Structure of 2-Nitrobenzyl alcohol
CAS No.: 612-25-9
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 612-25-9 |
Formula : | C7H7NO3 |
M.W : | 153.14 |
SMILES Code : | C1=CC=CC(=C1CO)[N+](=O)[O-] |
MDL No. : | MFCD00007186 |
InChI Key : | BWRBVBFLFQKBPT-UHFFFAOYSA-N |
Pubchem ID : | 11923 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 41.39 |
TPSA ? Topological Polar Surface Area: Calculated from |
66.05 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.99 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.24 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.94 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.34 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.49 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.6 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.84 |
Solubility | 2.2 mg/ml ; 0.0144 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.22 |
Solubility | 0.912 mg/ml ; 0.00596 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.59 |
Solubility | 3.92 mg/ml ; 0.0256 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 |
No |
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) |
No |
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 |
-6.35 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) |
1.58 |
* 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 |
---|---|---|
44% | With 1,1'-bis-(diphenylphosphino)ferrocene; formic acid; N-ethyl-N,N-diisopropylamine; In toluene; at 150℃; for 24h;Inert atmosphere; | General procedure: The mixture of 2-nitrobenzyl alcohol 1a-f (0.5 mmol), alcohol 2a-k (0.6 mmol), HCO2H (53 muL, 1.0 mmol), DIPEA (125 muL, 0.75 mmol), and dppf (14.1 mg, 0.025 mmol) in toluene (1.0 mL) was stirred at 150C (screw-capped vial) for 1 d under argon, cooled to r.t., then water (5mL) was added. The two layers were separated, and the aqueous phase was extracted with EtOAc (3 × 10 mL). The combined organic extracts were washed by brine, dried (anhyd Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel (100-200 mesh) to afford the desired quinoline 3a-r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10 mg | With 1,4-diaza-bicyclo[2.2.2]octane; sulfur; urea; In dimethyl sulfoxide; at 140℃; for 8h; | General procedure: To a 4-mL screw-cap vial was added 2-nitrobenzyl alcohol (15.3 mg, 0.1 mmol), phenylacetic acid (34.0 mg, 0.25 mmol), base, elemental sulfur, urea, and DMSO (0.3 mL).The reaction tube was tightly capped and the resulting mixture was then stirred at a given temperature. After completion of the reaction, the mixture was cooled to room temperature and diphenyl ether (17.2 mg, 0.1 mmol) as an internal standard was added. The organic components were then extracted into ethyl acetate (3×2 mL), washed with NaHCO3 solution (10% in water, 3×1 mL), dried over anhydrous Na2SO4, filtered, and analyzed by GC with reference to diphenyl ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tetraethylammonium iodide; acetic acid; In dichloromethane; at 20℃; for 24h;UV-irradiation; | Add 0.2mmol of indoline compound V into the 10mL reaction tube,Add 0.4mmol of o-nitrobenzyl alcohol compound VI, 0.2mmol of acetic acid, 0.2mmol of tetraethylammonium iodide, 4mL of dichloromethane, and irradiate with 385-405nm ultraviolet light at room temperature.Reaction for 24h. After the reaction, it is separated by column chromatography to obtainN-(2-arylcarboxaldehyde)-1-aminoindole derivative (R1=5-fluoro, R2=hydrogen) to obtain a brown jelly with a yield of 79%. |
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