N₁-(2-hydroxy-5-oxocyclopent-1-enyl)-7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C₂]hepta-2,4,6-trienamide

Base Information

• Chemical Name: N₁-(2-hydroxy-5-oxocyclopent-1-enyl)-7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C₂]hepta-2,4,6-trienamide
• CAS No.: 1025811-52-2
• Molecular Formula: C₁₉H₁₈N₂O₆
• Molecular Weight: 372.34

Synonyms:N₁-(2-hydroxy-5-oxocyclopent-1-enyl)-7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C₂]hepta-2,4,6-trienamide

Chemical Property of N₁-(2-hydroxy-5-oxocyclopent-1-enyl)-7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C₂]hepta-2,4,6-trienamide

Chemical Property:

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Technology Process of N₁-(2-hydroxy-5-oxocyclopent-1-enyl)-7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C₂]hepta-2,4,6-trienamide

There total 6 articles about N₁-(2-hydroxy-5-oxocyclopent-1-enyl)-7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C₂]hepta-2,4,6-trienamide 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:

2-amino-3-hydroxy-2-cyclopenten-1-one hydrochloride (82659-07-2) + C12(13)C2H12ClNO4 → N1-(2-hydroxy-5-oxocyclopent-1-enyl)-7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C2]hepta-2,4,6-trienamide (1025811-52-2)

Guidance literature:

With pyridine; dmap; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/ja039336+

Reference yield:

5-(4-methoxy-3-nitrophenyl)-(2E,4E)-penta-2,4-dienal (685523-47-1) → N1-(2-hydroxy-5-oxocyclopent-1-enyl)-7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C2]hepta-2,4,6-trienamide (1025811-52-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 67.3 percent / aq. K₂CO₃ / 72 h / 20 °C

2: 93 percent / aq. LiOH / tetrahydrofuran / 48 h / 20 °C

3: oxalyl chloride; DMF / CH₂Cl₂ / 2 h / 20 °C

4: 577 mg / pyridine; DMAP / CH₂Cl₂; dimethylformamide / 2 h / 20 °C

With pyridine; dmap; lithium hydroxide; oxalyl dichloride; potassium carbonate; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Wadsworth-Emmons reaction;

DOI:10.1021/ja039336+

Reference yield:

(2E,4E)-5-(4-Methoxy-3-nitro-phenyl)-penta-2,4-dien-1-ol → N1-(2-hydroxy-5-oxocyclopent-1-enyl)-7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C2]hepta-2,4,6-trienamide (1025811-52-2)

Guidance literature:

Multi-step reaction with 5 steps

1: MnO₂

2: 67.3 percent / aq. K₂CO₃ / 72 h / 20 °C

3: 93 percent / aq. LiOH / tetrahydrofuran / 48 h / 20 °C

4: oxalyl chloride; DMF / CH₂Cl₂ / 2 h / 20 °C

5: 577 mg / pyridine; DMAP / CH₂Cl₂; dimethylformamide / 2 h / 20 °C

With pyridine; dmap; manganese(IV) oxide; lithium hydroxide; oxalyl dichloride; potassium carbonate; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: Wadsworth-Emmons reaction;

DOI:10.1021/ja039336+

upstream raw materials:

2-amino-3-hydroxy-2-cyclopenten-1-one hydrochloride

5-(4-methoxy-3-nitrophenyl)-(2E,4E)-penta-2,4-dienal

ethyl 7-(4-methoxy-3-nitrophenyl)-(2E,4E,6E)-[1,2-13C₂]hepta-2,4,6-trienoate

Downstream raw materials:

N₁-(2-hydroxy-5-oxocyclopent-1-enyl)-7-(3-amino-4-methoxyphenyl)-(2E,4E,6E)-[1,2-13C₂]hepta-2,4,6-trienamide

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