Structure of 711-33-1
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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. : | 711-33-1 |
Formula : | C10H9F3O |
M.W : | 202.17 |
SMILES Code : | CCC(C1=CC=C(C(F)(F)F)C=C1)=O |
MDL No. : | MFCD00039231 |
InChI Key : | QFKOWENRSZZLPK-UHFFFAOYSA-N |
Pubchem ID : | 136554 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.3 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 46.45 |
TPSA ? Topological Polar Surface Area: Calculated from |
17.07 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.18 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.07 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.45 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.1 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.54 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.27 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.15 |
Solubility | 0.144 mg/ml ; 0.000713 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.1 |
Solubility | 0.162 mg/ml ; 0.000803 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.03 |
Solubility | 0.0189 mg/ml ; 0.0000933 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
-5.35 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) |
1.22 |
* 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 |
---|---|---|
1.58 g (44.8%) | With paraformaldehyde; In isopropyl alcohol; | 1-(4-Trifluoromethylphenyl)-2-methyl-3-pyrrolidino-1-propanone hydrochloride To a mixture of 2.50 g of 1-(4-trifluoromethylphenyl)-1-propanone, 1.11 g of paraformaldehyde, 1.60 g of <strong>[25150-61-2]pyrrolidine hydrochloride</strong> and 20 ml of isopropanol was added 0.1 ml of concentrated hydrochloride acid, and the resulting solution was heated under reflux for 16 hours. After completion of the reaction, the reaction solution was evaporated under reduced pressure to give the residue. To the resulting residue was added with water and washed with ethyl acetate. The aqueous layer was alkalized with aqeous ammonia, and then was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium salfate, and then was evaporated under reduced pressure to give 1.58 g (44.8%) of 1-(4-trifluoromethylphenyl)-2-methyl-3-pyrrolidino-1-propanone as an oil. Mass m/z (relative intensity): 285 (2.21, M+), 214 (100), 173 (100), 145 (100), 95 (29.7), 84 (100) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.58 g (44.8%) | With paraformaldehyde; In isopropyl alcohol; | 1-(4-Trifluoromethylphenyl)-2-methyl-3-pyrrolidino-1-propanone hydrochloride To a mixture of 2.50 g of 1-(4-trifluoromethylphenyl)-1-propanone, 1.11 g of paraformaldehyde, 1.60 g of <strong>[25150-61-2]pyrrolidine hydrochloride</strong> and 20 ml of isopropanol was added 0.1 ml of concentrated hydrochloride acid, and the resulting solution was heated under reflux for 16 hours. After completion of the reaction, the reaction solution was evaporated under reduced pressure to give the residue. To the resulting residue was added with water and washed with ethyl acetate. The aqueous layer was alkalized with aqeous ammonia, and then was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sa lfate, and then was evaporated under reduced pressure to give 1.58 g (44.8%) of 1-(4-trifluoromethylphenyl)-2-methyl-3-pyrrolidino-1-propanone as an oil. This oil was dissolved in ethyl ether and gaseous hydrogen chloride introduced into the solution to give the corresponding hydrochloride salt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; paraformaldehyde; | EXAMPLE 2 1-(4-Trifluoromethylphenyl)-2-methyl-3-pyrrolidino-1-propanone (Compd. No. 4-1) hydrochloride. A mixture of 1-(4-trifluoromethylphenyl)-1-propanone (2.50g), paraformaldehyde (1.10g), <strong>[25150-61-2]pyrrolidine hydrochloride</strong> (1.60g), and hydrochloric acid (0.1 ml) was refluxed for 16 hours. The mixture was evaporated in vacuo to give the residue. The residue was partitioned into water and ethyl acetate. The aqueous layer was neutralized with ammonia water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was evaporated in vaccuo to give 1-(4-trifluoromethylphenyl)-2-methyl-3-pyrrolidino-1propanone (1.58g; yield: 44.8%) as an oil. IR νmaxneat: 1690 cm-1 STR321 Mass m/z (relative intensity): 285 (2.21, M+), 214 (100); 173 (100), 145 (100), 95 (29.7), 84 (100). |
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