Structure of 129946-88-9
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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. : | 129946-88-9 |
Formula : | C14H8F6O3S2 |
M.W : | 402.33 |
SMILES Code : | [O-]S(=O)(=O)C(F)(F)F.FC(F)(F)[S+]1C2=CC=CC=C2C2=CC=CC=C12 |
MDL No. : | MFCD00236132 |
InChI Key : | QXXHXTRTGZBOGD-UHFFFAOYSA-M |
Pubchem ID : | 2777507 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 25 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 9.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 77.63 |
TPSA ? Topological Polar Surface Area: Calculated from |
90.88 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
5.83 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
7.88 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.28 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
4.18 |
Log S (ESOL):? ESOL: Topological method implemented from |
-6.23 |
Solubility | 0.000237 mg/ml ; 0.000000588 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (Ali)? Ali: Topological method implemented from |
-7.51 |
Solubility | 0.0000124 mg/ml ; 0.0000000309 mol/l |
Class? Solubility class: Log S scale |
Poorly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-5.91 |
Solubility | 0.000493 mg/ml ; 0.00000122 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
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) |
Yes |
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 |
-4.61 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 |
1.0 |
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 |
3.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.2 |
* 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 |
---|---|---|
93% | With copper; In N,N-dimethyl-formamide; at 0 - 80℃; for 4h;Inert atmosphere; | Under the protection of N2,To a 100 ml three-necked flask was added <strong>[10386-27-3]2-bromo-4-cyanopyridine</strong> (1.83 g, 0.01 mol).25 ml of DMF, Cu powder (1.92 g, 0.03 mol), stirred, and cooled to 0-5 ° C in an ice water bath. add Umemoto reagent (8.76g, 0.02mol).After stirring for 1 hour in an ice water bath,The temperature was further raised to 80 ° C and the reaction was carried out for 3 h. The reaction solution was taken for 19F NMR analysis.With OTf as internal standard, the yield is 93percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of <strong>[174543-74-9]1-benzyl 3-methyl piperidine-1,3-dicarboxylate</strong> (2.0 g, 7.14 mmol) in THF (60 mL) was added LDA (2.0 M in THF) (10.8 mL, 21.66 mmol) dropwise at -78 C. After the solution was stirred for 30 mm at -78 C, S-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate (4.35 g, 10.81 mmol) was added. After addition, the resulting solution was allowed to react, with stirring, for an additional 2 h at -40 C. The reaction was then quenched by the addition of 30 mL of a saturated aqueous solution of NH4C1. The resulting mixture was extracted with EtOAc (3 x 70 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. Purification by silica gel chromatography (eluting with 1:4 EtOAc/pet. ether) afforded 1-benzyl 3-methyl 3-(trifluoromethyl)piperidine-1,3- dicarboxylate as a yellow oil. MS: (ESI, m/z): 346 [M+H]. |
A100642 [131880-16-5]
5-(Trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium tetrafluoroborate
Reason: Different form
A1233408 [129946-87-8]
5-(Trifluoromethyl)dibenzothiophen-5-ium
Reason: Free-salt