1229227-22-8

Basic information

• Product Name: 4-nitrophenyl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
• Synonyms: 4-nitrophenyl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS NO: 1229227-22-8
• Molecular Weight: 374.396
• Mol File: 1229227-22-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-nitrophenyl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrophenyl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate(1229227-22-8)
• EPA Substance Registry System: 4-nitrophenyl (1S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate(1229227-22-8)

Safety Data

• Hazardous Substances Data: 1229227-22-8(Hazardous Substances Data)

Upstream product

• 22990-19-8 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 17507-05-0 1-phenyl-1,4-dihydro-3(2H)-isoquinolinone 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 

Downstream Products

• 242478-37-1 solifenacin 

Relevant articles and documents

Engineering an enantioselective amine oxidase for the synthesis of pharmaceutical building blocks and alkaloid natural products

The development of cost-effective and sustainable catalytic methods for the production of enantiomerically pure chiral amines is a key challenge facing the pharmaceutical and fine chemical industries. This challenge is highlighted by the estimate that 40-45% of drug candidates contain a chiral amine, fueling a demand for broadly applicable synthetic methods that deliver target structures in high yield and enantiomeric excess. Herein we describe the development and application of a "toolbox" of monoamine oxidase variants from Aspergillus niger (MAO-N) which display remarkable substrate scope and tolerance for sterically demanding motifs, including a new variant, which exhibits high activity and enantioselectivity toward substrates containing the aminodiphenylmethane (benzhydrylamine) template. By combining rational structure-guided engineering with high-throughput screening, it has been possible to expand the substrate scope of MAO-N to accommodate amine substrates containing bulky aryl substituents. These engineered MAO-N biocatalysts have been applied in deracemization reactions for the efficient asymmetric synthesis of the generic active pharmaceutical ingredients Solifenacin and Levocetirizine as well as the natural products (R)-coniine, (R)-eleagnine, and (R)-leptaflorine. We also report a novel MAO-N mediated asymmetric oxidative Pictet-Spengler approach to the synthesis of (R)-harmicine.

Enantioselective synthesis of 1-aryltetrahydroisoquinolines

(Figure presented) 1-Aryltetrahydroisoquinolines (1-arylTHIQs) are important structural motifs in many alkaloids and biologically active compounds. Ligand 2a promotes the enantioselective addition of arylzinc reagents to 3,4-dihydroisoquinoline N-oxide to