Structure of Ethyl phenylcyanoacetate
CAS No.: 4553-07-5
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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. : | 4553-07-5 |
Formula : | C11H11NO2 |
M.W : | 189.21 |
SMILES Code : | O=C(OCC)C(C#N)C1=CC=CC=C1 |
MDL No. : | MFCD00001866 |
InChI Key : | SXIRJEDGTAKGKU-UHFFFAOYSA-N |
Pubchem ID : | 95298 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.27 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 51.67 |
TPSA ? Topological Polar Surface Area: Calculated from |
50.09 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.07 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.07 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.86 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.61 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.1 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.94 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.37 |
Solubility | 0.806 mg/ml ; 0.00426 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.75 |
Solubility | 0.336 mg/ml ; 0.00177 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.02 |
Solubility | 0.183 mg/ml ; 0.000966 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 |
-5.98 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 |
0.0 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) |
2.24 |
* 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 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea; In 5,5-dimethyl-1,3-cyclohexadiene; at 20℃; for 7h; | General procedure: A solution of α-phenyl cyanoacetates 1a (22.7 mg, 0.12 mmol), maleimide 1b (17.3 mg, 0.10 mmol), catalyst 4e (0.42 mg, 0.001 mmol) in xylene (0.5 mL) was stirred at room temperature for 7 h. After the solvent was evaporated under vacuum, the residue was purified by flash column chromatography over silica gel (petroleum ether/EtOAc = 3:1) to afford 3a as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With C31H53N3O2S; In toluene; at -30℃; for 2h; | General procedure: The α-phenyl cyanoacetate 2 (0.10 mmol) was added to a mixture of catalyst 1a (10 mol %) and the corresponding maleimide 3 (0.12 mmol) in toluene (1.0 mL). The reaction mixture was stirred at -30 C for the required time. After the α-phenyl cyanoacetate was consumed as determined by TLC analysis, the reaction mixture was subjected to thin layer chromatography on silica gel (ethyl acetate/petroleum ether) to afford the pure Michael product. |
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