253308-74-6

Basic information

• Product Name: (S)-(-)-3-phenyl-3,4-dihydro-2H-isoquinolin-1-one
• Synonyms: (S)-(-)-3-phenyl-3,4-dihydro-2H-isoquinolin-1-one
• CAS NO: 253308-74-6
• Molecular Weight: 223.274
• Mol File: 253308-74-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (S)-(-)-3-phenyl-3,4-dihydro-2H-isoquinolin-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-3-phenyl-3,4-dihydro-2H-isoquinolin-1-one(253308-74-6)
• EPA Substance Registry System: (S)-(-)-3-phenyl-3,4-dihydro-2H-isoquinolin-1-one(253308-74-6)

Safety Data

• Hazardous Substances Data: 253308-74-6(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 61650-22-4 N-(pivaloyloxy)benzamide 
• 1821-34-7 N-chlorobenzamide 
• 1293990-69-8 N-((tert-butoxycarbonyl)oxy)benzamide 
• 88000-67-3 tert-butyl benzoylimidocarboxylate 
• 158109-78-5 (R,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 2728-04-3 N,N-diethyl-ortho-toluamide 
• 253308-73-5 (S)-(+)-N,N-diethyl-2-(2-amino-2-phenylethyl)benzamide 
• 1393378-82-9 (S)-2-((S)-2-methoxymethylpyrrolidin-1-yl)-3-phenyl-3,4-dihydro-2H-isoquinolin-1-one 

Relevant articles and documents

Chiral Cyclopentadienyl Cobalt(III) Complexes Enable Highly Enantioselective 3d-Metal-Catalyzed C-H Functionalizations

The synthesis of a set of cobalt(III)-complexes equipped with trisubstituted chiral cyclopentadienyl ligands is reported, and their steric and electronic parameters are mapped. The application potential of these complexes for asymmetric C-H functionalizations with 3d-metals is shown by the synthesis of dihydroisoquinolones from N-chlorobenzamides with a broad range of alkenes. The transformation proceeds with excellent enantioselectivities of up to 99.5:0.5 er and high regioselectivities. The observed values outperform the best rhodium(III)-based methods for this reaction type. Moreover, challenging substrates such as alkyl alkenes also react with high regio- and enantioselectivities.

Mild complexation protocol for chiral CpxRh and Ir complexes suitable for: In situ catalysis

A practical complexation method for chiral cyclopentadienyl (Cpx) iridium and rhodium complexes is described. The procedure uses the free CpxH with stable and commercially available rhodium(i) and iridium(i) salts without base or additive. The conditions are mild and do not require the exclusion of air and moisture. A salient feature is the suitability for in situ complexations enhancing the user-friendliness of Cpx ligands in asymmetric catalysis. DFT-calculations confirm an intramolecular proton abstraction pathway by either the bound acetate or methoxide. Furthermore, the superior facial selectivity of the proton abstraction step enabled the development of TMS-containing trisubstituted Cpx ligands which display improved enantioselectivities for the benchmarking dihydroisoquinolone synthesis.

Stereoselective photoinduced electrocyclic ring closure of aromatic enehydrazides. Asymmetric synthesis of 3-aryl dihydroisoquinolones and tetrahydroisoquinolines

A flexible route for the stereoselective synthesis of a variety of 3-aryl dihydroisoquinolones and tetrahydroisoquinolines has been developed. The key step is a diastereoselective photoinduced 6π-electrocyclic ring closure of enantiopure aromatic enehydrazides via a 1,4-remote asymmetric induction. N-N bond cleavage to release the chiral appendage from the preliminary annulated compounds and/or concomitant reduction of the lactam carbonyl group completed the synthesis of the title compounds.