Structure of 13826-27-2
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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. : | 13826-27-2 |
Formula : | C12H8B2O4 |
M.W : | 237.81 |
SMILES Code : | B1(B2OC3=CC=CC=C3O2)OC4=CC=CC=C4O1 |
MDL No. : | MFCD09842343 |
InChI Key : | WYBQOWXCLDXZNR-UHFFFAOYSA-N |
Pubchem ID : | 3488065 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 18 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 66.9 |
TPSA ? Topological Polar Surface Area: Calculated from |
36.92 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 |
3.66 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.98 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.83 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.22 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.25 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.05 |
Solubility | 0.0213 mg/ml ; 0.0000896 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.12 |
Solubility | 0.0179 mg/ml ; 0.0000751 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.95 |
Solubility | 0.0266 mg/ml ; 0.000112 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) |
Yes |
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) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.15 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 |
0.0 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.0 |
* 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 |
---|---|---|
81% | In a glove box under a nitrogen atmosphere, B2cat2 (0.45 mmol, 1.5 equiv, 107.0 mg), AIBN (0.33 mmol, 1.1 equiv, 54.2 mg), 2 mL of solvent N,N-dimethylacetamide, TTMSS (0.33 mmol, 1.1 equiv, 101.8 μL) and bromo-n-octane (0.3 mmol, 52.3 μL). The capped Schlenk bottle was removed from the glove box, and the reaction mixture was stirred at 80 C for 6 hours. After cooling to room temperature, pinacol (141.8 mg, 4.0 equivalents) was added to the reaction flask, 1.0 mL of triethylamine was added, and the mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture was transferred to a 125 mL separatory funnel through 30 mL of ethyl acetate, and then 30 mL of water was added thereto for water washing, and then the aqueous phase was extracted 3 times with 30 mL of ethyl acetate. After washing with 100 mL of saturated saline, the organic phase was dried over anhydrous sodium sulfate and filtered, and then 2.0 mL of TBAF (1 mol / L in THF) was added to remove silicon-containing by-products generated by the reaction. Add a small spoon of 200-300 mesh silica gel, remove the solvent under reduced pressure, adsorb the mixture onto silica gel, and purify by column chromatography. The developing agent used is petroleum ether / ethyl acetate volume ratio 50: 1 30: 1 mixed solution to obtain the desired product pinocyl alcohol n-octyl borate 58.4mg, yield 81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In the dried reaction tube, add B2cat2 (4.0eq., 576mg), nBu4NBF4 (50mol%, 99mg), and add the electrode material to the above reaction tube, seal the reaction system, and replace it with inert gas (Ar) three times. A syringe was used to inject 1-iodooctane (0.6 mmol, 144 mg) and DMF (6 mL) into the above three-port reaction tube, and the reaction was conducted for 12 minutes at 25 C. with a current of 200 mA. After the reaction, pinacol (8.0eq., 567mg) and Et3N (1.5mL) were injected into the reaction system and stirred for 1h. The reaction was terminated, and the reaction solution was quenched with 15 mL of saturated sodium chloride solution, and then extracted with ethyl acetate (15 mL×3) for multiple times. The organic phases were combined, and the solvent was removed on the rotary evaporator. Finally, it is separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:150) to obtain 4,4,5,5-tetramethyl-2-octyl-1,3,2-di Oxaborane (116 mg, isolated yield: 80%), the compound is a colorless liquid. |