21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester

Base Information

• Chemical Name: 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester
• CAS No.: 128368-81-0
• Molecular Formula: C₄₀H₅₈O₂
• Molecular Weight: 570.899
• Mol file: 128368-81-0.mol

Synonyms:21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester

Chemical Property of 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester

There total 18 articles about 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester 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: 66.0%

diethyl <(2E,4E)-5-phenylpenta-2,4-dienyl>phosphonate (109529-99-9) + methyl 21-(4-formylphenyl)henicosanoate (128368-80-9) → 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester (128368-81-0)

Guidance literature:

With sodium methylate; In tetrahydrofuran; for 0.5h;

DOI:10.1039/c39900000031

Reference yield:

1,20-eicosanediol (7735-43-5) → 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester (128368-81-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 49 percent / 48percent aq. HBr / petroleum ether / 24 h / Heating

2: PPTS / CH₂Cl₂ / 20 h / Ambient temperature

3: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) THF, 30 min

4: 67 percent / BH₃-Me₂S / tetrahydrofuran / 20 h / Ambient temperature

5: 85 percent / 4-(dimethylamino)pyridine, pyridine / CH₂Cl₂ / 20 h / Ambient temperature

6: 95 percent / PPTS / ethanol / 1 h / Heating

7: 87 percent / Jones reagent / acetone

8: 78 percent / diethyl ether; tetrahydrofuran / 0 °C

9: 69 percent / K₂CO₃ / methanol; tetrahydrofuran / 0.75 h / Ambient temperature

10: 76 percent / CrO₃, pyridine / CH₂Cl₂ / 0.25 h / Ambient temperature

11: 66 percent / NaOCH₃ / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; chromium(VI) oxide; dmap; jones reagent; dimethylsulfide borane complex; hydrogen bromide; sodium methylate; pyridinium p-toluenesulfonate; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetone; Petroleum ether;

DOI:10.1016/S0040-4020(01)86422-X

Reference yield:

(2E, 4E)-5-phenylpenta-2,4-dienal (13466-40-5) → 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester (128368-81-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / DIBAH / tetrahydrofuran / 2 h / Ambient temperature

2: PCl₃ / diethyl ether / 1) 0 deg C, 15 min, 2) room temperature, 10 h

3: 7 h / 130 °C

4: 66 percent / NaOCH₃ / tetrahydrofuran / 0.5 h / 0 °C

With sodium methylate; diisobutylaluminium hydride; phosphorus trichloride; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4020(01)86422-X

upstream raw materials:

diethyl <(2E,4E)-5-phenylpenta-2,4-dienyl>phosphonate

methyl 21-(4-formylphenyl)henicosanoate

1,20-eicosanediol

(2E, 4E)-5-phenylpenta-2,4-dienal

Downstream raw materials:

1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine

21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid