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Chemical Structure| 102-96-5 Chemical Structure| 102-96-5

Structure of 102-96-5

Chemical Structure| 102-96-5

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Product Details of [ 102-96-5 ]

CAS No. :102-96-5
Formula : C8H7NO2
M.W : 149.15
SMILES Code : O=[N+](/C=C/C1=CC=CC=C1)[O-]
MDL No. :N/A
InChI Key :PIAOLBVUVDXHHL-VOTSOKGWSA-N
Pubchem ID :5284459

Safety of [ 102-96-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P305+P351+P338

Computational Chemistry of [ 102-96-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 44.64
TPSA ?

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

45.82 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.56
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

2.11
Log Po/w (WLOGP)?

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

1.83
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.

1.98
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

0.13
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.52

Water Solubility

Log S (ESOL):?

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

-2.37
Solubility 0.643 mg/ml ; 0.00431 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.

-2.7
Solubility 0.296 mg/ml ; 0.00198 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

-1.85
Solubility 2.11 mg/ml ; 0.0142 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.

-5.71 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)

2.36

Application In Synthesis of [ 102-96-5 ]

* 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 [ 102-96-5 ]

[ 102-96-5 ] Synthesis Path-Downstream   1~27

  • 3
  • [ 102-96-5 ]
  • [ 170384-29-9 ]
  • [ 1088434-15-4 ]
  • [ 1088434-16-5 ]
  • C16H22N2O5 [ No CAS ]
  • 4
  • [ 5585-96-6 ]
  • [ 102-96-5 ]
  • [ 1207551-45-8 ]
  • 5
  • [ 1075-35-0 ]
  • [ 102-96-5 ]
  • [ 1227380-57-5 ]
  • 6
  • [ 1075-34-9 ]
  • [ 102-96-5 ]
  • [ 1227380-58-6 ]
  • 7
  • [ 102-96-5 ]
  • [ 157869-15-3 ]
  • [ 123-54-6 ]
  • C28H23NO2 [ No CAS ]
  • 8
  • [ 102-96-5 ]
  • [ 157869-15-3 ]
  • [ 123-54-6 ]
  • C28H23NO2 [ No CAS ]
  • 9
  • [ 102-96-5 ]
  • [ 5369-19-7 ]
  • [ 123-54-6 ]
  • [ 1600521-17-2 ]
  • 11
  • [ 2568-25-4 ]
  • [ 102-96-5 ]
  • [ 117538-84-8 ]
  • 12
  • [ 42726-73-8 ]
  • [ 102-96-5 ]
  • C16H21NO6 [ No CAS ]
  • C16H21NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C55H44CuF12N7O3S(2+)*2ClO4(1-); triethylamine; In acetonitrile; at 20℃; Examples 1-9 demonstrate the ability to achieve consistent enantiomeric excess in the malonate/nitrostyrene reaction and that the absolute configuration of the product depends only on allosteric consequences of the oxidation state (and thus the propeller helicity of the ligand) and not on counter ion, solvent, concentration, loading, or base. The ability of Delta/Lambda-1 to catalyze the Michael addition of other nitrostyrenes and dimalonate esters was evaluated. All reactions were carried out using the indicated dimalonate ester (0.67 mmol, 2 equiv), the indicated nitrostyrene (0.34 mmol, 1 equiv), and NEt3 (10 mol percent) in MeCN (1 mL) with 5 mol percent catalyst Delta-1 or Lambda-1) at room temperature for 24 hours. The results are shown in Tables 5 and 6 below.
  • 13
  • [ 42726-73-8 ]
  • [ 102-96-5 ]
  • C16H21NO6 [ No CAS ]
  • C16H21NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C55H45CuF12N7O3S(1+)*F6P(1-); triethylamine; In acetonitrile; at 20℃; Examples 1-9 demonstrate the ability to achieve consistent enantiomeric excess in the malonate/nitrostyrene reaction and that the absolute configuration of the product depends only on allosteric consequences of the oxidation state (and thus the propeller helicity of the ligand) and not on counter ion, solvent, concentration, loading, or base. The ability of Delta/Lambda-1 to catalyze the Michael addition of other nitrostyrenes and dimalonate esters was evaluated. All reactions were carried out using the indicated dimalonate ester (0.67 mmol, 2 equiv), the indicated nitrostyrene (0.34 mmol, 1 equiv), and NEt3 (10 mol percent) in MeCN (1 mL) with 5 mol percent catalyst Delta-1 or Lambda-1) at room temperature for 24 hours. The results are shown in Tables 5 and 6 below.
