55183-45-4

Usage

Uses

Used in Pharmaceutical Industry:
5-Hexynoyl chloride is used as a reagent in the synthesis of various pharmaceutical compounds for its ability to undergo nucleophilic substitution and addition reactions, contributing to the development of new drugs.
Used in Agrochemical Industry:
5-Hexynoyl chloride is used as a reagent in the production of agrochemicals, enabling the synthesis of compounds that can be used in the development of pesticides and other agricultural products.
Used in Organic Synthesis:
5-Hexynoyl chloride is used as a versatile building block in organic synthesis for its potential to participate in a wide range of chemical reactions, facilitating the creation of diverse organic compounds for various applications.

Upstream product

• 53293-00-8 hex-5-ynoic acid 
• 928-90-5 5-hexyl-1-ol 
• 14918-21-9 5-hexynonitrile 

Downstream Products

• 126140-20-3 1-{3-tert-Butyl-5-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-4-hydroxy-phenyl}-hex-5-yn-1-one 
• 1026274-93-0 1-[4-(tert-Butyl-dimethyl-silanyloxy)-3,5-bis-trifluoromethyl-phenyl]-hex-5-yn-1-one 
• 124837-40-7 1-<3-(1,1-dimethylethyl)-4-hydroxy-5-(2-hydroxy-1,1-dimethylethyl)phenyl>-5-hexyn-1-one 
• 112018-00-5 Tebufelone 
• 1011268-28-2 C₂₂H₃₆N₄O₅S 
• 1067890-59-8 [3R(1'R,4R)]-hex-5-ynoic acid 1'-(2-benzylsulfanyl-4-oxo-azetidin-3-yl)-ethyl ester 
• 864936-07-2 C₁₂H₁₂N₂O₃ 
• 864936-05-0 C₁₂H₁₀Cl₃NO 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 1513888-78-2 (S)-N-(1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl)hex-5-ynamide 
• 1513888-63-5 (S)-4-(1-(adamantan-1-yl)-1H-1,2,3-triazol-4-yl)-N-(1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl)butanamide 

Relevant academic research and scientific papers

Anti-dormant mycobacterial activity and target analysis of nybomycin produced by a marine-derived Streptomyces sp.

Abstract In the course of our search for anti-dormant Mycobacterial substances, nybomycin (1) was re-discovered from the culture broth of a marine-derived Streptomyces sp. on the bioassay-guided separation. Compound 1 showed anti-microbial activity against Mycobacterium smegmatis and Mycobacterium bovis BCG with the MIC of 1.0 μg/mL under both actively growing aerobic conditions and dormancy inducing hypoxic conditions. Compound 1 is also effective to Mycobacterium tuberculosis including the clinically isolated strains. The mechanistic analysis indicated that 1 bound to DNA and induces a unique morphological change to mycobacterial bacilli leading the bacterial cell death.

Supramolecular assembly-induced enhanced emission of electrospun nanofibers

A nucleobase-assembled supramolecular nanofiber is capable of forming network-like polymeric clusters through complementary hydrogen-bonding interactions. It behaves as an effective chromophore that greatly enhances the light emission efficiency of fluorescent fibers, reaching up to three times higher efficiency than the control samples. This journal is

A flexible synthesis of 68Ga-labeled carbonic anhydrase IX (CAIX)-targeted molecules via CBT/1,2-aminothiol click reaction

We herein describe a flexible synthesis of a small library of68Ga-labeled CAIX-targeted molecules via an orthogonal 2-cyanobenzothiazole (CBT)/1,2-aminothiol click reaction. Three novel CBT-functionalized chelators (1-3) were successfully synthesized and labeled with the positron emitter gallium-68. Cross-ligation between the pre-labeled bifunctional chelators (BFCs) and the 1,2-aminothiol-acetazolamide derivatives (8 and 9) yielded six new68Ga-labeled CAIX ligands with high radiochemical yields. The click reaction conditions were optimized to improve the reaction rate for applications with short half-life radionuclides. Overall, our methodology allows for a simple and efficient radiosynthetic route to produce a variety of68Ga-labeled imaging agents for tumor hypoxia.

