3-[(E)-(3-CHLOROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-ONE

Base Information

• Chemical Name: 3-[(E)-(3-CHLOROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-ONE
• CAS No.: 1262616-91-0
• Molecular Formula: C₁₆H₁₁ClO₂
• Molecular Weight: 270.715
• Mol file: 1262616-91-0.mol

Synonyms:(E)-3-(3-chlorobenzylidene)-4-chromanone

Chemical Property of 3-[(E)-(3-CHLOROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-ONE

Chemical Property:

Purity/Quality:

3-[(E)-(3-Chlorophenyl)methylidene]-2,3-dihydro-4H-chromen-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(E)-(3-CHLOROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-ONE

There total 1 articles about 3-[(E)-(3-CHLOROPHENYL)METHYLIDENE]-2,3-DIHYDRO-4H-CHROMEN-4-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: 65.0%

2,3-dihydro-4H-1-benzopyran-4-one (491-37-2) + m-Chlorobenzaldehyde (587-04-2) → (E)-3-(3-chlorobenzylidene)-4-chromanone (1262616-91-0)

Guidance literature:

With hydrogenchloride; In methanol; water; for 24h; Reflux;

DOI:10.1016/j.tet.2011.09.087

Reference yield: 96.0%

(E)-3-(3-chlorobenzylidene)-4-chromanone (1262616-91-0) + 2-formylthiophenol (29199-11-9) → (2'S,3S,4'R)-2'-(3-chlorophenyl)-4'-hydroxyspiro[chroman-3,3'-thiochroman]-4-one (1262616-64-7)

Guidance literature:

With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S,2R)-2-(piperidin-1-yl)-2,3-dihydro-1H-inden-1-yl)thiourea; In 5,5-dimethyl-1,3-cyclohexadiene; at -30 ℃; optical yield given as %ee; stereoselective reaction;

DOI:10.1039/c0cc03489d

Reference yield: 88.0%

(E)-3-(3-chlorobenzylidene)-4-chromanone (1262616-91-0) + methyl N-(4-chlorobenzylidene)glycinate (76862-09-4) → (2'R,3R,4'R,5'R)-methyl 4'-(3-chlorophenyl)-2'-(4-chlorophenyl)-4-oxospiro[chroman-3,3'-pyrrolidine]-5'-carboxylate (1333395-51-9)

Guidance literature:

With tetrakis(acetonitrile)copper(I)tetrafluoroborate; (S)-TF-Biphamphos; triethylamine; In dichloromethane; at -20 - 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1039/c1cc13554f

upstream raw materials:

2,3-dihydro-4H-1-benzopyran-4-one

m-Chlorobenzaldehyde

Downstream raw materials:

(2'S,3S,4'R)-2'-(3-chlorophenyl)-4'-hydroxyspiro[chroman-3,3'-thiochroman]-4-one

(S)-2-amino-4-(3-chlorophenyl)-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile

(2'R,3R,4'R,5'R)-methyl 4'-(3-chlorophenyl)-2'-(4-chlorophenyl)-4-oxospiro[chroman-3,3'-pyrrolidine]-5'-carboxylate

C₃₂H₂₂Cl₂O₄

Refernces