Structure of 5527-95-7
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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. : | 5527-95-7 |
Formula : | C7H4ClFO |
M.W : | 158.56 |
SMILES Code : | C1=C(C=CC(=C1F)Cl)C=O |
MDL No. : | MFCD00143288 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 36.8 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.56 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.11 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.71 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.48 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.04 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.38 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.53 |
Solubility | 0.468 mg/ml ; 0.00295 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.1 |
Solubility | 1.26 mg/ml ; 0.00796 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.23 |
Solubility | 0.0938 mg/ml ; 0.000592 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 |
-5.77 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 |
1.0 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) |
1.16 |
* 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 |
---|---|---|
toluene-4-sulfonic acid; In toluene; for 2h;Heating / reflux; | 3.2 g (20 mmol) of the aldehyde 18 and 4.7 g (30 mmol) of the 1,3-diol are dissolved in 50 ml of toluene, 0.4 g of p-toluenesulfonic acid is added, and the mixture is heated on a water separator for 2 h. The cooled solution is washed with sat. sodium hydrogencarbonate solution and evaporated. The residue is passed through silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate; In methanol; at 20℃; | General procedure: In the first synthetic step (step a, Scheme 1), a series of (Z)-substituted diarylacrylonitrile analogues were synthesized by reacting substituted benzyl carbaldehydes with their corresponding substituted phenylacetonitriles in 5% NaOMe in methanol. The reaction mixture was stirred at room temperature for 2-3 h for the reaction to complete and the final product precipitated of the solution. The precipitate was filtered, washed with water and dried to yield the final compound in yields ranging from 70 to 95% (Scheme 1) [16]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30.9g | With toluene-4-sulfonic acid; In toluene;Inert atmosphere; Reflux; Dean-Stark; | Under a nitrogen atmosphere, 4-chloro-3-fluorobenzaldehyde (25 g), <strong>[2612-28-4]2-propyl-1,3-propanediol</strong> (18.6 g), and p- toluenesulfonic acid monohydrate (0 the .90g) was dissolved in toluene (500mL), it was brought to reflux.The resulting water was removed using a Dean-Stark apparatus, and stirred for further 30 minutes.Was allowed to cool to room temperature, the addition of a saturated aqueous solution of sodium hydrogen carbonate (200mL) were separated, and the organic layer was washed with saturated brine (200mL), and dried over anhydrous sodium sulfate, evaporated under reduced pressure and the organic solvent did.The residue was purified by silica gel column chromatography, and recrystallized from methanol to give 2- (4-chloro-3-fluoro-phenyl) -5-propyl-1,3-dioxane (30.9g). |
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