1,5-diphenyl-1,3,5-cyclooctatriene

Base Information

• Chemical Name: 1,5-diphenyl-1,3,5-cyclooctatriene
• CAS No.: 119770-21-7
• Molecular Formula: C₂₀H₁₈
• Molecular Weight: 258.363
• Mol file: 119770-21-7.mol

Synonyms:

Chemical Property of 1,5-diphenyl-1,3,5-cyclooctatriene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-diphenyl-1,3,5-cyclooctatriene

There total 9 articles about 1,5-diphenyl-1,3,5-cyclooctatriene 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:

1,5-diphenyl-3,5-cyclooctadien-1-ol (119770-20-6) → 1,5-diphenyl-1,3,5-cyclooctatriene (119770-21-7) + 2,6-diphenyl-1,3,6-cyclooctatriene (119770-27-3)

Guidance literature:

With pyridine; thionyl chloride; In diethyl ether; at 0 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1021/jo00271a017

Reference yield:

1,5-cis,cis-cyclooctadiene (1552-12-1,111-78-4) → 1,5-diphenyl-1,3,5-cyclooctatriene (119770-21-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) BH₃*THF, 2.) aq. NaOH, 30percent H₂O₂ / 1.) THF, reflux, 1 h, 2.) reflux

2: pyridinium chlorochromate / CH₂Cl₂ / 24 h / Heating

3: 93 percent / tetrahydrofuran; pentane; diethyl ether / 1 h

4: 77 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

5: 1.) LDA, 2.) Br₂ / 1.) pentane, THF, 15 min, 2.) THF

6: 16 percent / tetrahydrofuran; diethyl ether; pentane / -78 - 20 °C

7: 99 percent / NaHCO₃, NaIO₄ / methanol; H₂O / 25 h

8: 500 mg / toluene / 36 h / Heating

9: pyridine, thionyl chloride / diethyl ether / 1 h / 0 °C

With pyridine; sodium hydroxide; sodium periodate; thionyl chloride; borane-THF; dihydrogen peroxide; bromine; sodium hydrogencarbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; pentane; benzene;

DOI:10.1021/jo00271a017

Reference yield:

cyclooctane-1,5-diol (55343-44-7) → 1,5-diphenyl-1,3,5-cyclooctatriene (119770-21-7)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridinium chlorochromate / CH₂Cl₂ / 24 h / Heating

2: 93 percent / tetrahydrofuran; pentane; diethyl ether / 1 h

3: 77 percent / p-toluenesulfonic acid / benzene / 2 h / Heating

4: 1.) LDA, 2.) Br₂ / 1.) pentane, THF, 15 min, 2.) THF

5: 16 percent / tetrahydrofuran; diethyl ether; pentane / -78 - 20 °C

6: 99 percent / NaHCO₃, NaIO₄ / methanol; H₂O / 25 h

7: 500 mg / toluene / 36 h / Heating

8: pyridine, thionyl chloride / diethyl ether / 1 h / 0 °C

With pyridine; sodium periodate; thionyl chloride; bromine; sodium hydrogencarbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; pentane; benzene;

DOI:10.1021/jo00271a017

upstream raw materials:

1,5-diphenyl-3,5-cyclooctadien-1-ol

1,5-cis,cis-cyclooctadiene

cyclooctane-1,5-diol

cyclooctane-1,5-dione