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Chemical Structure| 26830-95-5 Chemical Structure| 26830-95-5

Structure of 26830-95-5

Chemical Structure| 26830-95-5

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Product Details of [ 26830-95-5 ]

CAS No. :26830-95-5
Formula : C8H6N2O2
M.W : 162.15
SMILES Code : N#CC1=CC=C(C)C=C1[N+]([O-])=O
MDL No. :MFCD00056107
InChI Key :QGBSLPHQCUIZKK-UHFFFAOYSA-N
Pubchem ID :96235

Safety of [ 26830-95-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302+H312-H331
Precautionary Statements:P261-P302+P352
Class:6.1
UN#:3439
Packing Group:

Computational Chemistry of [ 26830-95-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 44.94
TPSA ?

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

69.61 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.38
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

1.89
Log Po/w (WLOGP)?

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

1.77
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.

0.59
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

0.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.15

Water Solubility

Log S (ESOL):?

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

-2.34
Solubility 0.741 mg/ml ; 0.00457 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.

-2.97
Solubility 0.172 mg/ml ; 0.00106 mol/l
Class?

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

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

-2.24
Solubility 0.931 mg/ml ; 0.00574 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

Yes
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.

-5.95 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

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)

2.01

Application In Synthesis of [ 26830-95-5 ]

* 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 [ 26830-95-5 ]

[ 26830-95-5 ] Synthesis Path-Downstream   1~6

  • 3
  • [ 26830-95-5 ]
  • [ 3847-57-2 ]
  • [ 92424-94-7 ]
  • 4
  • [ 7647-01-0 ]
  • [ 26830-95-5 ]
  • tin [ No CAS ]
  • [ 39549-79-6 ]
  • 5
  • [ 26830-95-5 ]
  • [ 63089-50-9 ]
  • 6
  • [ 26830-95-5 ]
  • [ 153775-42-9 ]
YieldReaction ConditionsOperation in experiment
74.5% With chromium(VI) oxide; periodic acid; In acetonitrile; at 20℃; for 16h;Product distribution / selectivity; Example 17: Alternative preparation of 4-cyano-3-nitro-benzoic acid; Under an inert atmosphere, periodic acid (492 g, 2.17 mol) was dissolved in acetonitrile (7.7 1) with vigorous stirring, and then, after 15 minutes chromium(VI) oxide (25 g, 0.25 mol) and 4-methyl-2-nitro-benzonitrile (100 g, 0.62 mol) were added successively. The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was decanted and the supernatant filtered. The filtrate was concentrated and the residue partitioned between aqueous sodium carbonate (IM) and dichloromethane. The precipitate was isolated by filtration to give 4-cyano-3-nitro-benzoic acid (150 g). The filtrate was extracted twice with dichloromethane and was then acidified by addition of aqueous hydrochloric acid (4N) to pH 1. The acidified filtrate was then extracted three times with dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated. This residue was partitioned between aqueous sodium carbonate (IM) and dichloromethane. The precipitate was isolated by filtration to give 4-cyano-3-nitro-benzoic acid (26.67 g). Total yield: 150 g + 26.67 g = 176.67 g; 74.5 % yield.
With sodium dichromate; sulfuric acid; at 0 - 20℃; for 5h; Example 229: 3-Chloro-benzo[b1thiophene-2-carboxylic acid [5-(4-chloro-phenyl- carbamoyl)-2-(2H-tetrazol-5-yl)phenvHamideTo a solution of 4-cyano-2-nitrotoluene (1 eq.) in 70% sulfuric acid at 0-10C sodium dichromate (1.5 eq.) was added portionwise under stirring, and stirring was continued at room temperature for 5 h. The reaction mixture was poured into crushed ice and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2S04 and evaporated to dryness. The residue was dissolved in dichloromethane, treated with oxalyl chloride (4 eq.) and a catalytic amount of DMF. After stirring at room temperature for 4 h, the solvent was evaporated under vacuum, the residue re-dissolved in dichloromethane and evaporated again to dryness. The residue was dissolved in dichloromethane, treated with triethylamine (1.2 eq.) and 4-chloroaniline (1.2 eq.) and stirred at room temperature for 12 h. After evaporation of solvent under vacuum, the residue was partitioned between water and ethyl acetate. The organic layer was washed with diluted HCI and water, dried over Na2S04 and evaporated under vacuum. The residue was chromatographed over silica gel (15% ethyl acetate - hexane). The collected fractions were evaporated under vacuum to afford 0.38 eq. (38%) of 4'-chloro-4-cyano-3- nitrobenzoylaniline.This product was dissolved in MeOH and hydrogenated for 20 h in the presence of 10% platinum sulfide on carbon. After filtration of the catalyst through a Celite pad, the filtrate was concentrated under vacuum and the residue was dissolved in dry THF. 3-Chloro- thiophene-2-carbonyl chloride was added and the reaction mixture was refluxed for 14 h. The solvent was concentrated under vacuum and the residue was crystallized form ethyl acetate-hexane. The compound obtained (0.25 eq.) was dissolved in DMF and treated with sodium azide (1 eq.) and ammonium chloride (1 eq.) and the reaction mixture was stirred for 24 h at 100C. After cooling, the reaction mixture was diluted with ice cold water. The precipitated solid was collected by suction filtration, washed with water and dried to afford the title compound, mp >250C, in 12% overall yield.1 H-NMR (300 MHz, DMSO-cfe, 300K), delta ppm: 11.68 (s, 1 H, NH); 10.63 (s, 1 H, NH); 8.95 (s, 1 Ar-H); 8.21-7.44 (m, 10 Ar-H); MS: m/z = 507 [M-H]"
 

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