Structure of 2-Vinylnaphthalene
CAS No.: 827-54-3
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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. : | 827-54-3 |
Formula : | C12H10 |
M.W : | 154.21 |
SMILES Code : | C=CC1=CC=C2C=CC=CC2=C1 |
MDL No. : | MFCD00004125 |
InChI Key : | KXYAVSFOJVUIHT-UHFFFAOYSA-N |
Pubchem ID : | 13230 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H371 |
Precautionary Statements: | P260-P264-P270-P308+P311-P405-P501 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 10 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 54.04 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.37 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.27 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.37 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.75 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.83 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.72 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.04 |
Solubility | 0.0142 mg/ml ; 0.0000919 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.98 |
Solubility | 0.0161 mg/ml ; 0.000104 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.5 |
Solubility | 0.00484 mg/ml ; 0.0000314 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
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) |
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 |
-4.21 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
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 |
2.0 |
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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.17 |
* 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 |
---|---|---|
82% | General procedure: A sealed tube equipped with a magnetic stirring bar was charged with styrene 1 (1.0mmol), NBS (2.0 mmol) and water (2.0mL) at room temperature. The resulting mixture was heated to 80 °C for 2h. After disappearance of the reactant (monitored by TLC), reaction mixture was cooled to room temperature. To this reaction mixture molecular iodine (2.2 mmol) and 30percent aq. ammonia solution or n-butylamine (10 mmol) were added and it was heated to 80 °C for 1h. After completion of the reaction (monitored by TLC), saturated Na2S2O3 solution (10 mL) was added to the reaction mixture, and it was extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine solution (10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue obtained was purified by column chromatography on 60?120 mesh silica gel using ethyl acetate: n-hexane (1:2) as the eluent to obtain the corresponding aromatic amide 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 6h;Inert atmosphere; | General procedure: Amixture of styrene (6a) (2 mmol, 208 mg), alpha-trifluoromethylacrylic acid (2) (0.5mmol, 70 mg), [Cp*RhCl2]2 (0.005 mmol, 3 mg), AgOAc (1 mmol, 167 mg) and1-methylnaphthalene (ca. 40 mg) as internal standard was stirred in NMP (2.5ml) under argon at 120 C for 6h. Then the reaction mixture was diluted byethyl acetate (30 ml). The organic layer was washed by 1 N HCl (30 ml), water30 (ml), and brine (30 ml) and dried over Na2SO4. After evaporation of thesolvents under vacuum, product 7a (101 mg, 93%) was isolated by columnchromatography on silica gel using hexane/EtOAc/AcOH=90/9/1 (v/v/v) as eluent. |