349547-18-8

Basic information

• Product Name: (4S)-6-Methyl-4-phenylchroman-2-one
• Synonyms: (4S)-6-Methyl-4-phenylchroman-2-one;(4S)-3,4-Dihydro-6-methyl-4-phenyl-2H-1-benzopyran-2-one
• CAS NO: 349547-18-8
• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 238.28
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 349547-18-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 351.1 °C at 760 mmHg
• Flash Point: 146.3 °C
• Appearance: /
• Density: 1.166 g/cm³
• Vapor Pressure: 4.2E-05mmHg at 25°C
• Refractive Index: 1.595
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: (4S)-6-Methyl-4-phenylchroman-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-6-Methyl-4-phenylchroman-2-one(349547-18-8)
• EPA Substance Registry System: (4S)-6-Methyl-4-phenylchroman-2-one(349547-18-8)

Safety Data

• Hazardous Substances Data: 349547-18-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Intermediate in the production of Tolterodine.

InChI:InChI=1/C16H14O2/c1-11-7-8-15-14(9-11)13(10-16(17)18-15)12-5-3-2-4-6-12/h2-9,13H,10H2,1H3/t13-/m0/s1

Upstream product

• 16299-22-2 6-methyl-4-phenylchromen-2-one 
• 92-48-8 6-methylcoumarin 
• 98-80-6 phenylboronic acid 
• 86608-97-1 2-(1-hydroxy-1-phenylethyl)-4-methylphenol 
• 100-58-3 phenylmagnesium bromide 
• 201230-82-2 carbon monoxide 
• 102-92-1 Cinnamoyl chloride 
• 1240326-57-1 (R)-4-isopropyl-3-[(E)-(3-phenylacryloyl)]oxazolidin-2-one 
• 112459-60-6 (4S)-4-isopropyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 
• 637330-73-5 (4S,2'E)-3-(3'-phenylacryloyl)-4-phenyl-5,5-dimethyloxazolidin-2-one 
• 141209-95-2 (4S)-4-phenyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 851789-43-0 3-phenyl-3-(2'-hydroxy-5'-methyl)phenylpropanol-1 
• 124937-53-7 (S)-tolterodine 

Relevant articles and documents

BICMAP-rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins

Rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids 2 to coumarins 1 using (S)-BICMAP as a chiral ligand gave the desired 4-arylchroman-2-one derivatives 2 in good yields and with high enantioselectivities (up to 99% ee).

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.

Catalytic Asymmetric Addition of Meldrum's Acid, Malononitrile, and 1,3-Dicarbonyls to ortho-Quinone Methides Generated In Situ under Basic Conditions

A new approach to the utilization of highly reactive and unstable ortho-quinone methides (o-QMs) in catalytic asymmetric settings is presented. The enantioselective reactions are catalysed by bifunctional organocatalysts, and the o-QM intermediates are formed in situ from 2-sulfonylalkyl phenols through base-promoted elimination of sulfinic acid. The use of mild Bronsted basic conditions for transiently generating o-QMs in catalytic asymmetric processes is unprecedented, and allows engaging productively in the reactions nucleophiles such as Meldrum's acid, malononitrile and 1,3-dicarbonyls. The catalytic transformations give new and general entries to 3,4-dihydrocoumarins, 4H-chromenes and xanthenones. These frameworks are recurring structures in natural product and medicinal chemistry, as testified by the formal syntheses of (R)-tolterodine and (S)-4-methoxydalbergione from the catalytic adducts.