trans-N-Tosyl-3-benzylidene-2,3-dihydro-4-quinolone

Base Information

• Chemical Name: trans-N-Tosyl-3-benzylidene-2,3-dihydro-4-quinolone
• CAS No.: 76263-65-5
• Molecular Formula: C23H19 N O3 S
• Molecular Weight: 389.475
• Hs Code.: 2935009090
• Wikidata: Q76388000
• Mol file: 76263-65-5.mol

Synonyms:trans-N-Tosyl-3-benzylidene-2,3-dihydro-4-quinolone;BRN 4559257;76263-65-5;(3E)-3-benzylidene-1-(4-methylphenyl)sulfonyl-2H-quinolin-4-one;(E)-1-((4-Methylphenyl)sulfonyl)-3-(phenylmethylene)-2,3-dihydro-4(1H)-quinolinone;4(1H)-Quinolinone, 2,3-dihydro-1-((4-methylphenyl)sulfonyl)-3-(phenylmethylene)-, (E)-;C23H19NO3S;C23-H19-N-O3-S;LS-142749;1-((4-methylphenyl)sulfonyl)-3-(phenylmethylene)-2,3-dihydro-4(1h)-quinolinone

Chemical Property of trans-N-Tosyl-3-benzylidene-2,3-dihydro-4-quinolone

Chemical Property:

• Vapor Pressure: 1.1E-13mmHg at 25°C
• Boiling Point: 585.3°C at 760 mmHg
• Flash Point: 307.8°C
• PSA: 62.83000
• Density: 1.319g/cm³
• LogP: 5.61600
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 389.10856464
• Heavy Atom Count: 28
• Complexity: 694

Purity/Quality:

99%min ^*data from raw suppliers

(E)-1-((4-METHYLPHENYL)SULFONYL)-3-(PHENYLMETHYLENE)-2,3-DIHYDRO-4-(1H)QUINOLINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2CC(=CC3=CC=CC=C3)C(=O)C4=CC=CC=C42
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C/C(=C\C3=CC=CC=C3)/C(=O)C4=CC=CC=C42

Technology Process of trans-N-Tosyl-3-benzylidene-2,3-dihydro-4-quinolone

There total 19 articles about trans-N-Tosyl-3-benzylidene-2,3-dihydro-4-quinolone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

1-tosyl-2,3-dihydroquinolin-4(1H)-one (14278-37-6) + benzaldehyde (100-52-7) → (E)-3-[1-(phenyl)-methylidene]-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-quinolin-4-one (76263-65-5)

Guidance literature:

With sodium methylate; In methanol; for 4h; Ambient temperature;

Reference yield: 90.0%

benzaldehyde (100-52-7) + N-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-4-methyl-benzenesulfonamide (665033-49-8) → (E)-3-[1-(phenyl)-methylidene]-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-quinolin-4-one (76263-65-5)

Guidance literature:

With trifluorormethanesulfonic acid; In 1,4-dioxane; Sealed tube; Reflux;

Reference yield: 76.0%

N-[2-(2-bromobenzoyl)-1-phenylallyl]-4-methylbenzenesulfonamide → (E)-3-[1-(phenyl)-methylidene]-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-quinolin-4-one (76263-65-5)

Guidance literature:

With copper(l) iodide; cesium acetate; In acetonitrile; at 82 ℃; for 12h; Reagent/catalyst; Solvent; Temperature;

DOI:10.1002/adsc.201801490

upstream raw materials:

1-tosyl-2,3-dihydroquinolin-4(1H)-one

benzaldehyde

ethyl 3-phenylaminopropionate

N-((4-methylphenyl)sulfonyl)-N-phenyl-beta-alanine

Downstream raw materials:

2-acetyl-3-phenyl-5-tosyl-3,3a,4,5-tetrahydropyrazolo<4,3-c>quinoline

C₂₃H₁₉NO₄S

3-phenyl-2H-pyrazolo<4,3-c>quinoline

2,3-diphenyl-2H-pyrazolo<4,3-c>quinoline

Refernces

• 1、 Raga, Esther,Escolano, Marcos,Torres, Javier,Rabasa-Alca?iz, Fernando,Sánchez-Roselló, María,del Pozo, Carlos. "Domino Synthesis of 3-Alkyliden-2,3-Dihydro-4-Quinolones". . p. 1102 - 1107. Retrieved 2019/01/30.
• 2、 Biju, Akkattu T.,Wurz, Nathalie E.,Glorius, Frank. "N-heterocyclic carbene-catalyzed cascade reaction involving the hydroacylation of unactivated alkynes". supporting information; experimental part. p. 5970 - 5971. Retrieved 2010/07/05.