873404-52-5

Basic information

• Product Name: 3-Benzyl-3,4-dihydroisoquinolin-1(2H)-one
• Synonyms: 3-Benzyl-3,4-dihydroisoquinolin-1(2H)-one
• CAS NO: 873404-52-5
• Molecular Formula: C₁₆H₁₅NO
• Molecular Weight: 237.2964
• Mol File: 873404-52-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Benzyl-3,4-dihydroisoquinolin-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Benzyl-3,4-dihydroisoquinolin-1(2H)-one(873404-52-5)
• EPA Substance Registry System: 3-Benzyl-3,4-dihydroisoquinolin-1(2H)-one(873404-52-5)

Safety Data

• Hazardous Substances Data: 873404-52-5(Hazardous Substances Data)

Upstream product

• 495-18-1 Benzohydroxamic acid 
• 300-57-2 allylbenzene 
• 61650-22-4 N-(pivaloyloxy)benzamide 
• 4275-43-8 1-benzyl-2-phenylethylamine 
• 253177-44-5 1-benzyl-2-phenyl-ethyl isocyanate 

Downstream Products

• 872788-04-0 3-benzyl-1-chloro-isoquinoline 
• 787-46-2 3-benzyl-isoquinolin-1-ol 

Relevant articles and documents

Ligand design for Rh(iii)-catalyzed C-H activation: An unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones

We report the regioselective synthesis of dihydroisoquinolones from aliphatic alkenes and O-pivaloyl benzhydroxamic acids mediated by a Rh(iii) precatalyst bearing sterically bulky substituents. While the prototypical Cp ligand provides product with low s

Rhodium(III)-catalyzed heterocycle synthesis using an internal oxidant: Improved reactivity and mechanistic studies

Directing groups that can act as internal oxidants have recently been shown to be beneficial in metal-catalyzed heterocycle syntheses that undergo C-H functionalization. Pursuant to the rhodium(III)-catalyzed redox-neutral isoquinolone synthesis that we recently reported, we present in this article the development of a more reactive internal oxidant/directing group that can promote the formation of a wide variety of isoquinolones at room temperature while employing low catalyst loadings (0.5 mol %). In contrast to previously reported oxidative rhodium(III)-catalyzed heterocycle syntheses, the new conditions allow for the first time the use of terminal alkynes. Also, it is shown that the use of alkenes, including ethylene, instead of alkynes leads to the room temperature formation of 3,4-dihydroisoquinolones. Mechanistic investigations of this new system point to a change in the turnover limiting step of the catalytic cycle relative to the previously reported conditions. Concerted metalation-deprotonation (CMD) is now proposed to be the turnover limiting step. In addition, DFT calculations conducted on this system agree with a stepwise C-N bond reductive elimination/N-O bond oxidative addition mechanism to afford the desired heterocycle. Concepts highlighted by the calculations were found to be consistent with experimental results.