214078-93-0

Basic information

• Product Name: 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane
• Synonyms: 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane;1,4,8,11-Tetraazacyclotetradecane, 1,8-bis(phenylMethyl)-;1,8-Dibenzylcyclam;trans-N-Dibenzyl-Cyclam
• CAS NO: 214078-93-0
• Molecular Formula: C₂₄H₃₆N₄
• Molecular Weight: 380.57
• Mol File: 214078-93-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 67-68°C
• Boiling Point: 514.1°Cat760mmHg
• Flash Point: 269°C
• Appearance: /
• Density: 1.003g/cm³
• Vapor Pressure: 1.11E-10mmHg at 25°C
• Refractive Index: 1.536
• Sensitive: Hygroscopic
• CAS DataBase Reference: 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane(214078-93-0)
• EPA Substance Registry System: 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane(214078-93-0)

Safety Data

• Hazardous Substances Data: 214078-93-0(Hazardous Substances Data)

Usage

General Description

1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane, also known as Dibenzylcyclen, is a chemical compound with a tetraazamacrocyclic structure. It is widely used in coordination chemistry and medicinal chemistry as a chelating agent for metal ions. Dibenzylcyclen has four nitrogen atoms in its cyclic structure, which allows it to form stable complexes with metal ions such as copper, zinc, and nickel. These complexes have been studied for their potential use in medical imaging, as well as in the treatment of metal ion-related diseases. Additionally, Dibenzylcyclen has been investigated as a potential ligand for catalysis and as a component in the development of new materials with specific properties. Its versatile applications make it a valuable compound in various fields of research and industry.

InChI:InChI=1/C24H36N4/c1-3-9-23(10-4-1)21-27-17-7-13-26-16-20-28(18-8-14-25-15-19-27)22-24-11-5-2-6-12-24/h1-6,9-12,25-26H,7-8,13-22H2

Upstream product

• 100-39-0 benzyl bromide 
• 75920-10-4 1,4,8,11-tetraazatricyclo[9.3.1.14,8]hexadecane 
• 295-37-4 1,4,8,11-Tetraazacyclotetradecane 
• 100-52-7 benzaldehyde 

Downstream Products

• 309253-73-4 Diethyl 4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-1-(methylphosphonate) 
• 309253-74-5 Tetraethyl 4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-1,8-di(methylphosphonate) 
• 1262962-74-2 (Bn₂Cyclam)Zr(NMe₂) 
• 910803-93-9 (1,8-dibenzyl-1,4,8,11-tetraazacyclotetradecane)zirconiumdichloride 
• 1351306-48-3 [((C₆H₅CH₂NC₃H₆NC₂H₄)2)Zr(OC(CH₃)3)2] 
• 1242097-00-2 [(trans-N,N'-dibenzylcyclam)Zr(benzyl)2] 

Relevant articles and documents

CoII Complexes as Liposomal CEST Agents

Three paramagnetic CoII macrocyclic complexes containing 2-hydroxypropyl pendant groups, 1,1′,1′′,1′′′-(1,4,8,11-tetraazacyclotetradecane-1,4,8,11-tetrayl)tetrakis- (propan-2-ol) ([Co(L1)]2+, 1,1′-(4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-1,8-diyl)bis(propan-2-ol) ([Co(L2)]2+), and 1,1′-(4,11-dibenzyl-1,4,8,11-tetraazacyclotetradecane-1,8-diyl)bis(octadecan-2-ol) ([Co(L3)]2+) were synthesized to prepare transition metal liposomal chemical exchange saturation transfer (lipoCEST) agents. In solution, ([Co(L1)]2+) forms two isomers as shown by 1H NMR spectroscopy. X-ray crystallographic studies show one isomer with 1,8-pendants in cis-configuration and a second isomer with 1,4-pendants in trans-configuration. The [Co(L2)]2+ complex has 1,8-pendants in a cis-configuration. Remarkably, the paramagnetic-induced shift of water 1H NMR resonances in the presence of the [Co(L1)]2+ complex is as large as that observed for one of the most effective LnIII water proton shift agents. Incorporation of [Co(L1)]2+ into the liposome aqueous core, followed by dialysis against a solution of 300 mOsm L?1 produces a CEST peak at 3.5 ppm. Incorporation of the amphiphilic [Co(L3)]2+ complex into the liposome bilayer produces a more highly shifted CEST peak at ?13 ppm. Taken together, these data demonstrate the feasibility of preparing CoII lipoCEST agents.

Copper(ii) complexes for cysteine detection using 19F magnetic resonance

Cysteine plays an essential role in maintaining cellular redox homeostasis and perturbations in cysteine concentration are associated with cardiovascular disease, liver disease, and cancer. 19F MRI is a promising modality for detecting cysteine in biology due to its high tissue penetration and negligible biological background signal. Herein we report fluorinated macrocyclic copper complexes that display a 19F NMR/MRI turn-on response following reduction of the Cu(ii) complexes by cysteine. The reactivity with cysteine was studied by monitoring the appearance of a robust diamagnetic 19F signal following addition of cysteine in conjunction with UV-vis and EPR spectroscopies. Importantly, complexes with-CH2CF3 tags display good water solubility. Studies with this complex in HeLa cells demonstrate the applicability of these probes to detect cysteine in complex biological environments.

NOVEL TETRA-AZA MACROCYCLIC COMPOUND, METHOD FOR PREPARING SAME, AND USE THEREOF

Provided are a cross-bridged tetraaza macrocyclic compound of a novel structure that can be used, for example, as a contrast agent for diagnostic imaging or a radiopharmaceutical and a method for preparing the same. The disclosed tetraaza macrocyclic comp