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
• Article Data: 6

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

1,4-Dihydro-1-phenyl-3(2H)-isoquinolinone is used as a reagent in the synthesis of a series of 1-aryl-3-dimethylamino-1,4-dihydroisoquinolines which display anti-arthritic activity. Also used as a reagent in the synthesis of 1-aryl-1,4-dihydro-3(2H)-isoquinolinones which have potential antiserotoninergic activity.

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

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

Downstream Products

• 82255-69-4 1-Phenyl-4-methyl-3-(2H)isoquinolinone 
• 7651-81-2 3-isoquinolinol 
• 78634-19-2 (E)-4-(hydroxyimino)-1-phenyl-1,4-dihydro-3(2H)-isoquinolinone 
• 78634-18-1 (Z)-4-(hydroxyimino)-1-phenyl-1,4-dihydro-3(2H)-isoquinolinone 
• 120298-54-6 4,4-Dichloro-1-phenyl-1,4-dihydro-3(2H)-isoquinolinone 
• 120285-06-5 3,4-Dibromo-1-phenylisoquinoline 
• 120285-00-9 3,4-Dichloro-1-phenylisoquinoline 
• 130042-79-4 (+/-)-1,4-dihydro-1-phenylisoquinolin-3(2H)-thione 
• 6637-53-2 3-hydroxy-3-phenyl-2,3-dihydro-isoindol-1-one 
• 143266-01-7 3-ethoxy-1,4-dihydro-1-phenylisoquinoline 
• 92462-16-3 1-phenyl-2-tritylcarbamoyl-1,4-dihydro-3(2H)-isoquinolinone 
• 133387-71-0 1-phenyl-2-(2-chloroethylcarbamoyl)-1,4-dihydro-3(2H)-isoquinolinone 
• 69135-54-2 1-phenyl-2-carbamoyl-1,4-dihydro-3(2H)-isoquinolinone 
• 869884-00-4 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline tartarate 

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.

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.

Substituted 1,4-dihydro-1-phenylisoquinolin-3(2H)-ones as inhibitors of cyclic nucleotide phosphodiesterases from dog heart

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