33273-99-3

Basic information

• Product Name: 2-Quinolinecarboxaldehyde, 4-phenyl-
• Synonyms: 4-phenyl-2-quinolinecarbaldehyde;4-phenyl-quinoline-2-carbaldehyde;4-phenyl-2-quinolyl-carboxaldehyde;2-Quinolinecarboxaldehyde,4-phenyl;4-Phenylchinolin-2-carboxaldehyd;2-Formyl-4-phenyl-chinolin;4-phenyl-2-quinolinecarboxaldehyde
• CAS NO: 33273-99-3
• Molecular Formula: C16H11NO
• Molecular Weight: 233.269
• Mol File: 33273-99-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Quinolinecarboxaldehyde, 4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Quinolinecarboxaldehyde, 4-phenyl-(33273-99-3)
• EPA Substance Registry System: 2-Quinolinecarboxaldehyde, 4-phenyl-(33273-99-3)

Safety Data

• Hazardous Substances Data: 33273-99-3(Hazardous Substances Data)

Upstream product

• 1721-92-2 2-methyl-4-phenylquinoline 

Downstream Products

• 1426679-18-6 4'-phenyl-2-tosyl-1,2,3,3',4',9-hexahydro-1'H-spiro[pyrido[3,4-b]indole-4,2'-quinoline] 
• 1426679-02-8 C₂₅H₂₁N₃ 
• 1426678-91-2 N-((1H-indol-2-yl)methyl)-4-methyl-N-((4-phenylquinolin-2-yl)methyl)benzenesulfonamide 
• 24644-35-7 2-benzothiazol-2-yl-4-phenyl-quinoline 

Relevant articles and documents

Asymmetric 1,3-dipolar cycloaddition reactions of nitrile oxides catalyzed by chiral binaphthyldiimine-Ni(II) complexes

Asymmetric cycloaddition reactions between several nitrile oxides and 3-(2-alkenoyl)-2-oxazolidinones and 2-(2-alkenoyl)-3-pyrazolidinone derivatives were carried out in the presence of chiral binaphthyldiimine (BINIM)-Ni(II) complexes as catalysts. Using (tf)-BENM-4(3,5-xylyl)-2QN-Ni(II) complex (30 mol %), good regioselectivity (4-Me/5-Me = 85:15) along with high enantioselectivity (96% ee) of the 4-Me adduct were obtained for the reaction between isolable 2,4,6-trimethylbenzonitrile oxide and 3-crotonoyl-5,5-dimethyl-2-oxazolidinone. Substituted and unsubstituted benzonitrile oxides and aliphatic nitrile oxides, which were generated from the corresponding hydroximoyl chloride in the presence of MS 4A, were reacted with 3-crotonoyl-5,5-dimethyl-2-oxazolidinone, 5,5-dimethyl-3-(2-pentenoyl)-2-oxazolidinone, 5,5-dimethy-3-[3-(ethoxycarbonyl) propenoyl]-2-oxazolidinone, 1-benzyl-2-crotonoyl-5,5-dimethyl-3-pyrazolidinone, and 1-ben-zyl-2-[3-(ethoxycarbonyl)propenoyl]-5,5-dimethy-3-pyrazolidinone in the presence of (K)-BENM-4Ph-2QN-Ni(II) or (tf)-BENM-4(3,5-xylyl)-2QN-Ni(II) complexes (10-30 mol %) as catalysts to give the corresponding cycloadducts in high yields, with high regioselectively (4-R/5-R = 85:15-99:1) and with moderate to high enantioselectivities (42-95% ee) of the 4-R adducts. Higher enantioselectivities and regioselectivities were obtained for the reactions using pyrazolidinone derivatives as the dipolarophiles. For the cycloadditions of 2-(2-alkenoyl)-1-benzyl-5,5-dimethyl-3-pyrazolidinones catalyzed by (tf)-BENM-4(3,5-xylyl)-2QN-Ni(II) complex (30 mol %), the enantioselectivity varied from 75% to 95% ee. The reactions between several nitrile oxides and 2-acryloyl-1-benzyl-5,5-dimethyl-3-pyrazolidinone in the presence of (R)-BINIM-4(3,5-xylyl)-2QN-Ni(II) complex (10 mol %) resulted in enantioselectivities (79-91% ee) that exceed those of previously reported enantioselective cycloadditions of acrylic acid derivatives. Furthermore, studies using a molecular modeling program using PM3 calculations were carried out to gain insight into the mechanisms of the asymmetric induction. 2009 American Chemical Society.