415936
3,4-Dihydro-2(1H)-quinolinone
98%
Synonym(s):
Hydrocarbostyril
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About This Item
Empirical Formula (Hill Notation):
C9H9NO
CAS Number:
Molecular Weight:
147.17
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Assay
98%
mp
165-167 °C (lit.)
SMILES string
O=C1CCc2ccccc2N1
InChI
1S/C9H9NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-4H,5-6H2,(H,10,11)
InChI key
TZOYXRMEFDYWDQ-UHFFFAOYSA-N
General description
Series of 3,4-dihydro-2(1H)-quinolinone derivatives having sigma-1 receptor (σ1R) antagonist activity have been synthesized. 3,4-dihydro-2((1)H)-quinolinones have been synthesized using N-(1′-alkoxy)cyclopropyl-2-haloanilines as starting reagent. Cyclopropane ring expansion in the presence of palladium catalyst is the major step involved in the synthesis. Library of 3,4-dihydro-2(1H)-quinolinones have been synthesized through the rearrangement of β-lactam intermediates on the solid-phase
Application
3,4-Dihydro-2(1H)-quinolinone may be employed as medium supplement in the culture medium of Pseudomonas ayucida during enrichment culture experiments.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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So Youn Park et al.
Behavioural brain research, 365, 133-140 (2019-03-10)
Cerebrovascular dysfunction is associated with cognitive impairment in vascular dementia patients. This study aimed to explore augmented improvement of cognition and memory by aripiprazole add-on for cilostazol treatment in vascular dementia model. Male C57BL/6 mice were subjected to BCAS, and
Synthesis of 4-amino-3, 4-dihydro-2 (1H)-quinolinones via β-lactam intermediates on the solid-phase.
Pei Y, et al.
Tetrahedron Letters, 38(19), 3349-3352 (1997)
Selective removal of nitrogen from quinoline and petroleum by Pseudomonas ayucida IGTN9m.
Kilbane JJ, et al.
Applied and Environmental Microbiology, 66(2), 688-693 (2000)
Fabio Del Bello et al.
Journal of medicinal chemistry, 63(11), 5763-5782 (2020-05-07)
A series of novel 1,4-dioxane analogues of the muscarinic acetylcholine receptor (mAChR) antagonist 2 was synthesized and studied for their affinity at M1-M5 mAChRs. The 6-cyclohexyl-6-phenyl derivative 3b, with a cis configuration between the CH2N+(CH3)3 chain in the 2-position and
Takayuki Tsuritani et al.
Organic letters, 11(5), 1043-1045 (2009-02-06)
N-(1'-Alkoxy)cyclopropyl-2-haloanilines are transformed to 3,4-dihydro-2((1)H)-quinolinones via palladium-catalyzed cyclopropane ring expansion. The reaction tolerates a variety of functional groups such as ester, nitrile, ether, and ketone groups.
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