4''-(Pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid methyl ester

Base Information

• Chemical Name: 4''-(Pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid methyl ester
• CAS No.: 158937-30-5
• Molecular Formula: C₂₅H₂₆O₃
• Molecular Weight: 374.48
• Mol file: 158937-30-5.mol

Synonyms:4′′-pentyloxy-[1,1':4',1′′-terphenyl]-4-carboxylic acid methyl ester

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

Chemical Property:

• Density: 1.076±0.06 g/cm3 (20 oC 760 Torr)

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 6 articles about 4''-(Pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxylic acid methyl ester 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: 91.1%

4-(4-n-pentyloxyphenyl)phenylboronic acid (158937-25-8) + methyl 4-iodobenzoate (619-44-3) → 4′′-pentyloxy-[1,1':4',1′′-terphenyl]-4-carboxylic acid methyl ester (158937-30-5)

Guidance literature:

With palladium diacetate; sodium carbonate; triphenylphosphine; In propan-1-ol; toluene; for 4h; Reflux; Inert atmosphere;

DOI:10.1016/j.ejmech.2012.01.054

Reference yield: 45.0%

4-n-pentoxyphenylboronic acid ethylene glycol ester (289706-68-9) + methyl 4’-iodo-[1,1’-biphenyl]-4-carboxylate (158407-15-9) → 4′′-pentyloxy-[1,1':4',1′′-terphenyl]-4-carboxylic acid methyl ester (158937-30-5)

Guidance literature:

With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); at 80 ℃; for 12h;

Reference yield:

4-bromo-4'-hydroxybiphenyl (29558-77-8) → 4′′-pentyloxy-[1,1':4',1′′-terphenyl]-4-carboxylic acid methyl ester (158937-30-5)

Guidance literature:

Multi-step reaction with 3 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

2.3: 0.17 h / 20 °C

3.1: palladium diacetate; sodium carbonate; triphenylphosphine / propan-1-ol; toluene / 4 h / Reflux; Inert atmosphere

With n-butyllithium; palladium diacetate; sodium carbonate; potassium carbonate; triphenylphosphine; In propan-1-ol; tert-butyl methyl ether; toluene; butanone; 3.1: Suzuki reaction;

DOI:10.1016/j.ejmech.2012.01.054

upstream raw materials:

methyl 4-iodobenzoate

4-bromo-4'-pentyloxybiphenyl

4-n-pentoxyphenylboronic acid ethylene glycol ester

methyl 4’-iodo-[1,1’-biphenyl]-4-carboxylate

Downstream raw materials:

C₄₄H₅₈N₄O₉

C₄₅H₆₀N₄O₈

Anidulafungin

2,4,5-trichlorophenyl 4-(4'-pentyloxybiphenyl)benzoate

Refernces

• 1、 Yao, Jianzhong,Liu, Hongming,Zhou, Ting,Chen, Hai,Miao, Zhenyuan,Sheng, Chunquan,Zhang, Wannian. "Total synthesis and structure-activity relationships of new echinocandin-like antifungal cyclolipohexapeptides". supporting information; experimental part. p. 196 - 208. Retrieved 2012/07/28.
• 2、 Debono, Manuel,Turner, William W.,LaGrandeur, Lisa,Burkhadt, Fred J.,Nissen , Jeffrey S.,et al.. "Semisynthetic Chemical Modification of the Antifungal Lipopeptide Echinocandin B (ECB): Structure-Activity Studies of the Lipophilic and Geometric Parameters of Polyarylated Acyl Analogs of ECB". . p. 3271 - 3281. Retrieved 2007/10/02.