Cyclen

Cyclen (1,4,7,10-tetraazacyclododecane) is a aza-crown ether with the formula (CH₂CH₂NH)₄. It is a white solid.

Cyclen

Names
IUPAC name 1,4,7,10-Tetrazacyclododecane
Identifiers
CAS Number	294-90-6
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:37391
ChEMBL	ChEMBL19880
ChemSpider	58488
ECHA InfoCard	100.102.391
PubChem CID	64963
UNII	964584YO2O
CompTox Dashboard (EPA)	DTXSID60183621
InChI InChI=1S/C8H20N4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h9-12H,1-8H2 Key: QBPPRVHXOZRESW-UHFFFAOYSA-N InChI=1/C8H20N4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h9-12H,1-8H2 Key: QBPPRVHXOZRESW-UHFFFAOYAQ
SMILES N1CCNCCNCCNCC1 C1CNCCNCCNCCN1
Properties
Chemical formula	C8H20N4
Molar mass	172.276 g·mol^−1
Appearance	White solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

Crystal structure of a Zn(II) cation coordinated to cyclen and ethanol.[1]

Synthesis

High dilution conditions result in a low reaction rate penalty and this disadvantage is removed in an alternative procedure starting from triethylenetetraamine and dithiooxamide to a bisamidine – also a bis(imidazoline) – followed by reduction and ring expansion with DIBAL.[3]

In one study [4] cyclen is covalently bonded through a propylene molecular spacer to adenine and chelated with zinc diperchlorate. This complex is able to selectively bind uracil and uridine in a 1:2 ratio both through the adenine part and cyclen part of the molecule as evidenced by mass spectrometry.

See also

• Cyclam

References

1. Schrodt, Antje; Neubrand, Anton; Van Eldik, Rudi (1997). "Fixation of CO₂ by Zinc(II) Chelates in Alcoholic Medium. X-ray Structures of {[Zn(cyclen)]₃(μ₃-CO₃)}(ClO₄)₄ and [Zn(cyclen)EtOH](ClO₄)₂". Inorg. Chem. 36 (20): 4579–4584. doi:10.1021/ic961368t. PMID 11670124.
2. Atkins, T. J.; Richman, J. E.; Oettle, W. F. (1978). "1,4,7,10,13,16-Hexaazacyclooctadecane". Org. Synth. 58: 86. doi:10.15227/orgsyn.058.0086.
3. Reed, David P.; Weisman, Gary R. (2002). "1,4,7,10-Tetraazacyclododecane". Org. Synth. 78: 73. doi:10.15227/orgsyn.078.0073.
4. Xia, Chuan-Qin; Tan, Xin-Yu; Chen, Shan-Yong; Yue, Yang; Yu, Xiao-Qi (2006). "The conjugate of adenine–cyclen Zn(II) complex: its synthesis and selective recognition abilities for uracil and uridine" (PDF). Arkivoc. 2: 68–76.

Further reading

• Suchý, M.; Hudson, R. H. E. (2008). "Synthetic Strategies Toward N-Functionalized Cyclens". Eur. J. Org. Chem. 2008 (29): 4847–4865. doi:10.1002/ejoc.200800636.