Structure of 13807-91-5
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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. : | 13807-91-5 |
Formula : | C10H14O2 |
M.W : | 166.22 |
SMILES Code : | CC(O)COCC1=CC=CC=C1 |
MDL No. : | MFCD00085681 |
InChI Key : | KJBPYIUAQLPHJG-UHFFFAOYSA-N |
Pubchem ID : | 295955 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 48.08 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.35 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.54 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.43 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.56 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.06 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.79 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.95 |
Solubility | 1.88 mg/ml ; 0.0113 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.77 |
Solubility | 2.84 mg/ml ; 0.0171 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.8 |
Solubility | 0.263 mg/ml ; 0.00158 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) |
No |
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 |
-6.22 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) |
2.04 |
* 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 |
---|---|---|
In pyridine; toluene; | A mixture of this (S)-1-benzyloxy-2-hydroxypropane (60 g, 0.36 mol) with anhydrous pyridine (300 g) was cooled with ice, followed by dropwise adding a solution of p-toluenesulfonyl chloride (75.8 g, 0.20 mol) in pyridine (70 ml) at 0 C., agitating the mixture at room temperature for 3 hours, adding toluene (800 ml), agitating the mixture, several times washing the resulting organic layer with water, drying it over anhydrous magnesium sulfate and distilling off toluene to obtain (S)-1-benzyloxy-2-(p-toluenesulfonyloxy)propane (115.2 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53 g | With N-ethyl-N,N-diisopropylamine; In toluene; at 0 - 20℃; for 1h; | The starting compound (S) - 1 - (benzyloxy) propan-2-ol (36g, 217mmol) and diisopropyl ethylamine (39.2g, 303mmol) dissolved in toluene (540 ml) in. In 0 C add a sulfonyl chloride (2.32 ml, 29 . 8mmol), then stirring 2 hours, then the stirring at room temperature 1 hour. After the completion of reaction, water (500 ml) to and toluene (200 ml, two) extraction. First organic layer and ammonium chloride aqueous solution (200 ml) and saturated aqueous sodium chloride solution (200 ml) washing and extraction. Organic layer is dried with anhydrous sodium sulfate, filtered and concentrated. Residue after drying. Generating title compound (53g). |
53 g | With N-ethyl-N,N-diisopropylamine; In toluene; at 0 - 20℃; for 3h; | Starting compound (S)-1-(benzyloxy)propan-2-ol (36 g, 217 mmol) and diisopropylethylamine (39.2 g, 303 mmol) were dissolved in toluene (540 mL). methane sulfonyl chloride (2.32 ml, 29.8 mmol) was added at 0 C., followed by stirring for 2 hr and stirring more at room temperature for 1 hr. After reaction was finished, extraction was performed with water (500 ml) and toluene (200 ml, twice). The organic layer was extracted by saturated ammonium chloride aqueous solution (200 ml) and saturated sodium chloride aqueous solution (200 ml), and washed. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was dried. The title compound (53 g) was produced. 1H-NMR (CDCl3, Varian 400 MHz): delta 1.40 (3H, d, J=6.4 Hz), 3.01 (3H, s), 3.52-3.61 (2H, m), 4.55 & 4.57 (2H, ABq, JAB=11.8 Hz), 4.88-4.96 (1H, m), 7.26-7.38 (5H, m). |
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