Structure of 90-96-0
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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. : | 90-96-0 |
Formula : | C15H14O3 |
M.W : | 242.27 |
SMILES Code : | COC1=CC=C(C=C1)C(=O)C1=CC=C(OC)C=C1 |
MDL No. : | MFCD00008404 |
InChI Key : | RFVHVYKVRGKLNK-UHFFFAOYSA-N |
Pubchem ID : | 7032 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.13 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 69.3 |
TPSA ? Topological Polar Surface Area: Calculated from |
35.53 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.77 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.57 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.93 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.24 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.44 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.99 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.82 |
Solubility | 0.0366 mg/ml ; 0.000151 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.0 |
Solubility | 0.0241 mg/ml ; 0.0000996 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.12 |
Solubility | 0.00182 mg/ml ; 0.0000075 mol/l |
Class? Solubility class: Log S scale |
Moderately 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) |
Yes |
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) |
Yes |
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 |
-5.24 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 |
0.0 |
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) |
1.53 |
* 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 |
---|---|---|
2.6 g | General procedure: The appropriate Grignard reagent (1.3 equiv) generated according to GP 1 was added to ketone 15 (1.0 equiv) suspended in THF (2mL/mmol) and heated to 60C for 2h. At 25C the mixture was quenched with saturated aqueous NH4Cl solution and extracted with Et2O. The organic phases were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by recrystallization or by column chromatography over silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tetrabutylammonium perchlorate; triethylamine; In tetrahydrofuran; at 20℃;Inert atmosphere; Electrochemical reaction; | General procedure: A 0.3M solution of Bu4NClO4 in THF (15 mL) was placed in thecathodic chamber of a divided cell (40 mL beaker, 3 cm diameter, 6 cm height)equipped with a lead cathode (5 X 5 cm2), a platinum anode (2 X 1 cm2),and a ceramic cylindrical diaphragm (1.5 cm diameter). A 0.3 M solution of Et4NOTsin DMF (4 mL) was placed in the anodic chamber (inside the diaphragm). 1,3-Dimethylpyrimidine-2,4(1H,3H)-dione(1a) (140 mg, 1.0 mmol), benzophenone (2a) (368mg, 2.0 mmol), TMSCl (0.64 mL, 5 mmol), and TEA (0.70 mL, 5 mmol) were added tothe cathodic chamber. After 400 C of electricity was passed at a constantcurrent of 200 mA at room temperature under nitrogen atmosphere, the catholytewas evaporated in vacuo. The residue was dissolved in diethyl ether (20 mL)and insoluble solid was filtered off. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel(hexanes-EtOAc) to give 3a (305 mg) in 77% yield. |
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