17507-05-0

Basic information

• Product Name: 1-phenyl-1,2-dihydroisoquinolin-3(4H)-one
• Synonyms: 1,4-DIHYDRO-1-PHENYL-3(2H)-ISOQUINOLINONE;1-Phenyl-1,4-dihydroisoquinolin-3(2H)-one;1-Phenyl-1,2-dihydroisoquinolin-3(4H)
• CAS NO: 17507-05-0
• Molecular Formula: C₁₅H₁₃NO
• Molecular Weight: 223.26982
• Mol File: 17507-05-0.mol

Chemical Properties

• Melting Point: 164-165 °C
• Boiling Point: 444.4°Cat760mmHg
• Flash Point: 266.4°C
• Appearance: /
• Density: 1.156g/cm³
• Vapor Pressure: 4.29E-08mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 15.63±0.40(Predicted)
• CAS DataBase Reference: 1-phenyl-1,2-dihydroisoquinolin-3(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenyl-1,2-dihydroisoquinolin-3(4H)-one(17507-05-0)
• EPA Substance Registry System: 1-phenyl-1,2-dihydroisoquinolin-3(4H)-one(17507-05-0)

Safety Data

• Hazardous Substances Data: 17507-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenyl-1,2-dihydroisoquinolin-3(4H)-one is used as a reagent for the synthesis of a series of 1-aryl-3-dimethylamino-1,4-dihydroisoquinolines, which exhibit anti-arthritic activity. Its role in the development of these compounds makes it a valuable component in the pharmaceutical industry, particularly for the treatment of arthritis-related conditions.
Additionally, 1-Phenyl-1,2-dihydroisoquinolin-3(4H)-one is utilized as a reagent in the synthesis of 1-aryl-1,4-dihydro-3(2H)-isoquinolinones. These synthesized compounds have potential antiserotoninergic activity, which can be beneficial in the development of medications targeting serotonin-related disorders.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 30, p. 381, 1993 DOI: 10.1002/jhet.5570300216

InChI:InChI=1/C15H13NO/c17-14-10-12-8-4-5-9-13(12)15(16-14)11-6-2-1-3-7-11/h1-9,15H,10H2,(H,16,17)

Upstream product

• 140-29-4 phenylacetonitrile 
• 100-52-7 benzaldehyde 
• 103-81-1 Benzeneacetamide 
• 151832-39-2 N-(α-benzotriazol-1-ylmethyl)phenylacetamide 
• 7651-81-2 3-isoquinolinol 
• 71-43-2 benzene 

Downstream Products

• 50845-51-7 4-benzyl-1-phenyl-3-(2H)isoquinolinone 
• 24331-94-0 1,4-dihydro-3(2H)-isoquinolinone 
• 102879-33-4 2,3,5,6,7,8-Hexahydroisoquinol-3-one 
• 143266-10-8 3-ethoxy-4-methyl-1-phenyl-1H-2-benzazepine 
• 143266-09-5 3-ethoxy-4-methyl-1-phenyl-5H-2-benzazepine 
• 143265-99-0 3-ethoxy-1,4-dihydro-4-methyl-1-phenylisoquinoline 
• 143266-14-2 4,5-dimethyl-3-ethoxy-1-phenyl-1H-2-benzazepine 
• 143266-02-8 3-ethoxy-1,4-dihydro-4-hydroxymethyl-4-methyl-1-phenylisoquinoline 
• 143266-08-4 3-ethoxy-1,4-dihydro-4-(1-hydroxyethyl)-4-methyl-1-phenylisoquinoline 
• 143266-04-0 4-acetyl-3-ethoxy-1,4-dihydro-4-methyl-1-phenylisoquinoline 
• 143266-12-0 4-benzyl-3-ethoxy-4-methyl-1-phenyl-1H-2-benzazepine 
• 143266-11-9 4-benzyl-3-ethoxy-4-methyl-1-phenyl-5H-2-benzazepine 
• 143266-00-6 4-benzyl-3-ethoxy-1,4-dihydro-1-phenylisoquinoline 
• 143266-03-9 4-benzyl-3-ethoxy-1,4-dihydro-4-hydroxymethyl-1-phenylisoquinoline 

Relevant articles and documents

A convenient synthesis of 1-substituted 1,4-dihydroisoquinolin-3-ones

A number of isoquinolin-3-ones have been obtained in fair to good yields by reaction of phenylacetonitrile with carbonyl compounds in PPA.

Superacidic activation of 1- and 3-isoquinolinols and their electrophilic reactions

Isomeric 1- and 3-isoquinolinols (11 and 12) when activated in CF3SO3H-SbF5 acid system undergo selective ionic hydrogenation with cyclohexane to give 5,6,7,8-tetrahydro-1(2H)- and 5,6,7,8-tetrahydro-3(2H)-isoquinolinones (22 and 27). Under the influence of aluminum chloride similar products were also obtained along with 3,4-dihydro-1(2H)- and 1,4-dihydro-3(2H)-isoquinolinones (23 and 28), respectively. Compounds 11 and 12 also condense with benzene in the presence of aluminum halides, under mild conditions, to give 3,4-dihydro-3-phenyl-1(2H)- and 1,4-dihydro-1-phenyl-3(2H)-isoquinolinones (24 and 29), respectively. Prolonged reaction time or catalysis under strongly acidic HBr-AlBr3 provides an alternative reaction pathway to yield 5,6-dihydro-6,8-diphenyl-1(2H)- and 5,6,7,8-tetrahydro-6,8-diphenyl-3(2H)-isoquinolinones (25 and 30), respectively. Products 24 and 29 were also found to revert back to 11 and 12 in the presence of aluminum halides in o-dichlorobenzene. The mechanism of these intriguing reactions, which involves superelectrophilic dicationic intermediates, is discussed.

1-Aryl-1,4-dihydro-3(2H)-isoquinolinones: Two modes of interaction with 5-HT(1A) receptors

Two series of 1-aryl-1,4-dihydro-3(2H)-isoquinoline derivatives were synthesized, and their in vitro and in vivo properties at 5-HT(1A) and 5- HT(2A) receptors were evaluated. In was shown that series a, containing a 1- (m-chlophenyl)piperazine fragment, interacts with 5-HT(1A) receptors in two different modes: as an ordinary 4-substituted 1-arylpiperazine and as a pseudo one. Series b, with a 1,2,3,4-tetrahydroisoquinoline moiety, binds to the receptor thanks to a pseudo 1-arylpiperazine fragment. Regardless of the mode of interaction, both those series demonstrated 5-HT(1A) receptor antagonistic properties in animal models. Different in vivo properties of 2b, due to a 7-methoxy substituent, indicate that the isoquinolinone portion also interacts with 5-HT(1A) receptors.

Novel Routes to 1-Aryl-1,4-dihydro-3(2H)-isoquinolinones and 2-Substituted or 2,3-Disubstituted Benzofurans by Intramolecular Cyclizations

N-(α-Benzotriazolylalkyl)arylacetamides, readily available from an arylacetamide, an aldehyde and benzotriazole, undergo intramolecular cyclization under acidic conditions to give 1-aryl-1,4-dihydro-3(2H)-isoquinolinones in good to excellent yields.Similarly, 2-(benzotriazol-1-yl)-2-(o-hydroxyphenyl)ethanols, obtained by lithiation of 2-(benzotriazol-1-ylmethyl)phenols followed by quenching with aldehydes or ketones, eliminate a molecule of water and a molecule of benzotriazole yielding 2-substituted and 2,3-disubstituted benzofurans.