  • 14
  • [ 42726-73-8 ]
  • [ 102-96-5 ]
  • C16H21NO6 [ No CAS ]
  • 15
  • [ 55577-25-8 ]
  • [ 102-96-5 ]
  • 3-(2-nitro-1-phenylethyl)-2-(p-tolyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With acetic acid; In ethanol;Reflux; General procedure: A 5-mL round-bottom flask was charged with indole1(2.0 mmol), β-nitrostyrene2(2.1 mmol), acetic acid (10 μL) and ethanol (1 mL). The mixture was refluxed for 2-8 h, while the reaction progress was monitored by TLC. After complete consumption of the starting material, the mixture was cooled down to room temperature, and the resulting precipitate was collected by filtration. Alternatively, the reaction mixture was concentrated in vacuo, and the residue was purified by preparative column chromatography (eluent EtOAc/Hex 1:4).
  • 16
  • [ 102-96-5 ]
  • [ 14752-66-0 ]
  • [ 16215-12-6 ]
YieldReaction ConditionsOperation in experiment
88% With tris(pyridine-2-carboxylato)manganese(III); In N,N-dimethyl-formamide; at 80℃; for 5h; The specific procedure is as follows: Add nitrophenylethylene (1 mmol) in a round bottom flask (50 ml)P-chlorophenylsulfinate (2 mmol, 2 equiv), Mn (pic) 3 (6 mmol, 6 equiv),Added to DMF, under an open system, magnetic stirring reaction at 80 5h,The reaction solution was extracted with ethyl acetate, the organic layer was washed with saturated brine,Drying anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to give the crude product,The crude product was purified by column chromatography using ethyl acetate / petroleum ether = 1: 5 (V / V) as eluent to give the desired product,The product is a white solid with a yield of 88%.
  • 17
  • [ 19935-81-0 ]
  • [ 102-96-5 ]
  • 1-nitro-4-(4-nitro-3-phenylbutan-2-yl)benzene [ No CAS ]
  • 18
  • [ 1190-39-2 ]
  • [ 102-96-5 ]
  • dibutyl 2-(2-nitro-1-phenylethyl)malonate [ No CAS ]
  • 19
  • [ 102-96-5 ]
  • [ 42182-27-4 ]
  • N-(4-cyanopyridin-2-yl)benzamide [ No CAS ]
  • 20
  • [ 102-96-5 ]
  • [ 39903-01-0 ]
  • [ 174469-41-1 ]
  • 21
  • [ 13138-21-1 ]
  • [ 102-96-5 ]
  • [ 21673-04-1 ]
  • 22
  • [ 32566-01-1 ]
  • [ 102-96-5 ]
  • 6-phenyl-11H-indolo[3,2-c]quinoline [ No CAS ]
  • 23
  • [ 1138-14-3 ]
  • [ 102-96-5 ]
  • 4-nitro-3-phenyl-1-(thiophen-2-yl)butan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With ethanol; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 50℃; for 2h; General procedure: The mixture of 1,3-diarylpropan-1,3-diones 1 (0.5 mmol),nitrostyrenes 2 (0.5 mmol) and DBU (0.05 mmol) in EtOH (3 mL) was stirred at 50 C for 2 h. The reaction wasmonitored by TLC. After the completion of the reaction,the resulting mixture was concentrated under reduced pressure.The residue was isolated by column chromatography using petroleum ether and ethyl acetate (v/v 8:1) aseluent to give the pure product. The analytical datafor products are given in the Supplementary Information section.
  • 24
  • [ 720-94-5 ]
  • [ 102-96-5 ]
  • 4-nitro-1-(4-methylphenyl)-3-phenylbutane-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With sodium acetate; at 20℃; for 24h; General procedure: To a solution of CF3-diketone 2 (1.0 mmol) and NaOAc (0.12 g, 1.5 mmol) in EtOH (5.0 mL) was added nitroalkene 1 (1.0 mmol), and the resulting mixture stirred at room temperature for 24 h. The mixture was concentrated under reduced pressure, washed with H2O (3×3 mL), and the solid that formed was recrystallized from CH2Cl2-hexane (1:2) to give compounds 3a-e or 5a-e as colorless needles. Liquid products 3f-j and 4a were chromatographed on silica gel (eluting with CHCl3).
  • 25
  • [ 102-96-5 ]
  • [ 361456-68-0 ]
  • C15H13NO4 [ No CAS ]
  • 26
  • [ 102-96-5 ]
  • [ 361456-68-0 ]
  • C15H13NO4 [ No CAS ]
  • 27
  • [ 55577-25-8 ]
  • [ 102-96-5 ]
  • (3R*,4′S*)-4′-phenyl-2-(p-tolyl)-4′H-spiro[indole-3,5′-isoxazole] [ No CAS ]
 

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