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Chemical Structure| 14691-88-4 Chemical Structure| 14691-88-4

Structure of 4-Amino-tempo
CAS No.: 14691-88-4

Chemical Structure| 14691-88-4

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Product Citations

Product Citations

Diqing Yue ; Weilin Zhang ; Ivy Zhao ; Xiaoting Fang ; Xiaoting Fang ; Yuyue Zhao , et al.

Abstract: Nonaqueous flow batteries hold promise given their high cell voltage and energy density, but their performance is often plagued by the crossover of redox compounds. In this study, we used permselective lithium superionic conducting (LiSICON) ceramic membranes to enable reliable long-term use of organic redox molecules in nonaqueous flow cells. With different solvents on each side, enhanced cell voltages were obtained for a flow battery using viologen-based negolyte and TEMPO-based posolyte molecules. The thermoplastic assembly of the LiSICON membrane realized leakless cell sealing, thus overcoming the mechanical brittleness challenge. As a result, stable cycling was achieved in the flow cells, which showed good capacity retention over an extended test time.

Keywords: nonaqueous flow battery ; organic ; permselectivity ; LiSICON ; stability

Purchased from AmBeed: ; ;

Alternative Products

Product Details of [ 14691-88-4 ]

CAS No. :14691-88-4
Formula : C9H19N2O
M.W : 171.26
SMILES Code : [O]N1C(C)(C)CC(N)CC1(C)C
MDL No. :MFCD00006479

Safety of [ 14691-88-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314-H302+H312+H332
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P362+P364-P403+P233-P501
Class:8
UN#:3263
Packing Group:

Computational Chemistry of [ 14691-88-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 52.49
TPSA ?

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

29.26 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

-4.39
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

0.56
Log Po/w (WLOGP)?

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

0.93
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.

1.15
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

0.23
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.3

Water Solubility

Log S (ESOL):?

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

-1.25
Solubility 9.53 mg/ml ; 0.0556 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-0.75
Solubility 30.7 mg/ml ; 0.179 mol/l
Class?

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

Very 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

-0.96
Solubility 18.7 mg/ml ; 0.109 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

Yes
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

No
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.

-6.95 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

0.0
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

0.0
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

1.0
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

0.0 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<1.0
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)

1.92

Application In Synthesis of [ 14691-88-4 ]

* 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 [ 14691-88-4 ]

[ 14691-88-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 14691-88-4 ]
  • [ 99970-84-0 ]
  • 4,4,'-di(2,2,6,6-tetramethylpiperidin-1-oxyl)diimino-2,2'-bipyridine [ No CAS ]
  • 2
  • [ 6964-21-2 ]
  • [ 14691-88-4 ]
  • 4-thienylacetyl-amino-2,2,6,6-tetramethylpiperidinyl-1-yloxyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.3% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at -10 - 20℃;Inert atmosphere; The monomer TATEMPO was synthesized according to the procedures shown in Scheme 1. A round-bottom flask was filled with 2-(thiophene-3-yl)acetic acid (1.79 g), 4-amino-TEMPO (2.15 g), 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDCl) (2.40 g) and 4-dimethylaminopyridine (DMAP)(1.53 g).Dichloromethane (50mL) was then added. Subsequently, the content of the flask was stirred at-10C under nitrogen atmosphere. Then triethylamine (Et3N) (1.26g) was added dropwise to the above mixture. After addition, the mixture was warmed to room temperature and stirred overnight. The reaction product was washed with dilute hydrochloric acid and saturated sodium carbonate respectively three times and the organic layer dried over sodium sulfate. The resulting product TATEMPO was obtained by column chromatography on silica gel in 73.3% yield.
  • 3
  • [ 51991-94-7 ]
  • [ 14691-88-4 ]
  • (2,2,6,6-tetramethyl-4-[(5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-yl)carbonyl]amino}piperidin-1-yl)oxidanyl [ No CAS ]
 

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Technical Information

Categories

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