3722-56-3

Basic information

• Product Name: (3S)-3,4-Dihydro-7-methoxy-3-(4-methoxyphenyl)-2H-1-benzopyran
• Synonyms: (3S)-3,4-Dihydro-7-methoxy-3-(4-methoxyphenyl)-2H-1-benzopyran;(S)-(-)-4',7-Dimethoxyisoflavan;(S)-4',7-Dimethyl Equol
• CAS NO: 3722-56-3
• Molecular Formula: C₁₇H₁₈O₃
• Molecular Weight: 270.32
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Aromatics, Chiral Reagents, Heterocycles
• Mol File: 3722-56-3.mol

Chemical Properties

• Melting Point: 90-91°C
• Boiling Point: 395.52°C at 760 mmHg
• Flash Point: 134.2°C
• Appearance: /
• Density: 1.129g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: (3S)-3,4-Dihydro-7-methoxy-3-(4-methoxyphenyl)-2H-1-benzopyran(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-3,4-Dihydro-7-methoxy-3-(4-methoxyphenyl)-2H-1-benzopyran(3722-56-3)
• EPA Substance Registry System: (3S)-3,4-Dihydro-7-methoxy-3-(4-methoxyphenyl)-2H-1-benzopyran(3722-56-3)

Safety Data

• Hazardous Substances Data: 3722-56-3(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 3722-56-3 differently. You can refer to the following data:
1. Intermediate for the synthesis of (S)-Equol
2. Intermediate for the synthesis of (S)-Equol.

InChI:InChI=1/C17H18O3/c1-18-15-6-3-12(4-7-15)14-9-13-5-8-16(19-2)10-17(13)20-11-14/h3-8,10,14H,9,11H2,1-2H3/t14-/m1/s1

Upstream product

• 77-78-1 dimethyl sulfate 
• 531-95-3 equol 
• 225090-14-2 (S)-2-(3-hydroxy-2-(4-methoxyphenyl)propyl)-5-methoxyphenol 
• 917379-11-4 (S)-3-(2-bromo-4-methoxyphenyl)-2-(4-methoxyphenyl)propan-1-ol 
• 917379-10-3 (S)-4-benzyl-3-((S)-3-(2-bromo-4-methoxyphenyl)-2-(4-methoxyphenyl)propanoyl)-2-oxazolidinone 
• 104-01-8 4-Methoxyphenylacetic acid 
• 143589-97-3 (4S)-3-<2-(4-Methoxyphenyl)-1-oxoethyl>-4-(phenylmethyl)-2-oxazolidinone 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 152955-15-2 4-methoxy-2-O-methoxymethylbenzyl bromide 
• 169125-12-6 (+)-(4S,5R)-1,5-dimethyl-4-phenyl-3-(4-methoxyphenylacetyl)-2-imidazolidinone 
• 225089-91-8 (S)-2-(4-methoxyphenyl)-3-(4-methoxy-2-O-methoxymethylphenyl)-1-propanol 
• 225089-86-1 (+)-(4S,5R)-1,5-dimethyl-4-phenyl-3-<2'-(4-methoxyphenyl)-3'-(4-methoxy-2-O-methoxymethylphenyl)>propionyl-2-imidazolidinone 
• 1404301-54-7 7-methoxy-3-(4-methoxyphenyl)hydrocoumarin 
• 1404301-87-6 (S)-7-methoxy-3-(4-methoxyphenyl)spiro[chroman-2,2'-[1,3]dithiane] 

Downstream Products

• 531-95-3 equol 
• 15236-11-0 (S)-7-methoxy-3-(4-methoxy-phenyl)-chroman-4-one 

Relevant articles and documents

Rhodium-catalyzed asymmetric addition of arylboronic acids to 2: H-chromenes leading to 3-arylchromane derivatives

Asymmetric addition of arylboronic acids to 2H-chromenes proceeded in the presence of a hydroxorhodium/chiral diene catalyst to give 3-arylchromanes in high yields with high enantioselectivity. The reaction involves 1,4-Rh shift before protonation to release the addition product and to regenerate the hydroxorhodium species.

A chiral pool approach for asymmetric syntheses of both antipodes of equol and sativan

For the first time, both antipodes of the isoflavans, equol and sativan were synthesized in >98% ee with good overall yields starting from readily available starting materials. The chiral isoflavan, (?)-equol is produced from soy isoflavones, formonentin and daidzein by the action of intestinal bacteria in certain groups of population and other chiral isoflavans are reported from various phytochemical sources. To produce these chiral isoflavans in gram quantities, Evans’ enantioselective aldol condensation was used as a chiral-inducing step to introduce the required chirality at the C-3 position. Addition of chiral boron-enolate to substituted benzaldehyde resulted in functionalized syn-aldol products with >90% yield and excellent diastereoselectivity. Functional group transformations followed by intramolecular Mitsunobu reaction and deprotection steps resulted the target compounds, S-(?)-equol and S-(+)-sativan, with high degree of enantiopurity. By simply switching the chiral auxiliary to (S)-4-benzyloxazolidin-2-one and following the same synthetic sequence the antipodes, R-(+)-equol and R-(?)-sativan were achieved. Both enantiomers are of interest from a clinical and pharmacological perspective and are currently being developed as nutraceutical and pharmacological agents. This flexible synthetic process lends itself quite readily to the enantioselective syntheses of other biologically active C-3 chiral isoflavans.

Iridium-Catalyzed Asymmetric Hydrogenation of 2H-Chromenes: A Highly Enantioselective Approach to Isoflavan Derivatives

A highly efficient (aS)-Ir/In-BiphPHOX-catalyzed asymmetric hydrogenation of substituted 2H-chromenes and substituted benzo[e][1,2]oxathiine 2,2-dioxides is described. A series of 2H-chromenes and benzo[e][1,2]oxathiine 2,2-dioxides were hydrogenated to give the target products in high yields (92-99%) with excellent enantioselectivities (up to 99.7% ee) using our catalytic system. This reaction provides a direct and efficient method for the construction of chiral benzo six-membered oxygen-containing compounds.

Deracemization of α-aryl hydrocoumarins via catalytic asymmetric protonation of ketene dithioacetals

An unprecedented catalytic asymmetric protonation of ketene dithioacetals is described. Various racemic α-aryl hydrocoumarin derivatives are transformed into enantioenriched dithioacetal-protected hydrocoumarins in the presence of a chiral Br?nsted acid catalyst. A newly developed phosphoric acid, featuring the 3,5-bis(pentafluorothio)phenyl (3,5-(SF5) 2C6H3) substituent, is introduced. The obtained products can be easily converted into either hydrocoumarins or the corresponding chromans via simple hydrolysis or hydrogenation, respectively.

Total synthesis of (S)-equol

The first enantioselective total synthesis of (S)-equol is reported. The described route relies on an Evans alkylation to form the stereocenter and an intramolecular Buchwald etherification to generate the chroman ring. Key features of this method include its brevity, its scalability, and the low cost of starting materials.

Stereoselective synthesis of isoflavonoids. (R)- and (S)-isoflavans

α-Benzylation of (+)- and (-)-N-phenylacetyl imidazolidinones with 2- O-methoxy-methylbenzyl bromides, followed by reductive removal of the chiral auxiliary and cyclization, afforded oxygenated isoflavans in excellent enantiomeric excess and yield.