4-Methoxy-4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-2,5-cyclohexadien-1-one

Base Information

• Chemical Name: 4-Methoxy-4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-2,5-cyclohexadien-1-one
• CAS No.: 134904-87-3
• Molecular Formula: C₁₃H₇F₁₃O₂
• Molecular Weight: 442.177
• DSSTox Substance ID: DTXSID101131867
• Mol file: 134904-87-3.mol

Synonyms:SCHEMBL9314828;RRVBPQSCUPZMQI-UHFFFAOYSA-N;DTXSID101131867;4-Methoxy-4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-2,5-cyclohexadien-1-one;134904-87-3;4-methoxy-4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)cyclohexa-2,5-dien-1-one

Chemical Property of 4-Methoxy-4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-2,5-cyclohexadien-1-one

Chemical Property:

• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 442.0238456
• Heavy Atom Count: 28
• Complexity: 671

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1(C=CC(=O)C=C1)C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F

Technology Process of 4-Methoxy-4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-2,5-cyclohexadien-1-one

There total 3 articles about 4-Methoxy-4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)-2,5-cyclohexadien-1-one 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:

n-perfluorohexyl iodide (355-43-1) → 4-methoxy-4-(perfluorohexyl)-2,5-cyclohexadien-1-one (134904-87-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / MeLi-LiBr / diethyl ether / 1) -78 deg C, 30 min, 2) -78 deg C to RT

2: 1) Nu₄NHSO₄, 50percent NaOH / 1) toluene, 10 min, 2) 2h

With sodium hydroxide; Nu₄NHSO₄; methyllithium; lithium bromide; In diethyl ether;

DOI:10.1021/jo00018a055

Reference yield:

p-benzoquinone (106-51-4) → 4-methoxy-4-(perfluorohexyl)-2,5-cyclohexadien-1-one (134904-87-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / MeLi-LiBr / diethyl ether / 1) -78 deg C, 30 min, 2) -78 deg C to RT

2: 1) Nu₄NHSO₄, 50percent NaOH / 1) toluene, 10 min, 2) 2h

With sodium hydroxide; Nu₄NHSO₄; methyllithium; lithium bromide; In diethyl ether;

DOI:10.1021/jo00018a055

Reference yield:

4-hydroxy-4-(perfluorohexyl)-2,5-cyclohexadien-1-one (114934-90-6) + dimethyl sulfate (77-78-1) → 4-methoxy-4-(perfluorohexyl)-2,5-cyclohexadien-1-one (134904-87-3)

Guidance literature:

With sodium hydroxide; Nu₄NHSO₄; Yield given. Multistep reaction; 1) toluene, 10 min, 2) 2h;

DOI:10.1021/jo00018a055

upstream raw materials:

4-hydroxy-4-(perfluorohexyl)-2,5-cyclohexadien-1-one

dimethyl sulfate

n-perfluorohexyl iodide

p-benzoquinone

Downstream raw materials:

ethyl 2-<4-methoxy-4-(perfluorohexyl)-2,5-cyclohexadienylidene>propionate

2-<4-(perfluorohexyl)phenyl>propionic acid

ethyl 2-<4-(perfluorohexyl)phenyl>propionate