1057663-19-0

Basic information

• Product Name: (S)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)propan-1-ol
• Synonyms: (S)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)propan-1-ol
• CAS NO: 1057663-19-0
• Molecular Weight: 302.37
• Mol File: 1057663-19-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)propan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)propan-1-ol(1057663-19-0)
• EPA Substance Registry System: (S)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)propan-1-ol(1057663-19-0)

Safety Data

• Hazardous Substances Data: 1057663-19-0(Hazardous Substances Data)

Upstream product

• 1057663-18-9 (4S)-5-(2,4-dimethoxyphenyl)-4-(4-methoxyphenyl)-pentane-2,3-diol 
• 848081-07-2 3-(2',4'-dimethoxyphenyl)propionaldehyde 
• 76104-56-8 3-(2,4-dimethoxyphenyl)propyl alcohol 
• 16909-09-4 (E)-3-(2,4-dimethoxyphenyl)-2-propenoic acid 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 73867-36-4 (E)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)acrylic acid 
• 1383121-29-6 (S)-3-(2,4-dimethoxyphenyl)-2-(4-methoxyphenyl)propionic acid 
• 104-01-8 4-Methoxyphenylacetic acid 

Downstream Products

• 1057663-20-3 (S)-1-(3-bromo-2-(4-methoxyphenyl)propyl)-2,4-dimethoxy-benzene 
• 531-95-3 equol 

Relevant articles and documents

A Concise Enantiodivergent Synthesis of Equol

Equol, a nonsteroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein, has been synthesized as both enantioenriched forms based on MacMillan's α-Arylation of carbonyl compound mediated by amino acid derived indazolidinones and copper precatalysts. The natural form of (S)-equol and its enantiomer (R)-equol have been synthesized in 8 steps from 2,4-dimethoxybenzaldehyde with good enantiomeric purity (90% ee and 90% ee, respectively).

Synthetic access to optically active isoflavans by using allylic substitution

A general approach to the (S)- and (R)-isoflavans was invented, and efficiency of the method was demonstrated by the synthesis of (S)-equol ((S)-3), (R)-sativan ((R)-4), and (R)-vestitol ((R)-5). The key step is the allylic substitution of (S)-6a (Ar1=2,4-(MeO)2C6H3) and (R)-6b (Ar1=2,4-(BnO)2C6H3) with copper reagents derived from CuBr·Me2S and Ar2-MgBr (7a, Ar2=4-MeOC6H4; 7b, 2,4-(MeO)2C6H3; 7c, 2-MOMO-4-MeOC6H3), furnishing anti SN2′ products (R)-8a and (S)-8b,c with 93-97% chirality transfer in 60-75% yields. The olefinic part of the products was oxidatively cleaved and the Me and Bn groups on the Ar1 moieties was then removed. Finally, phenol bromide 9a and phenol alcohols 9b,c underwent cyclization with K2CO3 and the Mitsunobu reagent to afford (S)-3 and (R)-4 and -5, respectively.