ethyl 1-((E)-2-(methoxycarbonyl)-3-phenylallyl)-2-oxocyclopentane-1-carboxylate

Base Information

• Chemical Name: ethyl 1-((E)-2-(methoxycarbonyl)-3-phenylallyl)-2-oxocyclopentane-1-carboxylate
• CAS No.: 1617568-05-4
• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.381
• Mol file: 1617568-05-4.mol

Synonyms:ethyl 1-((E)-2-(methoxycarbonyl)-3-phenylallyl)-2-oxocyclopentane-1-carboxylate

Chemical Property of ethyl 1-((E)-2-(methoxycarbonyl)-3-phenylallyl)-2-oxocyclopentane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 1-((E)-2-(methoxycarbonyl)-3-phenylallyl)-2-oxocyclopentane-1-carboxylate

There total 4 articles about ethyl 1-((E)-2-(methoxycarbonyl)-3-phenylallyl)-2-oxocyclopentane-1-carboxylate 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: 95.0%

methyl 3-hydroxy-2-methylidene-3-phenylpropionate (18020-59-2) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → ethyl 1-((E)-2-(methoxycarbonyl)-3-phenylallyl)-2-oxocyclopentane-1-carboxylate (1617568-05-4)

Guidance literature:

With calcium(II) bis(trifluoromethanesulfonyl)imide; triethylamine; In acetonitrile; at 30 ℃; for 48h; Reagent/catalyst; Solvent; Catalytic behavior; Schlenk technique; Green chemistry;

DOI:10.1021/acs.orglett.9b03730

Reference yield:

(S)-methyl 2-(((tert-butoxycarbonyl)oxy)(phenyl)methyl)acrylate + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → ethyl 1-((E)-2-(methoxycarbonyl)-3-phenylallyl)-2-oxocyclopentane-1-carboxylate (1617568-05-4) + ethyl (R)-1-((R)-2-(methoxycarbonyl)-1-phenylallyl)-2-oxocyclopentane-1-carboxylate (1617568-04-3) + ethyl (S)-1-((S)-2-(methoxycarbonyl)-1-phenylallyl)-2-oxocyclopentane-1-carboxylate + ethyl 1-(2-(methoxycarbonyl)-1-phenylallyl)-2-oxocyclopentanecarboxylate

Guidance literature:

With C₁₉H₂₄N₂O₂; In tert-butyl methyl ether; at 20 ℃; for 16h; Solvent; stereoselective reaction;

DOI:10.1039/c4ob00682h

Reference yield:

methyl (S)-3-hydroxy-3-phenyl-2-methylenepropanoate (18020-59-2,98837-37-7,140630-33-7,108945-27-3) → ethyl 1-((E)-2-(methoxycarbonyl)-3-phenylallyl)-2-oxocyclopentane-1-carboxylate (1617568-05-4) + ethyl (R)-1-((R)-2-(methoxycarbonyl)-1-phenylallyl)-2-oxocyclopentane-1-carboxylate (1617568-04-3) + ethyl (S)-1-((S)-2-(methoxycarbonyl)-1-phenylallyl)-2-oxocyclopentane-1-carboxylate + ethyl 1-(2-(methoxycarbonyl)-1-phenylallyl)-2-oxocyclopentanecarboxylate

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / dichloromethane / 20 °C

2: C₁₉H₂₄N₂O₂ / tert-butyl methyl ether / 16 h / 20 °C

With dmap; C₁₉H₂₄N₂O₂; In dichloromethane; tert-butyl methyl ether;

DOI:10.1039/c4ob00682h

upstream raw materials:

methyl (S)-3-hydroxy-3-phenyl-2-methylenepropanoate

benzaldehyde

2-ethoxycarbonyl-1-cyclopentanone

methyl 3-hydroxy-2-methylidene-3-phenylpropionate