5021-47-6

Basic information

• Product Name: 2-PHENYL-1,2,3,4-TETRAHYDRO-QUINOXALINE
• Synonyms: 2-PHENYL-1,2,3,4-TETRAHYDRO-QUINOXALINE
• CAS NO: 5021-47-6
• Molecular Formula: C₁₄H₁₄N₂
• Molecular Weight: 210.27436
• Mol File: 5021-47-6.mol

Chemical Properties

• Melting Point: 94-99°C
• Boiling Point: 395.5°Cat760mmHg
• Flash Point: 258.2°C
• Appearance: /
• Density: 1.092g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.59
• PKA: 3.84±0.70(Predicted)
• CAS DataBase Reference: 2-PHENYL-1,2,3,4-TETRAHYDRO-QUINOXALINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-1,2,3,4-TETRAHYDRO-QUINOXALINE(5021-47-6)
• EPA Substance Registry System: 2-PHENYL-1,2,3,4-TETRAHYDRO-QUINOXALINE(5021-47-6)

Safety Data

• Hazard Codes: T,N
• Statements: 25-51/53
• Safety Statements: 45-61
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 5021-47-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H14N2/c1-2-6-11(7-3-1)14-10-15-12-8-4-5-9-13(12)16-14/h1-9,14-16H,10H2

Upstream product

• 1074-12-0 phenylglyoxal hydrate 
• 95-54-5 1,2-diamino-benzene 
• 96-09-3 styrene oxide 
• 1504-78-5 3-phenylquinoxaline-2(1H)-one 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 93-56-1 phenylethane 1,2-diol 
• 70-11-1 α-bromoacetophenone 
• 98-86-2 acetophenone 
• 28203-05-6 dimethoxy-2,2 phenyl-2 ethanol-1 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 5495-09-0 3-phenyl-1,2-dihydro-2H-quinoxaline 
• 37167-62-7 bromo-phenyl-acetic acid methyl ester 
• 5021-43-2 2-phenylquinoxaline 

Downstream Products

• 5021-43-2 2-phenylquinoxaline 
• 1425037-10-0 1-(3-trifluoromethoxy)benzyl-3-phenyl-1,2,3,4-tetrahydroquinoxaline 
• 1222843-82-4 (R)-2-phenyl-1,2,3,4-tetrahydroquinoxaline 
• 1203948-11-1 (S)-2-phenyl-1,2,3,4-tetrahydroquinoxaline 
• 1425037-11-1 (R)-3-((S)-4-(3-trifluoromethoxybenzyl)-2-phenyl-3,4-dihydroquinoxalin-1(2H)-yl)-1,1,1-trifluoropropan-2-ol 
• 1425037-09-7 (R)-3-((R)-4-(3-trifluoromethoxybenzyl)-2-phenyl-3,4-dihydroquinoxalin-1(2H)-yl)-1,1,1-trifluoropropan-2-ol 
• 1425037-13-3 (R)-3-((R)-4-(3-trifluoromethoxybenzyl)-2-phenyl-3,4-dihydroquinoxalin-1(2H)-yl)-1,1,1-trifluoropropan-2-ol 
• 1425037-12-2 (R)-3-((R)-4-(3-trifluoromethoxybenzyl)-2-phenyl-3,4-dihydroquinoxalin-1(2H)-yl)-1,1,1-trifluoropropan-2-ol 

Relevant articles and documents

Kinetic Resolution by Lithiation: Highly Enantioselective Synthesis of Substituted Dihydrobenzoxazines and Tetrahydroquinoxalines

Kinetic resolution provided a highly enantioselective method to access a range of 3-aryl-3,4-dihydro-2H-1,4-benzoxazines using n-butyllithium and the chiral ligand sparteine. The enantioenrichment remained high on removing the tert-butoxycarbonyl (Boc) protecting group. The intermediate organolithium undergoes ring opening to an enamine. The kinetic resolution was extended to give enantiomerically enriched substituted 1,2,3,4-tetrahydroquinoxalines and was applied to the synthesis of an analogue of the antibiotic levofloxacin that was screened for its activity against the human pathogen Streptococcus pneumoniae.

