation. Quantitative conversion of butadiyne moieties to the corresponding polydiacetylene structure was confirmed by the Raman spectra.

Palladium(II)-Catalyzed Regioselective syn-Hydroarylation of Disubstituted Alkynes Using a Removable Directing Group

A palladium(II)-catalyzed regioselective syn-hydroarylation reaction of homopropargyl amines has been developed, wherein selectivity is controlled by a cleavable bidentate directing group. Under the optimized reaction conditions, both dialkyl and alkylaryl alkyne substrates were found to undergo hydroarylation with high selectivity. The products of this reaction contain a 4,4-disubstituted homoallylic amine motif that is commonly seen in drug molecules and other bioactive compounds.

Targeting prostate cancer with compounds possessing dual activity as androgen receptor antagonists and HDAC6 inhibitors

While enzalutamide and abiraterone are approved for treatment of metastatic castration-resistant prostate cancer (mCRPC), approximately 20–40% of patients have no response to these agents. It has been stipulated that the lack of response and the development of secondary resistance to these drugs may be due to the presence of AR splice variants. HDAC6 has a role in regulating the androgen receptor (AR) by modulating heat shock protein 90 (Hsp90) acetylation, which controls the nuclear localization and activation of the AR in androgen-dependent and independent scenarios. With dual-acting AR–HDAC6 inhibitors it should be possible to target patients who don't respond to enzalutamide. Herein, we describe the design, synthesis and biological evaluation of dual-acting compounds which target AR and are also specific towards HDAC6. Our efforts led to compound 10 which was found to have potent dual activity (HDAC6 IC50= 0.0356 μM and AR binding IC50= 0.03 μM). Compound 10 was further evaluated for antagonist and other cell-based activities, in vitro stability and pharmacokinetics.

Synthesis of Strained 1,3-Diene Macrocycles via Copper-Mediated Castro-Stephens Coupling/Alkyne Reduction Tandem Reactions

A copper-mediated macrocyclization involving the reaction of a vinyl iodide and a terminal alkyne followed by an in situ reduction of the enyne intermediate is reported. The reaction generates a conjugated Z-double bond within a strained medium-size lacto