Synthesis and characterization of monosaccharide lipids as novel hydrogelators

Self-assembly of small molecules is a useful strategy for forming functional supramolecular structures. Three new series of methyl α-d-glucopyranoside derivatives, including esters and carbamates, have been synthesized and characterized. Several of these

Total synthesis of peroxyacarnoates A and D: Metal-mediated couplings as a convergent approach to polyunsaturated peroxides

(Chemical Equation Presented) The first syntheses of peroxyacarnoates A and D, members of a family of enyne-containing alkoxydioxanes, have been achieved on the basis of chemoselective ozonolysis within a polyunsaturated framework and Pd-mediated cross-couplings of a functionalized 1,2-dioxane.

NEW LONG-CHAIN TETRATHIAFULVALENE DERIVATIVES WITH A DIACETYLENE GROUP

The multi-stage synthesis of new long-chain tetrathiafulvalene derivatives containing a diacetylene group at different distances from tetrathiafulvalene moiety - 2-(tetracosa-9,11-diynyl)-, 2-(heptadeca-9,11-diynyl)- and 2-(nonadeca-4,6-diynyl)-6,7-tetrathiafulvalene is described.

Natural Product Micheliolide (MCL) Irreversibly Activates Pyruvate Kinase M2 and Suppresses Leukemia

Metabolic reprogramming of cancer cells is essential for tumorigenesis in which pyruvate kinase M2 (PKM2), the low activity isoform of pyruvate kinase, plays a critical role. Herein, we describe the identification of a nature-product-derived micheliolide (MCL) that selectively activates PKM2 through the covalent binding at residue cysteine424 (C424), which is not contained in PKM1. This interaction promotes more tetramer formation, inhibits the lysine433 (K433) acetylation, and influences the translocation of PKM2 into the nucleus. In addition, the pro-drug dimethylaminomicheliolide (DMAMCL) with similar properties as MCL significantly suppresses the growth of leukemia cells and tumorigenesis in a zebrafish xenograft model. Cell-based assay with knock down PKM2 expression verifies that the effects of MCL are dependent on PKM2 expression. DMAMCL is currently in clinical trials in Australia. Our discovery may provide a valuable pharmacological mechanism for clinical treatment and benefit the development of new anticancer agents.

Small-molecule fluorophores with large stokes shifts: 9-iminopyronin analogues as clickable tags

The design, synthesis, and both experimental and theoretical studies of several novel 9-(acylimino)- and 9-(sulfonylimino)pyronin derivatives containing either an oxygen or a silicon atom at position 10 are reported. These compounds, especially the Si analogues, exhibit remarkably large Stokes shifts (around 200 nm) while still possessing a high fluorophore brightness, absorption bands in the near-UV and visible part of the spectrum, and high thermal and photochemical stabilities in protic solvents. The reason for the observed large Stokes shifts is an intramolecular charge-transfer excitation of an electron from the HOMO to the LUMO of the chromophore, accompanied by elongation of the C9-N bond and considerable solvent reorganization due to hydrogen bonding to the solvent. Due to the photophysical properties of the studied compounds and their facile and high-yielding synthesis, as well as a simple protocol for their bioorthogonal ligation to a model saccharide using a Huisgen alkyne-azide cycloaddition, they represent excellent candidates for biochemical and biological applications as fluorescent tags and indicators for multichannel imaging. 9-(Acylimino)pyronins alter their optical properties upon protonation and may also be used as pH sensors.

Discovery of a Covalent FEM1B Recruiter for Targeted Protein Degradation Applications

Proteolysis-targeting chimeras (PROTACs), heterobifunctional compounds that consist of protein-targeting ligands linked to an E3 ligase recruiter, have arisen as a powerful therapeutic modality for targeted protein degradation (TPD). Despite the popularit

Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes

A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes is reported. The reaction gives the corresponding O-TIPS-protected anti-aldol adducts in high yields and with remarkable stereocontrol and atom economy. Furthermore, the straightforward removal of the achiral scaffold provides enantiomerically pure intermediates of synthetic interest, which involve precursors for anti-α-amino-β-hydroxy and α,β-dihydroxy carboxylic derivatives. Theoretical calculations explain the observed high stereocontrol.