Structure of 102-96-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
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 |
45.82 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.56 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.11 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.83 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.98 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.13 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.52 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.37 |
Solubility | 0.643 mg/ml ; 0.00431 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.7 |
Solubility | 0.296 mg/ml ; 0.00198 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.85 |
Solubility | 2.11 mg/ml ; 0.0142 mol/l |
Class? Solubility class: Log S scale |
Soluble |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.71 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.36 |
* 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.
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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%. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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). |
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