132723-93-4

Usage

Uses

Used in Coordination Chemistry:
Cyclam is utilized as a chelating agent for metal ions in coordination chemistry, due to its ability to form stable complexes with a variety of metal ions. This property makes it valuable for studying metal ion interactions and developing new coordination compounds.
Used in Medical Imaging:
In the medical field, cyclam is studied for its potential applications in medical imaging. Its ability to chelate metal ions can be harnessed to improve the contrast in imaging techniques, aiding in the diagnosis of various conditions.
Used in Drug Delivery:
Cyclam's metal-chelating properties also make it a candidate for drug delivery systems. It can be used to improve the targeting and release of therapeutic agents, enhancing the efficacy and safety of drug treatments.
Used in Catalysis:
In the realm of catalysis, cyclam is explored for its potential to act as a catalyst or to support catalytic processes. Its unique structure and ability to form complexes with metal ions can contribute to the development of new catalytic systems for various chemical reactions.
Used in Chemical Synthesis:
Cyclam's versatility extends to chemical synthesis, where it can be employed as a building block or a template for the synthesis of more complex macrocyclic structures with specific functions and properties.

InChI:InChI=1/C17H30N4/c1-2-6-17(7-3-1)16-21-14-5-10-19-12-11-18-8-4-9-20-13-15-21/h1-3,6-7,18-20H,4-5,8-16H2

Upstream product

• 295-37-4 1,4,8,11-Tetraazacyclotetradecane 
• 100-39-0 benzyl bromide 
• 80799-52-6 Cyclamphosphine oxide 
• 98-88-4 benzoyl chloride 
• 74199-16-9 cis-4,7,11,14-tetraazaperhydropyrene 
• 439211-80-0 cis-9a-methyloctahydro-1H,4H,7H-1,3a,6a,9-tetraazaphenalene 
• 4741-99-5 3,7-diazanonane-1,9-diamine 
• 170161-27-0 1,4,8-tris(tert-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecane 
• 439211-82-2 cis-10b-methyldecahydro-3a,5a,8a,10a-tetraazapyrene 

Downstream Products

• 176252-17-8 Mo(CO)3(C₁₀H₂₃N₄(CH₂C₆H₅)) 
• 578737-58-3 Co⁽²⁺⁾*(C₃H₆)2(C₂H₄)2N₄H₃CH₂C₆H₅*NO₃^(1-)*PF₆^(1-)=[Co((C₃H₆)2(C₂H₄)2N₄H₃CH₂C₆H₅)(NO₃)]PF₆ 
• 578737-62-9 Cd⁽²⁺⁾*(C₃H₆)2(C₂H₄)2N₄H₃CH₂C₆H₅*NO₃^(1-)*PF₆^(1-)=[Cd((C₃H₆)2(C₂H₄)2N₄H₃CH₂C₆H₅)(NO₃)]PF₆ 
• 578737-63-0 [Pb((C₃H₆)2(C₂H₄)2N₄H₃CH₂C₆H₅)(NO₃)2] 

Relevant academic research and scientific papers

Regioselective N-functionalization of tetraazacycloalkanes

Bisaminal type compounds obtained by condensation of pyruvic aldehyde with the suitable open-chain tetraamine followed by cyclization with either dibromoethane or dibromopropane can be regioselectively quaternized by a wide range of alkylating agents. Removal of the bisaminal bridge yields the monosubstituted tetraazamacrocycle or bismacrocycle. Further functionalization allows the preparation of bifunctional ligands or trisubstituted macrocycles. The structure of six compounds was solved by X-ray diffraction, and the unexpected results are rationalized according to the molecular modeling calculations.

An organic template approach for the synthesis of selectively functionalised tetraazacycloalkanes

Selectively functionalised tetraazacycloalkanes are obtained from the open-chain tetraamine by using a bisaminal moiety acting both as a template agent and as a N-protecting group.

A convenient method for the preparation of mono N-alkylated cyclams and cyclens in high yields

Selective and high yield synthesis of mono N-substituted derivatives of cyclam and cyclen can be achieved by using a direct and general synthetic method with very mild reaction conditions.

New macrocyclic ligands. XIII single-ring and tri-linked macrocyclic systems derived from selectively protected cyclam

The synthesis of the four single-ring cyclam derivatives together with the related tri-linked ring derivatives and tetrabenzylated derivative was reported. In the synthesis, differential Boc-protected cyclam derivatives were used as key intermediates. Benzylated and tri-linked cyclam products were found to rely heavily on high-resolution mass spectrometry (HRMS) and all compounds yielded satisfactory HRMS data.

Crystal structures and reactivity of 3a,5a,8a,10a-tetraazaperhydropyrene derivatives. An alternative approach to selective nitrogen alkylation of 1,4,8,11-tetraazacyclotetradecane (cyclam)

1-Alkyl and 1,8-dialkyl-1,4,8,11-tetraazacyclotetradecanes (alkyl = benzyl or methyl) were synthesised through cis-aminal of cyclam which was obtained by reaction of glyoxal and cyclam. The corresponding trans-aminal was synthesised from the respective li

Mono N-alkylation and N-acylation of cyclen and cyclam via their metaltricarbonyl complexes (M=Cr, Mo)

Reaction of metaltricarbonyl complexes of cyclen and cyclam with enolisable aldehydes or acid chlorides yields, after removal of the protecting M(CO3) moiety, selectively mono N-functionalized derivatives.

Mono N-Functionalization of Cyclic and Linear Tetraamines via Their Tridentate Tricarbonylchromium Complexes

The fac-LCr(CO)3 tridentate complexes of 1,4,7,10-tetraazacyclododecane 1, 1,4,8,11-tetraazacyclotetradecane 2, 1,4,7,10-tetraazadecane 3 and 1,5,8,12-tetraazadodecane 4 have been shown selectively alkylated in high yield at the uncomplexed nitrogen atom, giving rise to mono N-functionalized tetraamines and bis-macrocyclic compounds.

General route for the synthesis of mono N-alkylated derivatives of tetraazamacrocycles

The selective synthesis of mono N-substituted derivatives of tetraazamacrocycles can be achieved using a new boron triprotection easily removed after alkylation.