2-(2-Phenylethenyl)-2,3-dihydro-4H-pyran-4-one

Base Information

• Chemical Name: 2-(2-Phenylethenyl)-2,3-dihydro-4H-pyran-4-one
• CAS No.: 85613-04-3
• Molecular Formula: C13H12O2
• Molecular Weight: 200.237
• DSSTox Substance ID: DTXSID00706954
• Mol file: 85613-04-3.mol

Synonyms:85613-04-3;2-(2-Phenylethenyl)-2,3-dihydro-4H-pyran-4-one;DTXSID00706954

Chemical Property of 2-(2-Phenylethenyl)-2,3-dihydro-4H-pyran-4-one

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 200.083729621
• Heavy Atom Count: 15
• Complexity: 272

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC=CC1=O)C=CC2=CC=CC=C2

Technology Process of 2-(2-Phenylethenyl)-2,3-dihydro-4H-pyran-4-one

There total 10 articles about 2-(2-Phenylethenyl)-2,3-dihydro-4H-pyran-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: 82.0%

(E)-3-phenylpropenal (14371-10-9) + danishefsky's diene (54125-02-9) → 2-(E-styryl)-2,3-dihydro-4H-pyran-4-one (85613-04-3)

Guidance literature:

(E)-3-phenylpropenal; danishefsky's diene; With (R)-H₄-BINOL Ti(IV); at 20 ℃; for 96h;

With trifluoroacetic acid; at 20 ℃; Further stages.;

DOI:10.1002/1521-3765(20021104)8:21<5033::AID-CHEM5033>3.0.CO;2-T

Reference yield: 79.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 2-vinyl-2H-pyran-4(3H)-one (82093-20-7) → 2-(E-styryl)-2,3-dihydro-4H-pyran-4-one (85613-04-3)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(l) iodide; In dichloromethane; Inert atmosphere; Reflux;

DOI:10.1016/j.bmc.2012.03.059

Reference yield: 75.0%

(1E,6E)-1-Methoxy-7-phenyl-5-trimethylsilanyloxy-hepta-1,6-dien-3-one (91879-81-1) → (1E,6E)-5-hydroxy-1-methoxy-7-phenylhepta-1,6-dien-3-one (91879-80-0) + 2-(E-styryl)-2,3-dihydro-4H-pyran-4-one (85613-04-3)

Guidance literature:

boron trifluoride diethyl etherate; In diethyl ether; at -78 ℃; for 4h;

DOI:10.1021/ja00291a026

upstream raw materials:

(E)-3-phenylpropenal

danishefsky's diene

(1E,6E)-5-hydroxy-1-methoxy-7-phenylhepta-1,6-dien-3-one

(1E,6E)-1-Methoxy-7-phenyl-5-trimethylsilanyloxy-hepta-1,6-dien-3-one

Downstream raw materials:

(E)-4-Methoxy-1-[6-((E)-styryl)-4-trimethylsilanyloxy-5,6-dihydro-2H-pyran-2-yl]-but-3-en-2-one

(E)-2-styryl-4H-pyran-4-one