4''-(Hexyloxy)[1,1':4',1''-terphenyl]-4-carboxylic acid

Base Information

• Chemical Name: 4''-(Hexyloxy)[1,1':4',1''-terphenyl]-4-carboxylic acid
• CAS No.: 158938-09-1
• Molecular Formula: C₂₅H₂₆O₃
• Molecular Weight: 374.48
• DSSTox Substance ID: DTXSID301203715
• Mol file: 158938-09-1.mol

Synonyms:SCHEMBL2354189;DTXSID301203715;4''-(Hexyloxy)[1,1':4',1''-terphenyl]-4-carboxylic acid;158938-09-1

Chemical Property of 4''-(Hexyloxy)[1,1':4',1''-terphenyl]-4-carboxylic acid

Chemical Property:

• XLogP3: 7.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 374.18819469
• Heavy Atom Count: 28
• Complexity: 439

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCOC1=CC=C(C=C1)C2=CC=C(C=C2)C3=CC=C(C=C3)C(=O)O

Technology Process of 4''-(Hexyloxy)[1,1':4',1''-terphenyl]-4-carboxylic acid

There total 2 articles about 4''-(Hexyloxy)[1,1':4',1''-terphenyl]-4-carboxylic acid 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: 86.0%

4-bromo-4'-(n-hexyl-1-oxy)-1,1'-biphenyl (63619-64-7) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → 4''-hexyloxy-[1,1':4',1'']terphenyl-4-carboxylic acid (158938-09-1)

Guidance literature:

With NaOH; potassium carbonate; Pd(PPh₃)4; In 1,4-dioxane; ethanol; water; toluene;

Reference yield:

4-bromo-4'-hydroxybiphenyl (29558-77-8) → 4''-hexyloxy-[1,1':4',1'']terphenyl-4-carboxylic acid (158938-09-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / butanone / 8 h / Reflux

2.1: n-butyllithium / tert-butyl methyl ether / 2 h / -20 °C / Inert atmosphere

2.2: -60 - 20 °C / Inert atmosphere

2.3: 0.17 h / 20 °C

3.1: palladium diacetate; sodium carbonate; triphenylphosphine / water; isopropyl alcohol; toluene / 4 h / Inert atmosphere; Reflux

4.1: cetyltrimethylammonim bromide; potassium hydroxide / 5,5-dimethyl-1,3-cyclohexadiene; water / 3 h / Reflux

4.2: pH 1

With n-butyllithium; cetyltrimethylammonim bromide; palladium diacetate; sodium carbonate; potassium carbonate; triphenylphosphine; potassium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; tert-butyl methyl ether; water; isopropyl alcohol; toluene; butanone; 3.1: Suzuki coupling;

DOI:10.1016/j.tet.2012.02.015

Reference yield:

benzotriazol-1-ol (2592-95-2) + 4''-hexyloxy-[1,1':4',1'']terphenyl-4-carboxylic acid (158938-09-1) → C31H29N3O3

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 48h;

DOI:10.1016/j.tet.2012.02.015

upstream raw materials:

4-bromo-4'-(n-hexyl-1-oxy)-1,1'-biphenyl

4-methoxycarbonylphenylboronic acid

4-bromo-4'-hydroxybiphenyl

Downstream raw materials:

4''-Hexyloxy-[1,1';4',1'']terphenyl-4-carboxylic acid 2,4,5-trichloro-phenyl ester

Nδ-Boc-Orn(Nα-4''-hexyloxy-terphenyl-4-formyl)-Thr-Pro-OMe

Nδ-Boc-Orn(Nα-4''-hexyloxy-terphenyl-4-formyl)-Val-Pro-OMe

cyclo-[Orn(Nα-4''-hexyloxy-terphenyl-4-formyl)-Val-Pro-hTyr-Orn(Nδ-Cbz)-Pro(4S-N3)]