6-Heptenoic acid, 2-[(4E)-5-(4-methylphenyl)-4-pentenyl]-7-phenyl-, (6E)-

Base Information

• Chemical Name: 6-Heptenoic acid, 2-[(4E)-5-(4-methylphenyl)-4-pentenyl]-7-phenyl-, (6E)-
• CAS No.: 824431-52-9
• Molecular Formula: C25H30O2
• Molecular Weight: 362.512
• Mol file: 824431-52-9.mol

Synonyms:

Chemical Property of 6-Heptenoic acid, 2-[(4E)-5-(4-methylphenyl)-4-pentenyl]-7-phenyl-, (6E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-Heptenoic acid, 2-[(4E)-5-(4-methylphenyl)-4-pentenyl]-7-phenyl-, (6E)-

There total 10 articles about 6-Heptenoic acid, 2-[(4E)-5-(4-methylphenyl)-4-pentenyl]-7-phenyl-, (6E)- 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:

4-tolyl iodide (624-31-7) → (6E)-2-[(4E)-5-phenylpent-4-enyl]-7-(p-tolyl)hept-6-enoic acid (824431-52-9)

Guidance literature:

Multi-step reaction with 5 steps

1: PPh₃; NaOH / palladium(II) acetate / tetrahydrofuran / Heating

2: 2.06 g / hydrochloric acid / tetrahydrofuran / 4 h / 20 °C

3: 82 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 0 - 20 °C

4: 80 percent / cesium carbonate / acetonitrile / 72 h / 20 °C

5: 70 percent / H₂O / tetrahydrofuran / 4 h / 165 °C / microwave irradiation

With 1H-imidazole; hydrogenchloride; sodium hydroxide; water; iodine; caesium carbonate; triphenylphosphine; palladium diacetate; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Suzuki coupling;

DOI:10.1021/jo0483466

Reference yield:

(E)-3-phenylpropenal (14371-10-9) → (6E)-2-[(4E)-5-phenylpent-4-enyl]-7-(p-tolyl)hept-6-enoic acid (824431-52-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / BH₃*HNMe₂ / methanol / 3 h / 20 °C

2: 90 percent / 1.5 h / 170 °C / microwave irradiation

3: 100 percent / DIBALH / tetrahydrofuran; CH₂Cl₂ / 4 h / -78 °C

4: 87 percent / DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 5.25 h / -78 - 20 °C

5: 49 percent / BH₃*HNMe₂ / methanol / 3 h / 20 °C

6: 80 percent / cesium carbonate / acetonitrile / 72 h / 20 °C

7: 70 percent / H₂O / tetrahydrofuran / 4 h / 165 °C / microwave irradiation

With oxalyl dichloride; dimethylamine borane; water; diisobutylaluminium hydride; caesium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 1: Knoevenagel condensation / 4: Swern oxidation / 5: Knoevenagel condensation;

DOI:10.1021/jo0483466

Reference yield:

(E)-2,2-dimethyl-5-(3-phenylallyl)-1,3-dioxane-4,6-dione (72651-96-8,121740-84-9) → (6E)-2-[(4E)-5-phenylpent-4-enyl]-7-(p-tolyl)hept-6-enoic acid (824431-52-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / 1.5 h / 170 °C / microwave irradiation

2: 100 percent / DIBALH / tetrahydrofuran; CH₂Cl₂ / 4 h / -78 °C

3: 87 percent / DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 5.25 h / -78 - 20 °C

4: 49 percent / BH₃*HNMe₂ / methanol / 3 h / 20 °C

5: 80 percent / cesium carbonate / acetonitrile / 72 h / 20 °C

6: 70 percent / H₂O / tetrahydrofuran / 4 h / 165 °C / microwave irradiation

With oxalyl dichloride; dimethylamine borane; water; diisobutylaluminium hydride; caesium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 3: Swern oxidation / 4: Knoevenagel condensation;

DOI:10.1021/jo0483466

upstream raw materials:

(E)-3-phenylpropenal

(E)-2,2-dimethyl-5-(3-phenylallyl)-1,3-dioxane-4,6-dione

(E)-ethyl 5-phenylpent-4-enoate

4-tolyl iodide

Downstream raw materials:

(E)-2-((E)-5-Phenyl-pent-4-enyl)-7-p-tolyl-hept-6-enoyl chloride