(S)-(+)-ethyl 4-oxocyclopent-2-ene acetate

Base Information

• Chemical Name: (S)-(+)-ethyl 4-oxocyclopent-2-ene acetate
• CAS No.: 107932-04-7
• Molecular Formula: C₉H₁₂O₃
• Molecular Weight: 168.192
• Mol file: 107932-04-7.mol

Synonyms:(S)-(+)-ethyl 4-oxocyclopent-2-ene acetate

Chemical Property of (S)-(+)-ethyl 4-oxocyclopent-2-ene acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(+)-ethyl 4-oxocyclopent-2-ene acetate

There total 1 articles about (S)-(+)-ethyl 4-oxocyclopent-2-ene acetate 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:

(R)-4-acetoxycyclopent-2-en-1-one (59995-48-1) → (S)-(+)-ethyl 4-oxocyclopent-2-ene acetate (107932-04-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / K₂CO₃, 18-crown-6 / toluene / 48 h / 0 °C

2: Pd(OAc)2, PPh₃, Et₃N, formic acid / dioxane / 3 h / Heating

3: 45 percent / formic acid / 2 h / Ambient temperature

4: 91 percent / NaHCO₃ / dimethylformamide / 6 h / Ambient temperature

With palladium diacetate; formic acid; 18-crown-6 ether; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; In 1,4-dioxane; formic acid; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(97)00614-5

Reference yield:

(S)-(+)-ethyl 4-oxocyclopent-2-ene acetate (107932-04-7) → coronatine benzyl ester (189506-61-4)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd-C / ethanol / 24 h / Ambient temperature

2: 85 percent / PPTS / benzene / 24 h / Heating

4: 94 percent / aq. p-TsOH / acetone / 24 h / Ambient temperature

5: NaH / ethanol / 0 deg C to rt

6: 70 percent / aq. HCl / Heating

7: 89 percent / Et₃N, DMAP, EtN=C=N(CH₂)3NMe₂*HCl / CH₂Cl₂ / 24 h / Ambient temperature

With hydrogenchloride; dmap; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; acetone; benzene;

DOI:10.1016/S0040-4020(97)00614-5

Reference yield:

(S)-(+)-ethyl 4-oxocyclopent-2-ene acetate (107932-04-7) → (+)-coronatine (62251-96-1)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / Pd-C / ethanol / 24 h / Ambient temperature

2: 85 percent / PPTS / benzene / 24 h / Heating

4: 94 percent / aq. p-TsOH / acetone / 24 h / Ambient temperature

5: NaH / ethanol / 0 deg C to rt

6: 70 percent / aq. HCl / Heating

7: 89 percent / Et₃N, DMAP, EtN=C=N(CH₂)3NMe₂*HCl / CH₂Cl₂ / 24 h / Ambient temperature

8: 80 percent / H₂ / Pd-C / ethyl acetate / 0.33 h / Ambient temperature

With hydrogenchloride; dmap; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate; acetone; benzene;

DOI:10.1016/S0040-4020(97)00614-5

upstream raw materials:

(R)-4-acetoxycyclopent-2-en-1-one

Downstream raw materials:

(+)-coronafacic acid

(+)-coronatine

coronatine benzyl ester

Refernces

• 1、 Toshima, Hiroaki,Nara, Shinji,Ichihara, Akitami. "Asymmetric total syntheses of (+)-coronafacic acid and (+)-coronatine". . p. 752 - 753. Retrieved 2007/10/03.