77015-47-5

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 3-[(4-chlorophenyl)methylene]-2,3-dihydro-2-phenyl-, (3E)-
• CAS NO: 77015-47-5
• Molecular Formula: C22H15ClO2
• Molecular Weight: 346.813
• Mol File: 77015-47-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 3-[(4-chlorophenyl)methylene]-2,3-dihydro-2-phenyl-, (3E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 3-[(4-chlorophenyl)methylene]-2,3-dihydro-2-phenyl-, (3E)-(77015-47-5)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 3-[(4-chlorophenyl)methylene]-2,3-dihydro-2-phenyl-, (3E)-(77015-47-5)

Safety Data

• Hazardous Substances Data: 77015-47-5(Hazardous Substances Data)

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 487-26-3 Flavanone 
• 112014-59-2 (Z)-2,3-Dihydro-3-<(4-chlorophenyl)methylene>-2-phenyl-4H-1-benzopyran-4-one 

Downstream Products

• 119139-32-1 4''-chloro-3-α-hydroxybenzylflavone 
• 65485-14-5 3-[(4-chlorophenyl)carbonyl]-2-phenyl-4H-chromen-4-one 
• 112014-59-2 (Z)-2,3-Dihydro-3-<(4-chlorophenyl)methylene>-2-phenyl-4H-1-benzopyran-4-one 

Relevant articles and documents

Structure-cytotoxic activity relationship of 3-arylideneflavanone and chromanone (E,Z isomers) and 3-arylflavones

The E,Z-isomers of 3-arylidene substituted flavanone, chromanone and 3-aryl substituted flavone derivatives were tested in vitro for their cytotoxic activity against three cancer cell lines (HL-60, NALM-6, WM-115) and normal cell line (HUVEC). It was observed that substitution at C3 position led to significant enhance in cytotoxicity. Isomeric configuration of 3-arylideneflavanones had an influence on the cytotoxic potential. Multiple regression analysis combined with variable selection by genetic algorithm was used to model relationships between molecular descriptors and the cytotoxic activity. The most accurate QSAR models were based on a combination between energy of LUMO, experimental value of log P and partial charge on carbonyl oxygen (δO2).

NMR spectral studies of several series of E-3-arylideneflavanones: Realisation of some steric and electronic interactions

H-2 of E-3-arylideneflavanones differing only in the β-phenyl group is found to experience a reverse substituent chemical shift (s.c.s.) effect.An unfavourable steric interaction between this proton and the ortho-protons of β-phenyl group has been related to this observation.An interesting feature in the 1H NMR spectra of the heterocyclic analogs 5a-c is the significant deshielding of H-2 and shielding of H-β in the case of 5a.Intramolecular hydrogen bond formation between H-2 and the furano oxygen of 5a is probably responsible for this observation.From a studyof the 1H and 13C NMR spectral features of 8a-e which differ only in the 4'-substituent, it may be concluded that a 4'-substituent can polarise the C3-C-β and C=O ?-bonds as well as the ?-system of ring-A.The results of dual substituent parameter analysis of s.c.s. values of C-3, C-β, C-4, C-8a and C-6 for the series 8 have also been presented.

A simple convenient synthesis of 3-Benzylideneflavanones.

-