(E,E)-1,6-bis(4-methoxyphenyl)-1,5-hexadiene

Base Information

• Chemical Name: (E,E)-1,6-bis(4-methoxyphenyl)-1,5-hexadiene
• CAS No.: 72448-90-9
• Molecular Formula: C₂₀H₂₂O₂
• Molecular Weight: 294.393
• Nikkaji Number: J1.094.828B
• Wikidata: Q76416704
• Metabolomics Workbench ID: 46948
• Mol file: 72448-90-9.mol

Synonyms:(E,E)-1,6-bis(4-methoxyphenyl)-1,5-hexadiene;Ocimin;CHEBI:174113;1-methoxy-4-[(1E,5E)-6-(4-methoxyphenyl)hexa-1,5-dienyl]benzene;1-methoxy-4-[(1E,5E)-6-(4-methoxyphenyl)hexa-1,5-dien-1-yl]benzene;72448-90-9

Chemical Property of (E,E)-1,6-bis(4-methoxyphenyl)-1,5-hexadiene

Chemical Property:

• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 294.161979940
• Heavy Atom Count: 22
• Complexity: 298

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=CCCC=CC2=CC=C(C=C2)OC
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/CC/C=C/C2=CC=C(C=C2)OC

Technology Process of (E,E)-1,6-bis(4-methoxyphenyl)-1,5-hexadiene

There total 11 articles about (E,E)-1,6-bis(4-methoxyphenyl)-1,5-hexadiene 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: 83.0%

(E)-p-methoxy-cinnamyl alcohol (53484-50-7) → 1,6-bis-(p-methoxyphenyl)-1,5-(E),(E)-hexadiene (72448-90-9)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; triphenylphosphine; bis(pinacol)diborane; In acetonitrile; at 50 ℃; for 12h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.0c01424

Reference yield: 67.5%

1,6-bis-(p-methoxyphenyl)-1,6-hexanediol (84092-48-8) → 1,6-bis-(p-methoxyphenyl)-1,5-(E),(E)-hexadiene (72448-90-9)

Guidance literature:

With triphenylphosphine; In tetrachloromethane; dichloromethane; for 6h; Heating;

DOI:10.1080/00397919908086116

Reference yield: 41.0%

[1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide (15546-42-6) + 4-methoxy-benzaldehyde (123-11-5) → 1,6-bis-(p-methoxyphenyl)-1,5-(E),(E)-hexadiene (72448-90-9)

Guidance literature:

With lithium methanolate; In methanol; N,N-dimethyl-formamide; at 90 ℃; for 1h;

upstream raw materials:

t-butyl bromide

1-(p-methoxyphenyl)propenyl-lithium

(E)-1-(4-methoxyphenyl)-3-chloropropene

(hex-5-enyl)magnesium bromide

Refernces

• 1、 Gan, Yi,Hu, Hui,Liu, Yuanhong. "Nickel-Catalyzed Homo- And Cross-Coupling of Allyl Alcohols via Allyl Boronates". supporting information. p. 4418 - 4423. Retrieved 2020/06/27.
• 2、 Khasnis, Dipti S.,Mane, Ramchandra B.. "A ONE-STEP SYNTHESIS OF OCIMIN BY A bis-WITTIG REACTION". . p. 126 - 127. Retrieved 2007/10/03.