102169-54-0

Usage

General Description

Hex-5-yn-1-amine hydrochloride is a chemical compound that consists of a hexane backbone with an alkyne group and an amine functional group. It is primarily used as a building block in organic synthesis, especially in the preparation of pharmaceuticals and fine chemicals. The hydrochloride salt form of the compound improves its solubility in water, making it more versatile for certain applications. Hex-5-yn-1-amine hydrochloride may be used in the production of various amino acid derivatives, heterocyclic compounds, and other organic molecules. It is important for researchers and chemists to handle hex-5-yn-1-amine hydrochloride with caution, as it may pose health and safety risks if not properly handled and stored. Overall, hex-5-yn-1-amine hydrochloride is a valuable chemical compound with diverse applications in the field of organic chemistry and drug development.

Upstream product

• 15252-45-6 1-amino-5-hexyne 
• 6097-08-1 2-(hex-5-yn-1-yl)isoindole-1,3-dione 
• 76911-01-8 5-hexynyl p-toluenesulfonate 
• 928-90-5 5-hexyl-1-ol 
• 14918-21-9 5-hexynonitrile 

Downstream Products

• 145782-21-4 N-(hex-5-yn-1-yl)-4-methylbenzenesulfonamide 
• 1227736-77-7 1-tert-butyl-3-(6-(3,5-dimethoxyphenyl)-2-(hex-5-ynylamino)pyrido[2,3-d]pyrimidin-7-yl)urea 
• 930800-38-7 N-(hex-5-yn-1-yl)-2-iodoacetamide 
• 1570114-43-0 C₁₃H₁₃ClN₂O₃ 
• 1570114-41-8 C₁₃H₁₃ClN₂O₃ 
• 1338494-74-8 C₁₉H₂₀FN₃O 

Relevant academic research and scientific papers

A Multidimensional Diversity-Oriented Synthesis Strategy for Structurally Diverse and Complex Macrocycles

Synthetic macrocycles are an attractive area in drug discovery. However, their use has been hindered by a lack of versatile platforms for the generation of structurally (and thus shape) diverse macrocycle libraries. Herein, we describe a new concept in library synthesis, termed multidimensional diversity-oriented synthesis, and its application towards macrocycles. This enabled the step-efficient generation of a library of 45 novel, structurally diverse, and highly-functionalized macrocycles based around a broad range of scaffolds and incorporating a wide variety of biologically relevant structural motifs. The synthesis strategy exploited the diverse reactivity of aza-ylides and imines, and featured eight different macrocyclization methods, two of which were novel. Computational analyses reveal a broad coverage of molecular shape space by the library and provides insight into how the various diversity-generating steps of the synthesis strategy impact on molecular shape.

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

Boron-Catalyzed Silylative Reduction of Nitriles in Accessing Primary Amines and Imines

Silylative reduction of nitriles was studied under transition metal-free conditions by using B(C6F5)3 as a catalyst with hydrosilanes as a reductant. Alkyl and (hetero)aryl nitriles were efficiently converted to primary amines or imines under mild conditions. The choice of silanes was found to determine the selectivity: while a full reduction of nitriles was highly facile, the use of sterically bulky silanes allowed for the partial reduction leading to N-silylimines.

Synthesis and enzymatic incorporation of photolabile dUTP analogues into DNA and their applications for DNA labeling

Two novel photolabile nucleotide triphosphate (NTP) analogues were synthesized through Sonogashira coupling and their enzymatic incorporation into DNA was evaluated with three different DNA polymerases (Taq, Vent exo- and T4) by polymerase chain reaction. Both nucleotide triphosphate analogues were recognized by these DNA polymerases as substrates for primer extension. Light irradiation of PCR products removed the photolabile group and released the amino and carboxyl moieties. Further site-specific dual-labeling for oligodeoxynucleotides (ODNs) and random labeling for a long DNA construct with fluorophores were successfully achieved with incorporation of the photolabile amine modified deoxyuridine triphosphate (dUnTP).

Total synthesis of (+)-nankakurines A and B and (±)-5-epi- nankakurine A

The first total syntheses of the Lycopodium alkaloids (+)-nankakurine A (2), (+)-nankakurine B (3), and the originally purported structure 1 of nankakurine A were accomplished. The syntheses of 2 and 3 feature a demanding intramolecular azomethine imine cycloaddition as the key step for generating the octahydro-3,5-ethanoquinoline moiety and installing the correct relative configuration at the spiropiperidine ring juncture. The cyclization precursor was prepared from octahydronaphthalene ketone 50, which was assembled from enone (+)-9 and diene 48 by a cationic Diels-Alder reaction. The Diels-Alder reactants were synthesized from 5-hexyn-1-ol (16) and (+)-pulegone (49), respectively. The tetracyclic ring system of 1 was generated using an unprecedented nitrogen-terminated aza-Prins cyclization cascade. The enantioselective total syntheses of (+)-nankakurine A (2) and (+)-nankakurine B (3) establish the relative and absolute configuration of these alkaloids and are sufficiently concise that substantial quantities of 2 and 3 were prepared for biological studies. (+)-Nankakurine A and (+)-nankakurine B showed no effect on neurite outgrowth in rat hippocampal H-19 cells over a concentration range of 0.3-10 μM.

Synthesis and biological evaluation of a triazole-based library of pyrido[2,3-d]pyrimidines as FGFR3 tyrosine kinase inhibitors

A library of pyrido[2,3-d]pyrimidines was designed as inhibitors of FGFR3 tyrosine kinase allowing possible interactions with an unexploited region of the ATP binding-site. This library was built-up with an efficient step of click-chemistry giving easy access to triazole-based compounds bearing a large panel of substituents. Among the 27 analogues synthesized, more than half exhibited 55-89% inhibition of in vitro FGFR3 kinase activity at 2 μM and one (19g) was able to inhibit auto-phosphorylation of mutant FGFR3-K650M in transfected HEK cells.

Enantioselective total syntheses of nankakurines A and B: Confirmation of structure and establishment of absolute configuration

Total syntheses of (+)-nankakurine A (2) and (+)-nankakurine B (3) were accomplished by a sequence that employs an intramolecular dipolar cycloaddition of an azomethine imine intermediate to form the azatricyclic moiety and establish the relative configur

Intramolecular hydroamination of alkynes catalysed by late transition metals

The cyclisation of 6-aminohex-1-yne to 2-methyl-1,2-dehydropiperidine in the presence of late transition metal catalysts was examined. The highest catalytic activity was observed for [Cu(CH3CN)4]PF6, as well as with Group 12 metal salts. Slightly lower conversions were obtained with the rhodium(I) and palladium(II) complexes [Rh(COD)(DiPAMP)]BF4 and [Pd(Triphos)][BF4]2. Catalysis was also observed with complexes of all group 9 to 12 metals and [Ru3(CO)12]. All catalytically active complexes contain a metal with a d8 or d10 electronic configuration. This observation allows preliminary conclusions about the mechanism to be made.