58509-59-4

Basic information

• Product Name: 8-(Hydroxyimino)-5,6,7,8-tetrahydroquinoline
• Synonyms: 8-(Hydroxyimino)-5,6,7,8-tetrahydroquinoline;(E)-6,7-dihydroquinolin-8(5H)-one oxiMe;6,7-Dihydro-5H-quinolin-8-one oxiMe
• CAS NO: 58509-59-4
• Molecular Formula: C₉H₁₀N₂O
• Molecular Weight: 162.1885
• Mol File: 58509-59-4.mol

Chemical Properties

• Melting Point: 173-175 °C(Solv: benzene (71-43-2))
• Boiling Point: 353.4±21.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 10.37±0.20(Predicted)
• CAS DataBase Reference: 8-(Hydroxyimino)-5,6,7,8-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-(Hydroxyimino)-5,6,7,8-tetrahydroquinoline(58509-59-4)
• EPA Substance Registry System: 8-(Hydroxyimino)-5,6,7,8-tetrahydroquinoline(58509-59-4)

Safety Data

• Hazardous Substances Data: 58509-59-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-(Hydroxyimino)-5,6,7,8-tetrahydroquinoline is used as an intermediate in the synthesis of 3-heterocyclylacrylamide derivatives. These derivatives act as FaBI protein inhibitors, which are essential for the development of new treatments targeting bacterial infections. By inhibiting the FaBI protein, these derivatives can potentially disrupt the bacterial cell's function and growth, leading to the eradication of the infection.
Used in Antimicrobial Applications:
As a key component in the development of FaBI protein inhibitors, 8-(Hydroxyimino)-5,6,7,8-tetrahydroquinoline plays a significant role in the fight against antibiotic-resistant bacteria. These inhibitors can be incorporated into new antimicrobial drugs, providing a much-needed alternative to traditional antibiotics and helping to combat the growing global threat of antibiotic resistance.

Upstream product

• 28707-60-0 8-benzylidene-5,6,7,8-tetrahydroquinoline 
• 56826-69-8 5,6,7,8-tetrahydro-8-quinolinone 
• 10500-57-9 5,6,7,8-tetrahydroquinoline 

Downstream Products

• 67046-21-3 O-tosyl-6,7-dihydroquinolin-8(5H)-one oxime 
• 67046-22-4 5,6,7,9-tetrahydro-8H-pyrido[2,3-b]azepin-8-one 
• 298181-83-6 5,6,7,8-tetrahydroquinolin-8-yl amine 
• 56826-69-8 5,6,7,8-tetrahydro-8-quinolinone 

Relevant articles and documents

CXCR2 ANTAGONIST

A compound as a CXCR2 antagonist and an application thereof in preparing a drug as a CXCR2 antagonist. In particular, the present invention relates to a compound represented by formula (II) or an isomer or pharmaceutically acceptable salt thereof.

Auxiliary-assisted palladium-catalyzed halogenation of unactivated C(sp3)-H bonds at room temperature

The direct transformation of unactivated C(sp3)-H bonds into C-halogen bonds was achieved by palladium catalysis at room temperature with good functional group tolerance. Some drugs and natural products were readily modified by this method. Merged with substitution reaction, newly formed C-X bonds can be transformed into diverse C-O, C-S, C-C and C-N bonds. A preliminary mechanism study demonstrates that solvent is crucial for C-H activation and the C-H activation step is involved in the rate-limiting step. An isolated Pd(ii) intermediate can be transformed into a halogenated product with the retention of conformation which suggests that concerted reductive elimination from Pd(iv) to form a C-X bond was favored.

Room-temperature copper-catalyzed arylation of dimethylamine and methylamine in neat water

The first room-temperature copper-catalyzed arylations of dimethylamine and methylamine in neat water have been developed. Using a combination of CuI and 6,7-dihydroquinolin-8(5 H)-one oxime as catalyst, dimethylamine is arylated with various aryl halides to give the corresponding products in good to excellent yields. Further, this catalysis enables the selective arylation of methylamine to afford the high yields of monoarylated methylamines as the sole products.

A highly efficient Cu-catalyst system for N-arylation of azoles in water

6,7-Dihydroquinolin-8(5H)-one oxime (L3) was found to serve as a superior ligand for the CuI-catalyzed N-arylation of imidazoles with aryl iodides, bromides, and electron-deficient chlorides in water. Moreover, the CuI/L3 catalyst system enabled the coupling reactions to take place smoothly with high yields under a low catalyst loading (0.1-1 mol% CuI and 0.2-2 mol% L3).

AMD070, a CXCR4 chemokine receptor antagonist: Practical large-scale laboratory synthesis

An efficient and convergent four-step synthetic route to the CXCR4 chemokine receptor antagonist AMD070 (1) has been developed which employs only a single chromatographic step in the entire sequence. Novel reductive amination methods have been developed for the coupling of 2 and 3 in which a dehydrative imine formation is followed by reduction with an attenuated borohydride reagent (zinc chloride and sodium borohydride). Selective extraction methods were employed to purify synthetic intermediates and remove reagents and impurities. A procedure has also been developed to isolate 1 in a pure crystalline form.

CYCLOALKANOPYRIDINE DERIVATIVE

Provided are cycloalkanopyridine derivatives of formula [I]: [wherein the symbols are the same as those stated in the description]. The compounds act as a nociceptin receptor antagonist, and are useful as medicines for diseases associated with a nociceptin receptor, for example, as a reliever against tolerance to a narcotic analgesic; a reliever against dependence on or addiction to a narcotic analgesic; an analgesic enhancer; an antiobesitic or appetite suppressor; a treating or prophylactic agent for cognitive impairment and dementia/amnesia; an agent for treating developmental cognitive abnormality; a remedy for schizophrenia; an agent for treating neurodegenerative diseases; an anti-depressant or treating agent for affective disorder; a treating or prophylactic agent for diabetes insipidus; a treating or prophylactic agent for polyuria; or a remedy for hypotension.

Convenient synthesis of 5,6,7,8-tetrahydroquinolin-8-ylamine and 6,7-dihydro-5H-quinolin-8-one

A novel two-step synthesis of 5,6,7,8-tetrahydroquinolin-8-ylamine, involving regioselective nitrosation of 5,6,7,8-tetrahydroquinoline followed by oxime reduction, is described. Oxime hydrolysis affords 6,7-dihydro-5H-quinolin-8-one.