58196-33-1

Usage

Uses

Used in Medicinal Chemistry:
7-Hydroxy-1,2,3,4-tetrahydroquinoline is used as a compound with potential biological activity for the development of new pharmaceuticals. Its unique structure and properties make it a candidate for further research and development in the field of medicinal chemistry.
Used in Chemical Research:
7-Hydroxy-1,2,3,4-tetrahydroquinoline is used as a subject of study in chemical research to understand its properties, such as solubility, stability, and reactivity. This knowledge can help in identifying its potential applications and optimizing its synthesis and handling procedures.
Used in Drug Development:
7-Hydroxy-1,2,3,4-tetrahydroquinoline is used as a starting material or intermediate in the synthesis of new drugs. Its structure and potential biological activity make it a valuable component in the development of novel therapeutic agents.
Used in Analytical Chemistry:
7-Hydroxy-1,2,3,4-tetrahydroquinoline is used as a reference compound or standard in analytical chemistry for the calibration of instruments and the development of analytical methods. Its well-defined properties can contribute to the accuracy and reliability of chemical analyses.

InChI:InChI=1/C9H11NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1,3,5,10-11H,2,4,6H2

Upstream product

• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 1023913-73-6 7-methoxy-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester 
• 3334-67-6 3-((3-methoxyphenyl)amino)propanoic acid 
• 536-90-3 m-Anisidine 
• 153856-89-4 7-amino-1,2,3,4-tetrahydroquinoline 
• 22246-18-0 7-hydroxy-3,4-dihydro-2-(1H)-quinolinone 
• 179897-99-5 1-tert-butoxycarbonyl-1,2,3,4-tetrahydro-7-methyloxy-4-quinolinone 
• 879-56-1 7-Methoxy-2,3-dihydro-1H-quinolin-4-one 
• 4964-76-5 7-methoxyquinoline 
• 19500-61-9 7-methoxy-1,2,3,4-tetrahydroquinoline 
• 580-20-1 quinolin-7-ol 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 

Downstream Products

• 62669-73-2 coumarin 339 
• 944413-76-7 C₁₉H₁₅NO₃ 
• 71130-68-2 1-ethyl-7-hydroxy-1,2,3,4-tetrahydroquinoline 
• 53518-16-4 4-trifluoromethyl-6,7,8,9-tetrahydro-pyrano[3,2-g]quinolin-2-one 

Relevant academic research and scientific papers

Development of a C2-Symmetric Chiral aza Spirocyclic Diol

A C2-symmetric chiral spirocyclic diol aza-SPINOL containing a spirooxindole scaffold has been designed, synthesized, and optically resolved. The product could be synthesized on gram scale in an overall yield of 22%. Moreover, elaborations of aza-SPINOL to other chiral ligands as well as the preliminary investigation of the related bisphosphine ligand in the desymmetrization of bisallylic amide were reported.

Cu-Catalyzed Chemoselective Reduction of N-Heteroaromatics with NH3·BH3 in Aqueous Solution

An efficient catalytic system was successfully developed on reduction of N-heteroaromatics with H3N?BH3 as hydrogen source in CuSO4 solution, featuring excellent chemoselectivity as well as very broad functional group tolerance. Various challenging substrates, such as OH-, NH2-, Cl-, Br-, etc., contained quinolines, quinoxalines, 1,5-naphthyridines and quinazolines were all reduced smoothly. Mechanistic studies suggested that [Cu-H] intermediate might be generated from NH3?BH3, which was believed to form with H3N?BH3 in CuSO4 solution.

Small Molecule Control of Morpholino Antisense Oligonucleotide Function through Staudinger Reduction

Conditionally activated, caged morpholino antisense agents (cMOs) are tools that enable the temporal and spatial investigation of gene expression, regulation, and function during embryonic development. Cyclic MOs are conformationally gated oligonucleotide analogs that do not block gene expression until they are linearized through the application of an external trigger, such as light or enzyme activity. Here, we describe the first examples of small molecule-responsive cMOs, which undergo rapid and efficient decaging via a Staudinger reduction. This is enabled by a highly flexible linker design that offers opportunities for the installation of chemically activated, self-immolative motifs. We synthesized cyclic cMOs against two distinct, developmentally relevant genes and demonstrated phosphine-triggered knockdown of gene expression in zebrafish embryos. This represents the first report of a small molecule-triggered antisense agent for gene knockdown, adding another bioorthogonal entry to the growing arsenal of gene knockdown tools.

