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Chemical Structure| 1121-13-7 Chemical Structure| 1121-13-7

Structure of 1121-13-7

Chemical Structure| 1121-13-7

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Product Details of [ 1121-13-7 ]

CAS No. :1121-13-7
Formula : C3H2N2O3
M.W : 114.06
SMILES Code : [N+](=O)([O-])C1=CON=C1
MDL No. :MFCD06638027
InChI Key :LLLMLGQOFWRRTH-UHFFFAOYSA-N
Pubchem ID :11332437

Safety of [ 1121-13-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 1121-13-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 5
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 25.32
TPSA ?

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

71.85 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.75
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

0.2
Log Po/w (WLOGP)?

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

0.58
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.

-1.62
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

-0.99
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.21

Water Solubility

Log S (ESOL):?

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

-1.07
Solubility 9.72 mg/ml ; 0.0852 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.

-1.27
Solubility 6.16 mg/ml ; 0.054 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

-0.56
Solubility 31.2 mg/ml ; 0.274 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

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

No
Log Kp (skin permeation)?

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

-6.85 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

2.0
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

2.0 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)

2.47

Application In Synthesis of [ 1121-13-7 ]

* 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 [ 1121-13-7 ]

[ 1121-13-7 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 288-14-2 ]
  • [ 1121-13-7 ]
YieldReaction ConditionsOperation in experiment
44% With ammonium nitrate; trifluoroacetic anhydride; at 25 - 30℃; To the solution of 4a (Ig, 14.5mmol) in trifluoroacetic anhydride (7mL, 50.7mmol) was added ammonium nitrate (1.8g, 22.5mmol) in 0.3g each portion, keeping the reaction temperature between 25-3O0C. After the addition was complete, the mixture was poured into ice water and extracted with DCM (15mLx4). The extract was washed with water and the aqueous layer was extracted with DCM. The combined DCM extract was dried over MgSO4, filtered and concentrated to give a yellow green oil. The oil was triturated by hexane (cooled to 50C) to provide a solid which was filtered to provide 4b (0.72g, 44%).
With ammonium nitrate; trifluoroacetic anhydride; at 25 - 30℃; Isoxazole (4.64 ml, 72.4 mmol) was dissolved in trifluoroacetic anhydride (30 ml) and ammonium nitrate (6.37 g, 80 mmol) was added in 0.5 g portions, keeping the reaction temperature between 25C~30C. Another batch of ammonium nitrate (3.6 g) was then added. About one third of the reaction solution was poured onto ice water, and extracted with dichloromethane (60 ml x4 ). The extracts were combined, washed with water (80 ml x 3), dried over anhydrous MgS04, and concentrated to yield the title compound as a yellow solid. 0.9 g.
  • 2
  • [ 1121-13-7 ]
  • [ 64-17-5 ]
  • [ 62-53-3 ]
  • [ 6123-71-3 ]
  • 3
  • [ 1121-13-7 ]
  • [ 62-53-3 ]
  • [ 6123-71-3 ]
  • 4
  • [ 1121-13-7 ]
  • [ 62-53-3 ]
  • [ 98589-79-8 ]
  • 5
  • [ 1121-13-7 ]
  • [ 97925-51-4 ]
  • 6
  • [ 1121-13-7 ]
  • [ 108511-97-3 ]
YieldReaction ConditionsOperation in experiment
With ammonium chloride; zinc; In water; at 0 - 5℃; for 2h; 4- Nitroisoxazole (may be prepared as described in Description 94; 850 mg, 7.45 mmol) was added to a solution of ammonium chloride (9169 mg, 171 mmol) in water (60 ml). The resultant suspension was cooled to 0°C, and zinc (4142 mg, 63.3 mmol) was added in portions whilst keeping the temperature below 5°C. After the addition, the mixture was stirred at 0-5°C for 2 hours. The reaction mixture was then filtered, and the filtrate was extracted with ethyl acetate (100 ml x 4). The organic phase was washed by water (100 ml x 2), dried over anhydrous MgS04, and concentrated to yield the title compound as a brown oil, 535 mg.
  • 9
  • sodium salt of nitromalondialdehyde [ No CAS ]
  • [ 1121-13-7 ]
  • 10
  • [ 1121-13-7 ]
  • [ 64-17-5 ]
  • [ 100-63-0 ]
  • [ 7803-49-8 ]
  • [ 3994-48-7 ]
  • 11
  • [ 181294-57-5 ]
  • [ 1121-13-7 ]
  • 12
  • [ 1121-13-7 ]
  • isoxazol-4-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% To a solution of 4b (200mg, 1.75mmol) in con. HCl (9mL) was added SnCl2.2H2O (1.98g, 8.77mmol). The mixture was stirred at rt for 1.5h, then adjusted by SaLNa2CO3 to pH=8~9 and filtered. The water phase was extracted with EA (30x4) and the combined extract was dried over anhydrous Na2SO4 and filtered. 5OmL of HClZEt2O solution was added to the filtrate and stirred for 30 min then evaporated to dryness to give 4c (125mg, 59%).
Step 1: lsoxazol-4-amine Hydrochloride (bbb-1); To a solution of NH4CI (317g, 5.93 mol) in water (1.4 L) was added <strong>[1121-13-7]4-nitroisoxazole</strong> (30.9 g, 0.26 mol; 95% purity; Reiter, L. A.; J. Org. Chem.; 1987; 52; 2714-2726). The resultant suspension was cooled to 0 C, and Zn (143 g, 2.20 mol) added in portions (0.5-1 g) to keep the temperature below 5C (an ice bath). After about 40% of Zn was added, the exotherm apparently subsided. After the Zn addition was completed, the mixture was stirred at ^0G for 10h, the cooling bath was removed, allowed to warm to ambient temperature, and ethyl acetate (1750 mL) was carefully added dropwise under vigorous stirring. Then the mixture was filtered to remove zinc salts (Caution: leftover Zn reacted exothermically on the filter), and the organic layer was separated. The aqueous layer was extracted with «thyl acetate. The combined organic layers were dried over MgSO4 and evaporated under reduced pressure to give an oily product (13.0 g), which was mixed with 4M HCI in dioxane (50 mL) and kept in a refrigerator overnight. The resultant precipitate was separated by filtration, washed with absolute ether (50 mL), and air-dried to give a light-brown solid in 48 yield % (15.1 g), which was used without further purification or characterization.
 

Historical Records

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