Preparation method of tetrahydroquinoxaline compound

The invention discloses a preparation method of a tetrahydroquinoxaline compound. The method comprises the following steps: 1) by using quinoxaline as a starting raw material, adding quinoxaline, a catalyst and borane into a reaction tube, adding a certai

Tetrabutylammonium Bromide-Catalyzed Transfer Hydrogenation of Quinoxaline with HBpin as a Hydrogen Source

A metal-free environmentally benign, simple, and efficient transfer hydrogenation process of quinoxaline has been developed using the HBpin reagent as a hydrogen source. This reaction is compatible with a variety of quinoxalines offering the desired tetrahydroquinoxalines in moderate-to-excellent yields with Bu4NBr as a noncorrosive and low-cost catalyst.

A quantum-chemical approach to develop tetrahydroquinoxaline as potent ferroptosis inhibitors

Ferroptosis is a recently characterized form of regulated necrosis with the iron-dependent accumulation of (phospho)lipid hydroperoxides (LOOH). It has attracted considerable attention for its putative involvement in diverse pathophysiological processes, such as cardiovascular disease and neurodegeneration. Here we describe the discovery of tetrahydroquinoxaline, a novel scaffold of ferroptosis inhibitors based on quantum chemistry methods. Tetrahydroquinoxaline deviates showed very good inhibition of ferroptosis, while being non cytotoxic for human cancer cells. And, the advantage of them is their small molecular weight (MW. = 148 Da) that can be coupled with other drugs to form multi-target drugs to better meet the treatment of complicated diseases.

Hydrogenation or Dehydrogenation of N-Containing Heterocycles Catalyzed by a Single Manganese Complex

A highly chemoselective base-metal catalyzed hydrogenation and acceptorless dehydrogenation of N-heterocycles is presented. A well-defined Mn complex operates at low catalyst loading (as low as 2 mol %) and under mild reaction conditions. The described catalytic system tolerates various functional groups, and the corresponding reduced heterocycles can be obtained in high yields. Experimental studies indicate a metal-ligand cooperative catalysis mechanism.

HMPA-catalyzed transfer hydrogenation of 3-carbonyl pyridines and other N-heteroarenes with trichlorosilane

A method for the HMPA (hexamethylphosphoric triamide)-catalyzed metal-freetransfer hydrogenation of pyridines has been developed. The functional group tolerance of the existing reaction conditions provides easy access to various piperidines with ester or ketone groups at the C-3 site. The suitability of this method for the reduction of other N-heteroarenes has also been demonstrated. Thirty-three examples of different substrates have been reduced to designed products with 45–96% yields.

Stereoconvergent, Redox-Neutral Access to Tetrahydroquinoxalines through Relay Epoxide Opening/Amination of Alcohols

We present an economical catalytic procedure to convert readily available 1,2-diaminobenzenes and terminal epoxides into valuable 1,2,3,4-tetrahydroquinoxalines in a highly enantioselective fashion. This procedure operates through relay zinc and iridium catalysis, and achieves redox-neutral and stereoconvergent production of valuable chiral heterocycles from racemic starting materials with water as the only side product. The use of commercially available reagents and catalysts and a convenient procedure also make this catalytic method attractive for practical application.

B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane

The first B(C6F5)3-catalyzed deoxygenative reduction of amides into the corresponding amines with readily accessible and stable ammonia borane (AB) as a reducing agent under mild reaction conditions is reported. This metal-free protocol provides facile access to a wide range of structurally diverse amine products in good to excellent yields, and various functional groups including those that are reduction-sensitive were well tolerated. This new method is also applicable to chiral amide substrates without erosion of the enantiomeric purity. The role of BF3 ? OEt2 co-catalyst in this reaction is to activate the amide carbonyl group via the in situ formation of an amide-boron adduct. (Figure presented.).

Tetrahydroquinoxaline compound, and preparation method and application thereof

The invention provides a tetrahydroquinoxaline compound, and a preparation method and application thereof. The chemical structure is shown in a formula I: the tetrahydroquinoxaline compound has good cell ferroptosis inhibition activity, and can be used fo

Cu-catalyzed reduction of azaarenes and nitroaromatics with diboronic acid as reductant

A ligand-free copper-catalyzed reduction of azaarenes with diboronic acid as reductant in an aprotic solvent under mild conditions has been developed. Most interestingly, the nitroazaarenes could be reduced exclusively to give the corresponding amines without touching the azaarene moieties. Furthermore, the reductive amination of aromatic nitro compounds and aromatic aldehydes has also been realized. A series of hydrogenated azaarenes and secondary amines were obtained with good functional group tolerance.