532nm excited rhodamine fluorescent dye and preparation method thereof

The invention provides 532nm excited rhodamine fluorescent dye and a preparation method thereof. The structure of the 532nm excited rhodamine fluorescent dye is shown as (1), and the fluorescence quantum yield is higher and reaches 0.85 or above in ethanol through modification with different six-membered ring positions at the nitrogen end. Meanwhile, the raw materials used in the invention are cheap and easily available, the synthesis operation is simple, the requirements on experimental conditions are low, and the dye can be widely applied to the field of bioluminescence imaging.

NEAR-INFRARED NERVE-SPARING FLUOROPHORES

Provided are far red to near-infrared nerve-sparing fluorescent compounds, compositions comprising them, and methods of their use in medical procedures.

NERVE-SPECIFIC FLUOROPHORE FORMULATIONS FOR DIRECT AND SYSTEMIC ADMINISTRATION

Nerve-specific fluorophore formulations for direct or systemic administration are described. The formulations can be used in fluorescence-guided surgery (FGS) to aid in nerve preservation during surgical interventions.

Sulfonated 4,7-dichlororhodamine dyes and their application

The invention describes the preparation and use of sulfonated 4,7-dichlororhodamine dyes having the structure: Wherein R1, R4, R5 and R8 are independently hydrogen, —SO3Y where Y is H or a counterion,

Regioselective and Chemoselective Reduction of Naphthols Using Hydrosilane in Methanol: Synthesis of the 5,6,7,8-Tetrahydronaphthol Core

A regioselective and chemoselective method for catalytic synthesis of biologically interesting 5,6,7,8-tetrahydronaphthols by reduction of naphthols was described. The side aromatic hydrocarbons in naphthols were site-selectively reduced, using hydrosilanes in methanol, allowing for retaining functional phenol scaffolds intact. It presents a rare example of using low-cost and air-stable hydrosilane for catalytic reduction of unactivated aromatic hydrocarbons under mild conditions. This reaction is scalable and proceeds in high selectivity without the formation of 1,2,3,4-tetrahydronaphthol byproducts with toleration of sensitive functionalities such as bromide, chloride, fluoride, ketone, ester, and amide.

Selective hydrogenation of quinolines into 1,2,3,4-tetrahydroquinolines over a nitrogen-doped carbon-supported Pd catalyst

In this study, we have developed a sustainable method for the hydrogenation of quinolines to 1,2,3,4-tetrahydroquinolines under mild conditions over a nitrogen-doped carbon-supported Pd catalyst with abundant porous structures (abbreviated as Pd/CN). The mesoporous structure of the nitrogen-doped carbon support was prepared by the pyrolysis of glucose and melamine using eutectic salts of KCl and ZnCl2 as the porogen. Due to the high nitrogen content in the support, Pd nanoparticles were homogeneously dispersed on the surface of nitrogen-doped carbon materials with an ultra-small size of 1.9 nm in a narrow size distribution. The as-prepared Pd/CN catalyst showed high catalytic activity towards the hydrogenation of quinolines at 50 °C and 20 bar H2, affording the corresponding 1,2,3,4-tetrahydroquinolines with yields in the range of 86.6-97.8%. More importantly, the Pd/CN catalyst was highly stable without the loss of its catalytic activity during the recycling experiments. The use of renewable resources to prepare the catalyst makes this method promising for the sustainable 1,2,3,4-tetrahydroquinolines from the hydrogenation of quinolines.

Ring-restricted N-nitrosated rhodamine as a green-light triggered, orange-emission calibrated and fast-releasing nitric oxide donor

Nitric oxide (NO) donors are versatile tools for nitric oxide biology. The biological response of NO is dependent on the transient concentration and the sustained duration. N-Nitrosated rhodamines are photo-triggered and photo-calibrated NO donors. We recently discovered that suppression of the dihedral angle between the N-nitroso fragment with the rhodamine scaffold facilitates NO release. Inspired by this discovery, we developed a fast-releasing NO donor (NOD575) suitable for biological applications, e.g., the pulmonary arterial smooth muscle cells (PASMCs).