Structure of 2039-85-2
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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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CAS No. : | 2039-85-2 |
Formula : | C8H7Cl |
M.W : | 138.59 |
SMILES Code : | C=CC1=CC(Cl)=CC=C1 |
MDL No. : | MFCD00000598 |
InChI Key : | BOVQCIDBZXNFEJ-UHFFFAOYSA-N |
Pubchem ID : | 14905 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 41.54 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.27 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.09 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.87 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.44 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.27 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.99 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.07 |
Solubility | 0.117 mg/ml ; 0.000845 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.76 |
Solubility | 0.242 mg/ml ; 0.00175 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.43 |
Solubility | 0.0515 mg/ml ; 0.000372 mol/l |
Class? Solubility class: Log S scale |
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) |
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 |
-4.95 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 |
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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.38 |
* 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 tributyl-amine; citric acid;palladium diacetate; In N,N-dimethyl acetamide; ethyl acetate; | Example 127 0.076 mL of 3-chlorostyrene, 0.19 mL of tributylamine, 2.9 mg of tri-tert-butylphosphine tetrafluoroborate and 4.5 mg of palladium acetate were added to 2.0 mL of N,N-dimethylacetamide solution containing 0.15 g of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature and stirred under nitrogen atmosphere at 110°C for 4 hours and 30 minutes. After the reaction mixture was cooled to room temperature, 0.025 mL of 3-chlorostyrene, 2.9 mg of tri-tert-butylphosphine tetrafluoroborate and 4.5 mg of palladium acetate were added at room temperature and stirred under nitrogen atmosphere at 110°C for 1 hour and 20 minutes. After the reaction mixture was cooled to room temperature, 10percent citric acid aqueous solution and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10percent citric acid aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 10:1] to obtain 86 mg of tert-butyl 2-(benzamido)-4-((E)-2-(3-chlorophenyl)vinyl)benzoate as white solid. 1H-NMR (CDCl3) delta: 1.56 (9H, s), 7.13=7.34 (5H, m), 7.40-7.45 (1H, m), 7.52-7.59 (4H, m), 8.01 (1H, d, J = 8.3 Hz), 8.06-8.11 (2H, m), 9.16 (1H, d, J = 1.7 Hz), 12.27 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73%Chromat. | With tert.-butylhydroperoxide; oxygen; potassium carbonate; at 150℃; under 7500.75 Torr; for 48h;Autoclave; Green chemistry; | General procedure: In the typical oxidation reaction, the substrate (0.25 mmol), catalyst(10 mol%), K2CO3 (20 mol%), TBHP (2.2 equiv.) and MeOH (4 mL) wereplaced in a round-bottomed flask. The mixture was then transferred tothe autoclave. The autoclave was closed and purged with oxygen for 3times. Finally, the autoclave was pressurized in oxygen atmosphere for48 h and stirred at 150 C. After the reaction was completed, the autoclavewas cooled to room temperature, the internal standard compound(biphenyl, 15 mg) and MeOH (2 mL) were added. The reaction solutionwas analyzed on GC and confirmed by GC-MS. Or the yield was determinedby 1HNMR using dibromomethane (10 mg) as the internalstandard. |