TRI-T-BUTYL 1 4 7 10-TETRAAZACYCLODODECA Chemical Properties

Melting point:

181-183℃

Boiling point:

561.6±50.0 °C(Predicted)

Density 

1.022

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Low-Melting Solid

pka

9.57±0.20(Predicted)

color 

White to Off-White

Sensitive 

Hygroscopic

InChI

InChI=1S/C26H50N4O6/c1-24(2,3)34-21(31)18-28-12-10-27-11-13-29(19-22(32)35-25(4,5)6)15-17-30(16-14-28)20-23(33)36-26(7,8)9/h27H,10-20H2,1-9H3

InChIKey

NMHVTLJFPDOJOD-UHFFFAOYSA-N

SMILES

N1(CC(OC(C)(C)C)=O)CCNCCN(CC(OC(C)(C)C)=O)CCN(CC(OC(C)(C)C)=O)CC1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

29339900

TRI-T-BUTYL 1 4 7 10-TETRAAZACYCLODODECA Usage And Synthesis

Uses

Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetate with amide ligands bearing positively charged terbium complexes are used for sensitive detection of NADPH-dependent enzyme activities.

Synthesis

Under nitrogen protection, 1,4,7,10-tetraazacyclododecane (1 g, 5.81 mmol) was dissolved in anhydrous acetonitrile (20 ml) and cooled to 0 °C. Sodium bicarbonate (1.464 g, 17.44 mmol) was added to the reaction system under stirring conditions. Subsequently, anhydrous acetonitrile solution (10 ml) of tert-butyl bromoacetate (3.4 g, 17.44 mmol) was slowly added through a dropping funnel over a period of 1 hour. The reaction mixture was continued to be stirred at 0 °C for 3 h, followed by raising to room temperature and stirring for 45 h. The progress of the reaction was monitored by thin layer chromatography (TLC) with the unfolding agent being dichloromethane (DCM): methanol (9:1), and the target product had an Rf value of 0.67. Upon completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being dichloromethane solution containing 2% methanol to afford tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7-triacetate (Compound 2) as a white powder in 83.5% yield.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 8, p. 918 - 920
[2] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4459 - 4462
[3] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 12 - 20
[4] Patent: WO2014/200872, 2014, A1. Location in patent: Page/Page column 73; 77
[5] Organic and Biomolecular Chemistry, 2011, vol. 9, # 5, p. 1591 - 1599

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