178041-62-8

Basic information

• Product Name: 2(1H)-Quinoxalinone,3,4-dihydro-3-propyl-,(S)-(9CI)
• Synonyms: 2(1H)-Quinoxalinone,3,4-dihydro-3-propyl-,(S)-(9CI);(3S)-3-(1-METHYLETHYL)-3,4-DIHYDROQUINOXALIN-2(1H)-ONE
• CAS NO: 178041-62-8
• Molecular Formula: C11 H14 N2 O
• Molecular Weight: 0
• Product Categories: PIPERIDINE
• Mol File: 178041-62-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(1H)-Quinoxalinone,3,4-dihydro-3-propyl-,(S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Quinoxalinone,3,4-dihydro-3-propyl-,(S)-(9CI)(178041-62-8)
• EPA Substance Registry System: 2(1H)-Quinoxalinone,3,4-dihydro-3-propyl-,(S)-(9CI)(178041-62-8)

Safety Data

• Hazardous Substances Data: 178041-62-8(Hazardous Substances Data)

Usage

Chemical class

Quinoxalinone compounds

Chirality

(S)-(9CI) designation

Substitution

Propyl group attached to the third carbon of the quinoxalinone ring

Hydrogenation state

Dihydro form

Applications

Potential anti-inflammatory, antibacterial, and anticancer agents

Importance of chirality

Affects biological activity and drug development

Upstream product

• 615-83-8 2-bromo-pentanoic acid ethyl ester 
• 95-54-5 1,2-diamino-benzene 
• 13297-36-4 3-propyl-1H-quinoxalin-2-one 
• 50461-74-0 ethyl 2-oxovalerate 

Relevant articles and documents

Metal-free tandem cyclization/hydrosilylation to construct tetrahydroquinoxalines

A one-pot tandem procedure involving cyclization and sequential hydrosilylation of imines and amides under the catalysis of B(C6F5)3 has been developed for the step-economical construction of 1,2,3,4-tetrahydroquinoxalines directly from readily available 1,2-diaminobenzenes, α-ketoesters and low-cost, safe polymethylhydrosiloxane (PMHS). This metal-free approach provides various products in good to excellent yields, and displays a wide range of substrate scope and a high degree of functional group tolerance even to reduction-sensitive moieties. The choice of hydrosilanes is critical to the catalysis, and PMHS has proved to be optimal. Decreasing the amount of PMHS could enable the reaction to stop at the 3,4-dihydroquinoxalin-2(1H)-one stage. The procedure is convenient and scalable, and neither a dried solvent nor an inert atmosphere is required. Moreover, the enantioselective construction of these products was explored, and promising results were achieved.

Versatile (Pentamethylcyclopentadienyl)rhodium-2,2′-Bipyridine (Cp?Rh-bpy) Catalyst for Transfer Hydrogenation of N-Heterocycles in Water

An investigation employing the catalytic system consisting of (pentamethylcyclopentadienyl)rhodium dichloride dimer [Cp?RhCl2]2 and 2,2′-bipyridine (bpy) for transfer hydrogenation of a variety of quinoxalines, quinoxalinones, quinolines and indoles under aqueous conditions with formate as the hydrogen source is reported. This approach provides various tetrahydroquinoxalines, dihydroquinoxalinones, tetrahydroquinolines and indolines in good to excellent yields. The activity of the catalyst towards quinoxalines and quinoxalinones is excellent, with a substrate to catalyst ratio (S/C) of 10000 being feasible. The choice of ligand is critical to the catalysis, and the aqueous phase reduction is shown to be highly pH-dependent, with acidic pH values needed for optimal reduction. The catalyst is easy to access, and the reaction is operationally simple without requiring an inert atmosphere.

Synthetic studies of bioactive quinoxalinones: A facile approach to potent euglycemic and hypolipidemic agents

Substituted quinoxalin-2-ones have been prepared in high yields in a one-pot reaction in which a 1:1 mixture of 1,2-diaminobenzene and appropriate ethyl 2-bromoalkyl/aryl acetate is subjected to microwave irradiation in presence of DBU at 190 °C for 6 min