350249-64-8

Basic information

• Product Name: 2-[(S)-2-benzyl-1-hydroxyethyl]-1-oxo-1,2,3,4-tetrahydrobenzo[1,3-b]naphthyridine
• CAS NO: 350249-64-8
• Molecular Weight: 332.402
• Mol File: 350249-64-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-[(S)-2-benzyl-1-hydroxyethyl]-1-oxo-1,2,3,4-tetrahydrobenzo[1,3-b]naphthyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(S)-2-benzyl-1-hydroxyethyl]-1-oxo-1,2,3,4-tetrahydrobenzo[1,3-b]naphthyridine(350249-64-8)
• EPA Substance Registry System: 2-[(S)-2-benzyl-1-hydroxyethyl]-1-oxo-1,2,3,4-tetrahydrobenzo[1,3-b]naphthyridine(350249-64-8)

Safety Data

• Hazardous Substances Data: 350249-64-8(Hazardous Substances Data)

Upstream product

• 350249-63-7 2-[2-((S)-1-Hydroxymethyl-2-phenyl-ethylamino)-ethyl]-quinoline-3-carbonitrile 
• 34846-64-5 3-cyanoquinoline 
• 350249-62-6 2-ethynylquinoline-3-carbonitrile 
• 63124-13-0 quinoline-3-carbonitrile N-oxide 
• 95104-21-5 2-chloroquinoline-3-carbonitrile 

Relevant articles and documents

Stable annelated chiral NADH models with a rigidified amide part in the quinoline series: Synthesis, reactivity and grafting on a Merrifield resin

The synthesis of new chiral nicotinamide adenine dinucleotide hydrogenated models derived from quinoline is described. Using a biomimetic approach, the out-of-plane positioning of the amide carbonyl was obtained by involving the chiral auxiliary in a lactam structure. It is shown that electron-donating groups on the benzene ring of the quinoline structure are necessary to obtain high chemical yields during the reduction of methyl benzoylformate. An interesting variation of the enantioselectivity as a function of magnesium ion concentration has been observed. Under the best conditions, methyl mandelate was obtained in up to 95% ee (R). To facilitate the recycling of these models, grafting of reagent 4 on a Merrifield resin has been developed. The resulting polymer-supported reagent 4 was tested in the asymmetric reduction of methyl benzoylformate.