40615-17-6

Basic information

• Product Name: 3-AMINO-3,4-DIHYDROQUINOLIN-2(1H)-ONE
• Synonyms: 3-AMINO-3,4-DIHYDROQUINOLIN-2(1H)-ONE;3-amino-3,4-dihydroquinolin-2(1H)-one hydrochloride;2(1H)-Quinolinone, 3-amino-3,4-dihydro-;3-Amino-3,4-dihydro-2(1H)-quinolinone;3-amino-3,4-dihydroquinolin-2(1H)-one hydroiodide;2(1H)-quinolinone, 3-amino-3,4-dihydro-, monohydroiodide;(+/-)-3-Amino-3,4-dihydrocarbostyril;3-Amino-2-oxo-1,2,3,4-tetrahydroquinoline
• CAS NO: 40615-17-6
• Molecular Formula: C9H10N2O
• Molecular Weight: 162.19
• Product Categories: CHIRAL CHEMICALS
• Mol File: 40615-17-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 314-317°(dec)
• Boiling Point: 368.401 °C at 760 mmHg
• Flash Point: 176.603 °C
• Appearance: /
• Density: 1.189
• Vapor Pressure: 1.75E-06mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 14.14±0.40(Predicted)
• CAS DataBase Reference: 3-AMINO-3,4-DIHYDROQUINOLIN-2(1H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-3,4-DIHYDROQUINOLIN-2(1H)-ONE(40615-17-6)
• EPA Substance Registry System: 3-AMINO-3,4-DIHYDROQUINOLIN-2(1H)-ONE(40615-17-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 40615-17-6(Hazardous Substances Data)

Usage

Uses

3-Amino-3,4-dihydroquinolin-2(1H)-one is an intermediate used to prepare thienopyrroles as glycogen phosphorylase inhibitors. It is also an impurity of Melphalan (M216900).

InChI:InChI=1/C9H10N2O.ClH/c10-7-5-6-3-1-2-4-8(6)11-9(7)12;/h1-4,7H,5,10H2,(H,11,12);1H

Upstream product

• 85115-10-2 3-amino-1,2,3,4-tetrahydroquinolin-2-one 
• 1991-82-8 (2S)-2-amino-3-(2-nitrophenyl)propanoic acid 
• 243844-36-2 tert-butyl (2-(chloromethyl)phenyl)-carbamate 
• 88-72-2 1-methyl-2-nitrobenzene 
• 1575604-48-6 methyl 2-amino-3-(2-nitrophenyl)propanoate hydrochloride 
• 164648-12-8 2-amino-3-(2-nitrophenyl)propionic acid hydrochloride 
• 6960-47-0 ethyl 2-(acetylamino)-2-(ethoxycarbonyl)-3-(2-nitrophenyl)propanoate 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 186545-84-6 3-(2-Amino-phenyl)-2-tert-butoxycarbonylamino-propionic acid ethyl ester 
• 552-89-6 2-nitro-benzaldehyde 
• 194611-73-9 tert-butyl 2-oxo-1,2,3,4-tetrahydroquinolin-3-ylcarbamate 
• 135352-46-4 5-(2-nitro-benzylidene)-imidazolidine-2,4-dione 
• 10034-85-2 hydrogen iodide 
• 7670-65-7 3,6-di(2-nitrobenzylidene)piperazine-2,5-dione 

Downstream Products

• 145554-63-8 (3S)-1,2,3,4-tetrahydroquinolin-3-amine 

Relevant articles and documents

(4 + 2) cyclization of aza-o-quinone methides with azlactones: construction of biologically important dihydroquinolinone frameworks

A base-promoted (4 + 2) cyclization of aza-o-quinone methides (aza-o-QMs)in situgenerated fromN-(o-chloromethyl)aryl amides was established. In this approach, azlactones were utilized as competent two-atom reaction partners to undergo (4 + 2) cyclization with aza-o-QMs, which afforded a series of dihydroquinolinone derivatives in overall good yields (up to 98%). This protocol has not only advanced the development of aza-o-QM-involved reactions, but also offered a useful method for constructing biologically important dihydroquinolinone frameworks.

Design, synthesis and biological evaluation of novel 3,4-dihydro-2(1H)-quinolinone derivatives as potential chitin synthase inhibitors and antifungal agents

A series of 3,4-dihydro-2(1H)-quinolinone derivatives contained butenediamide fragment were designed and synthesized. Their inhibition potency against chitin synthase and antimicrobial activities were screened in vitro. The enzymatic assays showed that all the synthesized compounds had inhibition potency against chitin synthase at concentration of 300 μg/mL. Compound 2d displayed excellent potency with inhibition percentage (IP) value of 82.3%, while IP value of the control polyoxin B was 87.5%. Compounds 2b, 2e and 2s whose IP values were above 70% showed good inhibition potency against chitin synthase. Moreover, the IC50 value of 2b was comparable with that of polyoxin B (0.09 mM). The Ki of compound 2b was 0.12 mM and the result from Lineweaver-Burk plot showed that 2b was non-competitive inhibitor to bind chitin synthase. The antifungal experiment showed that these compounds had excellent antifungal activity against fungal strains, especially for candida albicans. The antifungal activities against C .albicans of compounds 2b, 2d, 2e and 2l were comparable with that of fluconazole and were superior to that of polyoxin B. Meanwhile, the other compounds against C. albicans showed better antifungal activity (MIC 2 μg/mL) than polyoxin B except for compound 2n (MIC 4 μg/mL). The trial of drug combination use showed that these synthesized compounds had synergistic effects with fluconazole and polyoxin B. It indicated that these compounds were not competing with polyoxin B to bind with chitin synthase, which was also consistence with the result of enzymatic assays. The antibacterial experiment showed that these compounds had no activity against selected strains including three Gram-positive and three Gram-negative bacteria. These results showed that the designed compounds were chitin synthase inhibitors and had selective antifungal activity.

The enantioselective synthesis of (R)- and (S)-3-amino-3,4-dihydro-1H-[1,8] naphthyridin-2-one

A number of approaches to the enantioselective synthesis of (R)- and (S)-3-amino-3,4-dihydro-1H-[1,8]naphthyridin-2-one were studied. A novel one-pot asymmetric reduction/lactamization provided the desired products in high yield and enantiomeric excess.