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Chemical Structure| 122555-91-3 Chemical Structure| 122555-91-3

Structure of DO3A tert-Butyl ester
CAS No.: 122555-91-3

Chemical Structure| 122555-91-3

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Yoon, Bora ; Tai, Kiera Y. ; Thomas, Gawain M. ; Ow, Hooisweng ; Chang, Sehoon ;

Abstract: Chemical tracers are indispensable tools for enhancing reservoir characterization and optimizing production processes in the oil and gas industry. Particularly, interwell water tracers provide key data for efficient water flood management and the improvement of production rates. However, the analysis of these water tracers within reservoir fluids is challenging, requiring laborious separation and extraction steps that often rely on complex instruments and skilled operators. Real-time analysis is especially problematic in remote areas with limited access to well-equipped laboratories. To address these challenges, we introduce a paper-based platform for the time-resolved fluorescence detection of dipicolinic acid (DPA) tracers complexed with terbium ion (Tb3+). Our innovation is driven by the need to simplify tracer analysis, make it portable, and enhance accessibility for oilfield applications. By leveraging the unique properties of cyclen-based macrocyclic ligands, we have achieved the stable and sensitive immobilization of Tb3+ on quartz microfilter paper, eliminating the need for extensive laboratory-based procedures. We achieve the stable and sensitive immobilization of Tb3+ on quartz microfilter paper by leveraging the unique properties of cyclen-based macrocyclic ligands. This innovation enables the formation of highly fluorescent, oil-blind, and optically detectable DPA-Tb3+ complexes at the paper surface. We visualize and capture these fluorescence signals using an intensified charge-coupled device camera via time gating, effectively suppressing undesirable fluorescence originating from crude oil. The quantification of DPA concentrations is achievable down to 158 ppb (9.45 × 10-7 M), as confirmed through time-resolved fluorescence microplate reader measurements. We also demonstrate the practicality of our technology by detecting DPA tracers in the presence of crude oil contamination, a common challenge encountered in oil production wells.

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Product Details of [ 122555-91-3 ]

CAS No. :122555-91-3
Formula : C26H50N4O6
M.W : 514.70
SMILES Code : O=C(OC(C)(C)C)CN1CCN(CC(OC(C)(C)C)=O)CCN(CC(OC(C)(C)C)=O)CCNCC1
MDL No. :MFCD05865261
InChI Key :NMHVTLJFPDOJOD-UHFFFAOYSA-N
Pubchem ID :11237632

Safety of [ 122555-91-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 122555-91-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 36
Num. arom. heavy atoms 0
Fraction Csp3 0.88
Num. rotatable bonds 12
Num. H-bond acceptors 10.0
Num. H-bond donors 1.0
Molar Refractivity 156.1
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

100.65 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

4.64
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.4
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.0
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.93
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.12
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.02

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.75
Solubility 0.0913 mg/ml ; 0.000177 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.16
Solubility 0.036 mg/ml ; 0.0000699 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.88
Solubility 0.0672 mg/ml ; 0.000131 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.74 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

1.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

1.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

4.38

Application In Synthesis of [ 122555-91-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 122555-91-3 ]

[ 122555-91-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 3792-04-9 ]
  • [ 122555-91-3 ]
  • [ 1211942-81-2 ]
  • 2
  • [ 71831-21-5 ]
  • [ 122555-91-3 ]
  • C34H58N4O7 [ No CAS ]
  • 3
  • [ 57280-22-5 ]
  • [ 122555-91-3 ]
  • 1,4,7-tris(tert-butoxycarbonylmethyl)10-(6-hydroxy-2,2-dimethyl-1,3-dioxepane-5yl)-1,4,7,10-tetraazacyclododecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
> 99% With potassium carbonate; In isopropyl alcohol; at 60℃; for 12h; Add 26g to the 1L reaction bottle1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid tert-butyl ester,Potassium carbonate 2g,Isopropyl alcohol 300mL,<strong>[57280-22-5]4,4-dimethyl-3,5,8-trioxabicyclo[5,1,0]octane</strong> 10 g,Reaction at 60 C for 12 h,Recovering isopropyl alcohol,Add 300 mL of toluene,Washing the reaction solution,Dried over anhydrous magnesium sulfate,Isopropyl alcohol is recovered under reduced pressure,Made a pale yellow oil 33g,The yield is greater than 99% and the purity is greater than 99.8%.
 

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