Structure of 106263-50-7
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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. : | 106263-50-7 |
Formula : | C10H9ClO3 |
M.W : | 212.63 |
SMILES Code : | OC(=O)CCC(=O)C1=C(Cl)C=CC=C1 |
MDL No. : | MFCD03844205 |
Boiling Point : | No data available |
InChI Key : | JIFTXSSZTRPMNW-UHFFFAOYSA-N |
Pubchem ID : | 20274428 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.2 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 53.03 |
TPSA ? Topological Polar Surface Area: Calculated from |
54.37 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.53 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.52 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.39 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.88 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.44 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.95 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.17 |
Solubility | 1.44 mg/ml ; 0.00678 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.27 |
Solubility | 1.14 mg/ml ; 0.00537 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.15 |
Solubility | 0.15 mg/ml ; 0.000705 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 |
-6.52 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 |
0.56 |
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) |
1.51 |
* 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 |
---|---|---|
99% | With sulfuric acid; for 144.0h;Reflux; | 50 g (235 mmol) of <strong>[106263-50-7]4-chlorophenyl-4-oxobutanoic acid</strong> were solubilized in 300 ml of isopropanol, 0.63 ml (11.76 mmol) of sulfuric acid were added to this solution. The mixture was refluxed with heating for 6 d with magnetic stirring. After returning to r.t., the mixture was concentrated in vacuo, the crude residue was directly purified by flash chromatography on a silica gel cartridge (eluent: 100% dichloromethane). 59.83 g (yield=>99%) of isopropyl 4-chlorophenyl-4-oxobutanoate were obtained as a colorless oil. LC-MS: m/z=255 (MH+) UV purity at 254 nm=95%. 1H NMR (300 MHz, DMSO) δ 8.13-7.85 (m, 2H), 7.70-7.47 (m, 2H), 4.86 (dt, J=12.5, 6.3 Hz, 1H), 3.29-3.22 (m, 2H), 2.65-2.54 (m, 2H), 1.16 (d, J=6.3 Hz, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With bromobenzene; magnesium; In tetrahydrofuran; at -40 - 0℃; for 1.5h; | General procedure: At -40 C, glutaric anhydride (B) (60mmol) / anhydrous THF (125mL)Slowly add 2chlorophenylmagnesium bromide (A ') / THF (50mL) to the solutionMagnesium filings (55 mmol) and bromobenzene (45 mmol) were generated in situ in the solution. after finishing,At the same temperature, the reaction mixture was continuously stirred for 1.5 hours,It was then cooled with 1N hydrochloric acid (250 mL). The mixture was extracted with ethyl acetate (250 mL3), and the extract was dried over anhydrous MgSO4,Concentrated in vacuo to give crude 5- (2-chlorophenyl) -5-oxovaleric acid (1'a),It was recrystallized from petroleum ether and ethyl acetate with a yield of 32%. |
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