Structure of 6668-24-2
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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. : | 6668-24-2 |
Formula : | C11H12O2 |
M.W : | 176.21 |
SMILES Code : | CC(C(C)C(C1=CC=CC=C1)=O)=O |
MDL No. : | MFCD09033549 |
InChI Key : | IRNJRGVFXLVQEK-UHFFFAOYSA-N |
Pubchem ID : | 569369 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.27 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 51.26 |
TPSA ? Topological Polar Surface Area: Calculated from |
34.14 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.73 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.11 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.09 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.68 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.58 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.04 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.41 |
Solubility | 0.693 mg/ml ; 0.00393 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.46 |
Solubility | 0.614 mg/ml ; 0.00349 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.11 |
Solubility | 0.136 mg/ml ; 0.000769 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 |
-5.88 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 |
1.0 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) |
1.51 |
* 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 |
---|---|---|
85% | General procedure: Appropriate beta-diketone (100 mmol) was dissolved in anhydrous acetone (80 mL). Subsequently, anhydrous potassium carbonate (93 mmol) was added under inert. After stirring the solution for 5 min. at room temperature, methyl iodide (7.72 mL, 100 mmol) was added dropwise during 10 min. The reaction mixture was then refluxed for 12 h. Volatile components were distilled off, the residue was diluted with ether (100 mL) and precipitated solid was removed by suction. The filtrate was evaporated in vacuo and the residue was further purified. | |
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h; | To a mixture of the benzoylacetone (1a) (2.0 mmol) and iodomethane (2.2 mmol) in N,N-dimethylformamide (5.0 mL) was added K2CO3 (1.5 mmol) at room temperature. The resulting reaction mixture was stirred at room temperature for 18 h. The reaction was then quenched with H2O (50 mL) and extracted with EtOAc (3 × 50 mL). The combined organic layers were washed with brine (30 mL), dried over MgSO4 , filtered, and concentrated (aspirator). The residue was purified by column chromatography. |