13738-92-6

Basic information

• Product Name: 2,2'-Bis(4-methoxyphenyl)-5,5'-dihydroxy-7,7'-dimethoxy-8,8'-bi(4H-1-benzopyran)-4,4'-dione
• Synonyms: 2,2'-Bis(4-methoxyphenyl)-5,5'-dihydroxy-7,7'-dimethoxy-8,8'-bi(4H-1-benzopyran)-4,4'-dione;5,5''-Dihydroxy-4',4''',7,7''-tetramethoxy-8,8''-biflavone;5,5'-Dihydroxy-7,7'-dimethoxy-2,2'-bis(4-methoxyphenyl)[8,8'-bi(4H-1-benzopyran)]-4,4'-dione;5,5'-Dihydroxy-7,7'-dimethoxy-2,2'-bis(4-methoxyphenyl)-8,8'-bi(4H-1-benzopyran)-4,4'-dione;Cupressufelvone7,4',7'',4'''-tetramethyl ether;WB-1
• CAS NO: 13738-92-6
• Molecular Formula: C₃₄H₂₆O₁₀
• Molecular Weight: 594.56424
• Mol File: 13738-92-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2'-Bis(4-methoxyphenyl)-5,5'-dihydroxy-7,7'-dimethoxy-8,8'-bi(4H-1-benzopyran)-4,4'-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Bis(4-methoxyphenyl)-5,5'-dihydroxy-7,7'-dimethoxy-8,8'-bi(4H-1-benzopyran)-4,4'-dione(13738-92-6)
• EPA Substance Registry System: 2,2'-Bis(4-methoxyphenyl)-5,5'-dihydroxy-7,7'-dimethoxy-8,8'-bi(4H-1-benzopyran)-4,4'-dione(13738-92-6)

Safety Data

• Hazardous Substances Data: 13738-92-6(Hazardous Substances Data)

Upstream product

• 187404-36-0 C₃₄H₃₆I₂O₈ 
• 187404-34-8 [(1R,2S)-3-Benzyloxy-1-benzyloxymethyl-2-(2-iodo-3,5-dimethoxy-phenoxy)-propoxy]-tert-butyl-dimethyl-silane 
• 187404-35-9 (2R,3S)-1,4-Bis-benzyloxy-3-(2-iodo-3,5-dimethoxy-phenoxy)-butan-2-ol 
• 187404-37-1 2-iodo-3,5-dimethyoxyphenol 
• 123-11-5 4-methoxy-benzaldehyde 
• 35134-71-5 (aS)-(+)-2,2'-dihydroxy-3,3'-diacetyl-4,4',6,6'-tetramethoxybiphenyl 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 13738-92-6 cupressuflavone 4',4',7,7-tetramethyl ether 
• 21286-54-4 Camphorsulfonyl chloride 
• 1734-84-5 (E)-1-(2-hydroxy-3-iodo-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 3420-72-2 2'-hydroxy-4,4',6'-trimethoxychalcone 

Downstream Products

• 13738-92-6 (-)-5,5''-dihydroxy-4',4''',7,7''-tetramethoxy-8,8''-biflavone 
• 2222-38-0 (-)-4',4''',5,5'',7,7''-hexamethoxy-8,8''-biflavone 

Relevant articles and documents

Total Synthesis and Absolute Stereochemistry of the Natural Atropisomer of the Biflavone 4′4?,7″-Tetra-O-methylcupressuflavone

The total synthesis of a natural atropisomer, 4′,4?,7,7″-tetra-O-methylcupressuflavone (1), has been achieved. The key intermediate, 3,3′-diacetyl-4,4′,6,6′-tetramethoxy-2,2′-biphenyldiol (5), was synthesized by the solid state phenol coupling reaction, and the racemate 5 was enantioresolved as bis(camphanate) esters. The absolute configuration of bis(camphanate) ester (-)-8b was determined to be (aR) by X-ray analysis. The ester (aR)-(-)-8b was converted to the natural biflavone [CD(+)362.0]-(-)-1, leading to the (aR) absolute configuration of 1. This conclusion is consistent with our previous theoretical determination of the absolute stereochemistry of biflavone 1 by the molecular orbital calculation of CD spectra.

Synthesis, resolution, and absolute configuration of optically pure 5,5''-dihydroxy-4',4''',7,7''-tetramethoxy-8,8''-biflavone and its derivatives

Optically pure 5,5-dihydroxy-4,4''',7,7''-tetramethoxy-8,8''-biflavone (1) and its dimethyl derivative 5 were synthesized for the first time. Resolution of the racemic (±)-1, prepared by a modified literature procedure, was performed via the formation and recrystallization of its (+)- and (-)-camphorsulfonate 6. Hydrolysis of the (+)- or (-)-camphorsulfonate 6 afforded optically pure (+) or (-)-1, which was then methylated to give (+)- or (-)-5. The absolute configurations of (+)-1 and (-)-1, assigned as (aR) and (aS), respectively, were confirmed in an unambiguous manner by X-ray single crystal analysis and from their CD spectra.