4-{(1E,5R)-7-[4-(benzyloxy)phenyl]-5-hydroxyhept-1-en-1-yl}phenol

Base Information

• Chemical Name: 4-{(1E,5R)-7-[4-(benzyloxy)phenyl]-5-hydroxyhept-1-en-1-yl}phenol
• CAS No.: 1401711-90-7
• Molecular Formula: C₂₆H₂₈O₃
• Molecular Weight: 388.507
• Mol file: 1401711-90-7.mol

Synonyms:4-{(1E,5R)-7-[4-(benzyloxy)phenyl]-5-hydroxyhept-1-en-1-yl}phenol

Chemical Property of 4-{(1E,5R)-7-[4-(benzyloxy)phenyl]-5-hydroxyhept-1-en-1-yl}phenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{(1E,5R)-7-[4-(benzyloxy)phenyl]-5-hydroxyhept-1-en-1-yl}phenol

There total 19 articles about 4-{(1E,5R)-7-[4-(benzyloxy)phenyl]-5-hydroxyhept-1-en-1-yl}phenol 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: 68.0%

(3R)-1-[4-(benzyloxy)phenyl]hept-6-en-3-ol (1401711-88-3) + 4-Vinylphenol (2628-17-3,24979-70-2) → 4-{(1E,5R)-7-[4-(benzyloxy)phenyl]-5-hydroxyhept-1-en-1-yl}phenol (1401711-90-7)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 50 ℃; for 4h; Inert atmosphere;

DOI:10.1002/hlca.201200084

Reference yield: 67.0%

(4S)-6-[4-(benzyloxy)phenyl]-4-hydroxyhexanal + [(4-hydroxyphenyl)methylidene]triphenylphosphine (1401711-89-4) → 4-{(1E,5R)-7-[4-(benzyloxy)phenyl]-5-hydroxyhept-1-en-1-yl}phenol (1401711-90-7) + 4-{(1Z,5R)-7-[4-(benzyloxy)phenyl]-5-hydroxyhept-1-en-1-yl}phenol

Guidance literature:

[(4-hydroxyphenyl)methylidene]triphenylphosphine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

(4S)-6-[4-(benzyloxy)phenyl]-4-hydroxyhexanal; In tetrahydrofuran; hexane; at -78 ℃; for 4h; Inert atmosphere;

DOI:10.1002/hlca.201200084

Reference yield:

3-[4-(benzyloxy)phenyl]propan-1-ol (61440-45-7) → 4-{(1E,5R)-7-[4-(benzyloxy)phenyl]-5-hydroxyhept-1-en-1-yl}phenol (1401711-90-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridinium chlorochromate / dichloromethane / 1 h / 20 °C

2.1: n-butyllithium / hexane; tetrahydrofuran / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C / Inert atmosphere

3.2: 1 h / 0 - 20 °C / Inert atmosphere

4.1: (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III) / tetrahydrofuran; water / 24 h / 0 °C

5.1: copper(l) iodide / tetrahydrofuran / 4 h / -78 °C / Inert atmosphere

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / 50 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(l) iodide; n-butyllithium; (acetao)(aqua)(S,S)-N,N′-bis(3,5-di-tert-butylsalicylidene-1,2-cyclohexanediamino)-cobalt(III); 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; water; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination;

DOI:10.1002/hlca.201200084

upstream raw materials:

3-[4-(benzyloxy)phenyl]propan-1-ol

1-(benzyloxy)-4-(but-3-en-1-yl)benzene

2-{2-[4-(benzyloxy)phenyl]ethyl}oxirane

p-benzyloxybenzaldehyde

Downstream raw materials:

4,4'-[(1E,5R)-5-hydroxyhept-1-ene-1,7-diyl]diphenol