(4r)-6-Methyl-4-phenylchroman-2-one

Base Information

• Chemical Name: (4r)-6-Methyl-4-phenylchroman-2-one
• CAS No.: 827007-19-2
• Molecular Formula: C16H14O2
• Molecular Weight: 238.286
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID80359003
• Nikkaji Number: J1.265.474J
• Wikidata: Q72494743
• Mol file: 827007-19-2.mol

Synonyms:(4r)-6-methyl-4-phenylchroman-2-one;827007-19-2;(4R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one;SCHEMBL5269737;DTXSID80359003;SUHIZPDCJOQZLN-CYBMUJFWSA-N;AMY13904;6-methyl-4-(r)-phenyl-dihydrocumarin;(4R)-6-Methyl-4-phenyl-3,4-dihydro-2H-1-benzopyran-2-one

Chemical Property of (4r)-6-Methyl-4-phenylchroman-2-one

Chemical Property:

• Vapor Pressure: 4.2E-05mmHg at 25°C
• Refractive Index: 1.595
• Boiling Point: 351.1 °C at 760 mmHg
• Flash Point: 146.3 °C
• PSA: 26.30000
• Density: 1.166g/cm³
• LogP: 3.43600
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 238.099379685
• Heavy Atom Count: 18
• Complexity: 306

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)OC(=O)CC2C3=CC=CC=C3
• Isomeric SMILES: CC1=CC2=C(C=C1)OC(=O)C[C@@H]2C3=CC=CC=C3

Technology Process of (4r)-6-Methyl-4-phenylchroman-2-one

There total 38 articles about (4r)-6-Methyl-4-phenylchroman-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(R)-3-[(R)-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionyl]-4-phenyl-5,5-dimethyloxazolidin-2-one → (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one (827007-19-2)

Guidance literature:

(R)-3-[(R)-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionyl]-4-phenyl-5,5-dimethyloxazolidin-2-one; With boron tribromide; In dichloromethane; at -75 - -3 ℃;

With triethylamine; In toluene; for 1h; Reflux;

DOI:10.1016/j.tetasy.2016.07.003

Reference yield: 96.0%

(S)-3-[(S)-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionyl]-4-isobutyl-5,5-dimethyloxazolidin-2-one → (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one (827007-19-2) + (S)-6-methyl-4-phenylchroman-2-one (349547-18-8)

Guidance literature:

(S)-3-[(S)-3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionyl]-4-isobutyl-5,5-dimethyloxazolidin-2-one; With boron tribromide; In dichloromethane; at -75 - -3 ℃;

With triethylamine; In toluene; for 1h; Reflux;

DOI:10.1016/j.tetasy.2016.07.003

Reference yield: 95.0%

6-methylcoumarin (92-48-8) + phenylboronic acid (98-80-6) → (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one (827007-19-2)

Guidance literature:

With chlorobis(ethylene)rhodium(I) dimer; (R,R)-1,4-dimethyl-2,5-di(4'-methoxylphenyl)bicyclo[2.2.2]octane-2,5-diene; potassium hydroxide; In 1,4-dioxane; water; at 30 ℃; for 3h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.200907033

upstream raw materials:

5-methyl-3-phenyl-2,3-dihydro-1H-inden-1-one

6-methylcoumarin

phenylboronic acid

6-methyl-4-phenylchromen-2-one

Downstream raw materials:

3-phenyl-3-(2'-hydroxy-5'-methyl)phenylpropanol-1

(R)-(+)-tolterodine

tolterodine tartrate

(R)-3-[2-(benzyloxy)-5-methylphenyl]-3-phenylpropyl 4-nitrobenzenesulfonate