Structure of 7417-18-7
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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. : | 7417-18-7 |
Formula : | C9H12O2 |
M.W : | 152.19 |
SMILES Code : | COC1=CC=CC=C1CCO |
MDL No. : | MFCD00002889 |
Boiling Point : | No data available |
InChI Key : | XLDRDNQLEMMNNH-UHFFFAOYSA-N |
Pubchem ID : | 81909 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 43.87 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.03 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.96 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.23 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.53 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.0 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.75 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.22 |
Solubility | 0.909 mg/ml ; 0.00597 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.2 |
Solubility | 0.952 mg/ml ; 0.00626 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.74 |
Solubility | 0.276 mg/ml ; 0.00181 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 |
-5.84 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) |
1.15 |
* 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 |
---|---|---|
82% | With caesium carbonate; In acetone; at 0℃; for 0.833333h;Inert atmosphere; | Step A: To a stirred suspension of 2-(2-hydroxyethyl)phenol (5 g, 36.2 mmol) and CS2CO3 (38.9 g, 108.7 mmol) in acetone (100 mL) was added iodomethane (6.2 g, 43.4 mmol) in an ice bath. The reaction mixture was stirred at 0 °C for 50 minutes. The mixture was filtered, the filtrate was concentrated under vacuum. The crude materials was extracted with EtOAc and water. The organic layer was dried over anhydrous Na2S04 and concentrated to afford 2-(2-methoxyphenyl)ethanol (4.5 g, 29.6 mmol, 82percent yield) as a yellow solid. |
82% | With caesium carbonate; In acetone; at 0℃; for 0.833333h; | To a stirred suspension of 2-(2-hydroxyethyl)phenol (5 g, 36.2 mmol) and Cs2C03 (38.9 g, 108.7 mmol) in acetone (100 mL) was added iodomethane (6.2 g, 43.4 mmol) in an ice bath. The reaction mixture was stirred at 0 °C for 50 minutes. The mixture was filtered, the filtrate was concentrated under vacuum. The crude materials were extracted with EtOAc and water. The organic layer was dried over anhydrous Na2S04 and concentrated to afford 2-(2-methoxyphenyl)ethanol (4.5 g, 29.6 mmol, 82percent yield) as a yellow solid. |
With caesium carbonate; In acetone; at 20℃; for 0.833333h; | To a solution of 10 g of 2- (2-HYDROXYPHENYL)-ETHANOL in 200 ml of acetone there are added 35.3 g of Cs2CO3 and then a solution of 6.5 ml of methyl iodide in 40 ml of acetone. The reaction mixture is stirred for 50 minutes at room temperature, is filtered and is concentrated by evaporation. The residue is partitioned between diethyl ether and water. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation, and the residue is purified by means of FC (dichloromethane/diethyl ether=97: 3), yielding the title compound: Rf (DICHLOROMETHANE/DIETHYL ether=97: 3) =0.34 ; HPLC Rt =9.31 minutes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone; | a) 2-(2-Hydroxyethyl)-anisole To a solution of 10 g of 2-(2-hydroxyphenyl)-ethanol in 200 ml of acetone there are added 35.3 g of Cs2 CO3 and then a solution of 6.5 ml of methyl iodide in 40 ml of acetone. The reaction mixture is stirred for 50 minutes at room temperature, is filtered and is concentrated by evaporation. The residue is partitioned between diethyl ether and water. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation, and the residue is purified by means of FC (dichloromethane/diethyl ether=97:3), yielding the title compound: Rf (dichloromethane/diethyl ether=97:3)=0.34; HPLC Rt =9.31 minutes. |
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