1,4,8,11-Tetraazacyclotetradecane-5,7-dione, 6-[(4-nitrophenyl)methyl]-

Base Information

• Chemical Name: 1,4,8,11-Tetraazacyclotetradecane-5,7-dione, 6-[(4-nitrophenyl)methyl]-
• CAS No.: 110912-90-8
• Molecular Formula: C17H25N5O4
• Molecular Weight: 363.417
• DSSTox Substance ID: DTXSID90454836
• Nikkaji Number: J913.909E
• Wikidata: Q82276605
• Mol file: 110912-90-8.mol

Synonyms:110912-90-8;1,4,8,11-Tetraazacyclotetradecane-5,7-dione, 6-[(4-nitrophenyl)methyl]-;DTXSID90454836;6-(4-Nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane-5,7-dione

Chemical Property of 1,4,8,11-Tetraazacyclotetradecane-5,7-dione, 6-[(4-nitrophenyl)methyl]-

Chemical Property:

• XLogP3: 0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 363.19065430
• Heavy Atom Count: 26
• Complexity: 450

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CNCCNC(=O)C(C(=O)NCCNC1)CC2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of 1,4,8,11-Tetraazacyclotetradecane-5,7-dione, 6-[(4-nitrophenyl)methyl]-

There total 2 articles about 1,4,8,11-Tetraazacyclotetradecane-5,7-dione, 6-[(4-nitrophenyl)methyl]- 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: 41.0%

3,7-diazanonane-1,9-diamine (4741-99-5) + diethyl 2-(4-nitrobenzyl)malonate (7598-70-1) → 13-(4-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane-12,14-dione (110912-90-8)

Guidance literature:

In ethanol; for 408h; Heating;

DOI:10.1055/s-1997-1314

Reference yield:

1-bromomethyl-4-nitro-benzene (100-11-8) → 13-(4-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane-12,14-dione (110912-90-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DME, 0 deg C, 0.5 h, 2.) DME, RT, 1 h

2: 41 percent / ethanol / 408 h / Heating

With sodium hydride; In ethanol;

DOI:10.1055/s-1997-1314

Reference yield: 89.0%

13-(4-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane-12,14-dione (110912-90-8) → 13-(4-aminobenzyl)-1,4,8,11-tetraazacyclotetradecane-12,14-dione (850141-56-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; under 2280 Torr;

upstream raw materials:

3,7-diazanonane-1,9-diamine

diethyl 2-(4-nitrobenzyl)malonate

1-bromomethyl-4-nitro-benzene

Downstream raw materials:

13-(4-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane

13-(4-aminobenzyl)-1,4,8,11-tetraazacyclotetradecane-12,14-dione

6-(4-nitrobenzyl)-1,4,8,11-tetraazacyclotetradecane-N,N',N'',N'''-tetraacetic acid tetrabenzyl ester