Structure of 873-63-2
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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. : | 873-63-2 |
Formula : | C7H7ClO |
M.W : | 142.58 |
SMILES Code : | ClC1=CC(CO)=CC=C1 |
MDL No. : | MFCD00004632 |
Boiling Point : | No data available |
InChI Key : | ZSRDNPVYGSFUMD-UHFFFAOYSA-N |
Pubchem ID : | 70117 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335-H412 |
Precautionary Statements: | P261-P273-P305+P351+P338 |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 37.58 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.93 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.94 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.68 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.14 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.33 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.0 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.37 |
Solubility | 0.603 mg/ml ; 0.00423 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.99 |
Solubility | 1.46 mg/ml ; 0.0103 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.82 |
Solubility | 0.217 mg/ml ; 0.00152 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 |
-5.79 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) |
1.0 |
* 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 lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 1h;Inert atmosphere; | General procedure: To a solution of methyl phenyl acetates (1.0 eq.) in dry THF (5mL) was added LiAlH4 (2 eq.) at 0C under N2 atmosphere, and the resulting mixture was stirred at room temperature for 1h [23]. After complete consumption of starting material, the reaction mixture was quenched with Na+/K+ tartrate solution (∼10mL), and the mixture was filtered after being stirred at room temperature overnight. The collected filtrate was dried and concentrated to afford crude alcohol intermediate, which was oxidized by PCC (2 eq.) for 2h in CH2Cl2 (5-10mL) [24,25]. The reaction mixture was filtered through short silica column to remove brown side-product. The collected filtrate was concentrated in vacuo for next step without any purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With carbon tetrabromide; oxygen; at 20℃; for 20h;Irradiation; | General procedure: Typical procedure: A solution of 4-tert-butylbenzyl alcohol (1a, 0.3 mmol) and CBr4 (0.09 mmol) in dry MeOH (4 mL) in a pyrex test tube, purged with an O2-balloon, was stirred and irradiated externally with four 22 W fluorescent lamps for 20 h. The reaction mixture was concentrated in vacuo. Purification of the crude product by PTLC (toluene) provided methyl 4-tert-butylbenzoate (2a) (Rf = 0.40, 54.0 mg, 94%). |
90% | With Au#Co; oxygen; potassium carbonate; at 80℃; under 750.075 Torr; for 10h;Autoclave; | 20 mg of Au-Co composite particle support (0.1 mol%), 13.8 mg of K2CO3 (10 mol%), 142.5 mg of m-chlorobenzyl alcohol (1 mmol),4 mL of methanol was sequentially added to a pressure vessel with a 25 mL glass lining. After replacing the oxygen three times, the pressure was increased to 0.1 MPa, and the reaction was carried out at 80 C for 10 hours. After cooling to room temperature, the gas was slowly depressurized, the catalyst was filtered, and the filtrate was concentrated by steaming. After residue column chromatographyYellowish liquid productMethyl m-chlorobenzoate 164.7mg,The yield was 90%. |
86% | With 1H-imidazole; tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In water; at 80℃; for 7h;Green chemistry; | General procedure: To a mixture of benzyl alcohol (108 mg, 1.0 mmol) and TBHP(180 mg, 2.0 mmol) in water (3 ml), the catalyst TBAI (73.8 mg,0.2 mmol), imidazole (136 mg, 2.0 mmol), and MeOH (2 ml)were added, and the mixture was stirred at 80 C for 8 h. Theprogress of the reaction was monitored by TLC. After completionof reaction, the reaction mixture was cooled to room temperature.Then MeOH was distilled out, and the organic productwas extracted with ethyl acetate (3 × 10 ml), repeatedly washedwith distilled water (4 × 5 ml) to remove the unreacted TBHP,dried with anhydrous sodium sulfate, and the solvent was evaporatedunder reduced pressure to afford methyl benzoate (112mg, yield 82%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With C20H16Cl2N2Pd; potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 6h; | General procedure: A 50 mL round bottom flask was charged with a mixture of aryl chloride (0.5 mmol), arylboronic acid (0.75 mmol), K2CO3 (1.5 mmol), Pd catalyst (0.2 mol %), solvent (6 mL) and the mixture was stirred for required times at appropriate temperature. After completion, the reaction mixture was diluted with water (20 mL) and extracted with ether (20 mL ×3). Combined extract was washed with brine (20 mL ×3) and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel, ethyl acetate/hexane 1:9) to obtain the desired product. The products were confirmed by comparing the melting points, 1H NMR and mass spectral data with authentic samples. |
60% | With 2Na(1+)*C26H18N2O8PdS2(2-); cetyltrimethylammonim bromide; potassium carbonate; In water; at 100℃; for 8h; | General procedure: The Suzuki reaction was performed in a 50 mL round-bottomed flask, aryl halide (0.5 mmol), arylboronic acid (0.65 mmol), K2CO3 (1 mmol), Complex 1 (0.2-1 mol%) and water (4 mL) were charged and stirred for the required time at room temperature for aryl bromides or at 100 C for aryl chlorides. After completion, the mixture was cooled down to room temperature, diluted with water (10 mL) and extracted with diethyl ether (3 × 15 mL). The organic layer was washed with brine (3 × 15 mL), dried over anhydrous Na2SO4. The crude products were chromatographed on silica gel (ethyl acetate/hexane). |
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