6772-73-2

Basic information

• Product Name: 1,4-dihydro-2-(phenylmethyl)-3(2H)-isoquinolinone
• Synonyms: 1,4-dihydro-2-(phenylmethyl)-3(2H)-isoquinolinone
• CAS NO: 6772-73-2
• Molecular Weight: 237.301
• Mol File: 6772-73-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,4-dihydro-2-(phenylmethyl)-3(2H)-isoquinolinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-dihydro-2-(phenylmethyl)-3(2H)-isoquinolinone(6772-73-2)
• EPA Substance Registry System: 1,4-dihydro-2-(phenylmethyl)-3(2H)-isoquinolinone(6772-73-2)

Safety Data

• Hazardous Substances Data: 6772-73-2(Hazardous Substances Data)

Usage

Classification

Isoquinoline alkaloid

Natural source

Opium poppy

Primary use

Smooth muscle relaxation

Mechanism of action

Inhibition of phosphodiesterase enzyme

Effect on cAMP levels

Increase

Tissue response

Smooth muscle tissue relaxation

Applications

Treatment of erectile dysfunction, peripheral vascular disease, and cerebral vasospasm

Additional investigations

Potential anti-cancer and neuroprotective effects

Upstream product

• 63969-83-5 2-formylphenylacetic acid methyl ester 
• 100-46-9 benzylamine 
• 103-49-1 dibenzylamine 
• 828-51-3 1-Adamantanecarboxylic acid 
• 2567-51-3 2-chloro-N,N-bis(phenylmethyl)acetamide 
• 24331-94-0 1,4-dihydro-3(2H)-isoquinolinone 
• 100-39-0 benzyl bromide 
• 4385-35-7 isochroman-3-one 

Relevant articles and documents

Synthetic approaches to N- and 4-substituted 1,4-dihydro-3(2H)-isoquinolinone derivatives

Reaction of methyl-2-(2-formylphenyl)acetate with primary amines in a reductive amination/cyclisation process resulted in N-substituted 1,4-dihydro-3(2H)-isoquinolinones. With H2NCH2R sodium borohyride is a suitable reductant (11 examples), but H2NCHR1R2 required a transfer hydrogenation using ammonium formate catalysed by palladium on carbon (9 examples). 4-Substituted-1,4-dihydro-3(2H)-isoquinolinones were synthesised by deprotonation (n-butyllithium) and addition of R3CH2Br (12 examples with R3 = alkyl, Ar, CH[dbnd]CH2, C[tbnd]CH). Modest diastereoselectivity was achieved with 1,4-dihydro-3(2H)-isoquinolinones derived from H2NCHMeR2 [R2 = (η5-C5H4)Co(η4-C4Ph4) - max. dr = 1.9 : 1], but use of H2NCHMeFc (Fc = ferrocenyl) provided a new method of 1,4-dihydro-3(2H)-isoquinolinone N-deprotection with formic acid.

Access to β-lactams by enantioselective palladium(0)-catalyzed C(sp3)-H alkylation

β-Lactams are very important structural motifs because of their broad biological activities as well as their propensity to engage in ring-opening reactions. Transition-metal-catalyzed C-H functionalizations have emerged as strategy enabling yet uncommon h

Synthetic approaches to 2-substituted 1-oxo- and 3-oxotetrahydroisoquinolines

2-Substituted homophthalimides 2a-c were reduced regioselectively with sodium borohydride to carbinol-lactam intermediates 3a-c, which were dehydrated, followed by hydrogenation, to give 1-oxotetrahydroisoquinolines or 3,4-dihydroisoquinolin-1(2H)ones 5a-c. The isomeric 3-oxo-tetrahydroisoquinolines or 1,4-dihydroisoquinolin-3(2H)-ones 8a-i were obtained in satisfactory yields via heating 3-isochromanone (6) with the corresponding amines 7a-i in the presence of aluminum chloride.