ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate

Base Information

• Chemical Name: ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate
• CAS No.: 1381949-73-0
• Molecular Formula: C₂₆H₃₂N₂O₄
• Molecular Weight: 436.551
• Mol file: 1381949-73-0.mol

Synonyms:ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate

Chemical Property of ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate

There total 7 articles about ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate 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: 85.0%

4-[(N-tert-butyloxycarbonylamino)methyl]iodobenzene (189132-01-2) + tert-butyl N-(4-ethynylbenzyl)carbamate (680190-96-9) → ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate (1381949-73-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In toluene; at 60 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jo300907r

Reference yield: 34.0%

tert-butyl N-(4-bromobenzyl)carbamate (68819-84-1) + tert-butyl N-(4-ethynylbenzyl)carbamate (680190-96-9) → ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate (1381949-73-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In tetrahydrofuran; at 85 ℃; for 36h; Inert atmosphere;

DOI:10.1002/chem.201605092

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate (1381949-73-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / toluene / 24 h / 60 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; toluene; 2: Sonogashira coupling;

DOI:10.1021/jo300907r

upstream raw materials:

di-tert-butyl dicarbonate

p-iodobenzylamine hydrochloride

4-[(N-tert-butyloxycarbonylamino)methyl]iodobenzene

tert-butyl N-(4-ethynylbenzyl)carbamate

Refernces

• 1、 von Krbek, Larissa K. S.,Achazi, Andreas J.,Schoder, Stefan,Gaedke, Marius,Biberger, Tobias,Paulus, Beate,Schalley, Christoph A.. "The Delicate Balance of Preorganisation and Adaptability in Multiply Bonded Host–Guest Complexes". . p. 2877 - 2883. Retrieved 2017/03/08.