137790-18-2

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2-phenyl-5,7-bis(phenylmethoxy)-
• CAS NO: 137790-18-2
• Molecular Formula: C29H22O4
• Molecular Weight: 434.491
• Mol File: 137790-18-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2-phenyl-5,7-bis(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2-phenyl-5,7-bis(phenylmethoxy)-(137790-18-2)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2-phenyl-5,7-bis(phenylmethoxy)-(137790-18-2)

Safety Data

• Hazardous Substances Data: 137790-18-2(Hazardous Substances Data)

Upstream product

• 120979-97-7 (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 100-39-0 benzyl bromide 
• 591-50-4 iodobenzene 
• 903516-83-6 5,7-bis(benzyloxy)-4H-chromen-4-one 

Downstream Products

• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 4443-09-8 norwogonin 
• 110506-85-9 7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 906653-35-8 1-[2'-(3'',4''-diallyloxy[carbonyl-13C]benzyloxy)-4',6'-dibenzyloxyphenyl]-2-(2''',3''',4''',6'''-tetra-O-benzyl-β-D-glucopyranosyloxy)ethanone 
• 906653-33-6 1-(2',4'-dibenzyloxy-6'-hydroxyphenyl)-2-(2'',3'',4'',6''-tetra-O-benzyl-β-D-glucopyranosyloxy)ethanone 
• 137790-51-3 2-acetyl-3,5-bis(benzyloxy)phenyl benzoate 
• 906653-32-5 1-(2’,4’-dibenzyloxy-6’-hydroxyphenyl)-2-hydroxyethanone 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 

Relevant articles and documents

Total Synthesis of the Antiviral Natural Product Houttuynoid B

The first total synthesis of houttuynoid B, a powerful antiviral flavonoid glycoside from the Chinese plant Houttuynia cordata, is described. In a key step, a Baker-Venkataraman rearrangement employing an already glycosylated substrate was used to efficiently set up the fully functionalized carbon skeleton. The required benzofuran building block was prepared through a domino Sonogashira coupling/5-endo-dig cyclization and converted into a stable 1-hydroxybenzotriazole-derived active ester prior to linking with a galactosylated hydroxyacetophenone unit. The elaborated synthesis requires only nine steps (11 % overall yield) along the longest linear sequence and paves the way for the preparation of structurally related compounds for further biological evaluation.

Lewis acid-triggered selective zincation of chromones, quinolones, and thiochromones: Application to the preparation of natural flavones and isoflavones

A Lewis acid-triggered zincation allows the regioselective metalation of various chromones and quinolones. In the absence of MgCl2, a C(3) zincation is observed, whereas in the presence of MgCl2 or a related Lewis acid, C(2) zincation occurs. Applications to a natural flavone, isoflavone, and quinolone are shown.

Isotopic labelling of quercetin 3-glucoside

The potentially important dietary antioxidant, quercetin 3-O-β-d-glucoside, has been 13C-labelled at C-2 of the flavonoid unit by synthesis in 15% yield over five steps from [13C]carbon dioxide. The route is appropriate for radiochemical synthesis. Formation of the protected 3-glucosylated flavonol appears to result from [1,7]-sigmatropic rearrangement with migration of a benzyl group followed by cyclisation. A free 5-OH results even when a phosphazene superbase is used.