828933-86-4

Basic information

• Product Name: 2H-1-Benzopyran-2-ol, 3,4-dihydro-6-methyl-4-phenyl-, (4R)-
• CAS NO: 828933-86-4
• Molecular Formula: C16H16O2
• Molecular Weight: 240.302
• Mol File: 828933-86-4.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 2H-1-Benzopyran-2-ol, 3,4-dihydro-6-methyl-4-phenyl-, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-2-ol, 3,4-dihydro-6-methyl-4-phenyl-, (4R)-(828933-86-4)
• EPA Substance Registry System: 2H-1-Benzopyran-2-ol, 3,4-dihydro-6-methyl-4-phenyl-, (4R)-(828933-86-4)

Safety Data

• Hazardous Substances Data: 828933-86-4(Hazardous Substances Data)

Upstream product

• 827007-19-2 (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one 
• 86608-97-1 2-(1-hydroxy-1-phenylethyl)-4-methylphenol 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 6627-55-0 2-bromo-p-cresol 
• 175647-90-2 (E)-ethyl 3-(2-hydroxy-5-methylphenyl)acrylate 
• 16299-22-2 6-methyl-4-phenylchromen-2-one 
• 1152781-52-6 (R)-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanenitrile 
• 828933-84-2 tert-butyl (2-formyl-4-methylphenyl) carbonate 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 98-80-6 phenylboronic acid 
• 92-48-8 6-methylcoumarin 
• 828933-85-3 (2S,4R)-6-Methyl-4-phenyl-2-((1R,2S)-2-phenyl-cyclohexyloxy)-chroman 

Downstream Products

• 827007-19-2 (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one 
• 124937-51-5 (R)-(+)-tolterodine 
• 124937-52-6 tolterodine tartrate 
• 851789-43-0 3-phenyl-3-(2'-hydroxy-5'-methyl)phenylpropanol-1 

Relevant articles and documents

Asymmetric Hydroesterification of Diarylmethyl Carbinols

An efficient asymmetric hydroesterfication of diarylmethyl carbinols is developed for the first time with a Pd-WingPhos catalyst, resulting in a series of chiral 4-aryl-3,4-dihydrocoumarins in excellent enantioselectivities and good yields. The method features mild reaction conditions, a broad substrate scope, use of easily accessible starting materials, and low palladium loadings. A plausible stereochemical model is also proposed with the Pd-WingPhos catalyst. This method has enabled a 4-step asymmetric synthesis of (R)-tolterodine from readily available starting materials.

Chiral Inductive Diastereoconvergent Allylation Reactions of Allyltrimethylsilane and Diastereomixtures of Diarylmethanols Catalyzed by FeCl3

We report the chiral-auxiliary-controlled diastereoconvergent allylation reactions of allyltrimethylsilane with diastereomeric mixtures of diarylmethanols in the presence of FeCl3 as a Lewis acid catalyst. This reaction was successfully applied to a variety of substrates; it proceeded irrespective of the substituent on the aromatic ring of the substrate. The present method was used as the key step in synthesizing (R)-tolterodine.

Coumarins from free ortho -hydroxy cinnamates by Heck-Matsuda arylations: A scalable total synthesis of (R)-tolterodine

Free ortho-hydroxy cinnamate ester derivatives are evaluated in the synthesis of structurally diverse 4-aryl-coumarins via a tandem Heck-Matsuda cyclization reaction. Free phenolic groups were considered incompatible with such a reaction, which usually provide the corresponding diazo dyes. A concise and scalable route employing a ligand-free, Pd-catalyzed Heck-Matsuda arylation under aerobic conditions for the preparation of (R)-Tolterodine in high overall yield and ee is also presented.