Structure of 1131912-76-9
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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. : | 1131912-76-9 |
Formula : | C11H21BO3 |
M.W : | 212.09 |
SMILES Code : | CC1(C)OB(OC1(C)C)C1CCOCC1 |
MDL No. : | MFCD11506065 |
InChI Key : | NLSMOSUUBUCSPL-UHFFFAOYSA-N |
Pubchem ID : | 42614649 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 60.9 |
TPSA ? Topological Polar Surface Area: Calculated from |
27.69 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 |
1.84 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.26 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.93 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.34 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.27 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.25 |
Solubility | 1.2 mg/ml ; 0.00565 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.04 |
Solubility | 1.93 mg/ml ; 0.00908 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.38 |
Solubility | 0.876 mg/ml ; 0.00413 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) |
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 |
-6.29 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
3.14 |
* 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 |
---|---|---|
32% | With triethylamine; for 1h; | General procedure: General Procedure B: NHPI ester (1.0 eq., 0.13 mmol) and B2cat2 (40 mg, 1.25 eq., 0.16 mmol) were carefully weighed into a flame-dried 7 mL vial containing a small magnetic stiffer bar. DMAc (1.3 mL, 0.1 M) was added and then the headspace of thevial was purged with a gentle stream of argon for approximately 10 seconds. The vial was tightly sealed and stirred under blue LED iffadiation for 14 h. Pinacol (63 mg, 0.53 mmol, 4 eq.) was dissolved in Et3N (0.45 mL), added to the reaction mixture and stuffed for 1 h. For workup, the reaction mixture was transfeffed into a vial containing EtOAc (15 mL), H20 (3 mL), NH4Cl (saturated aqueous solution, 3 mL). After vigorouslyshaking and allowing the two layers to separate, the top organic layer was carefully removed with a pipette. This was repeated twice more with EtOAc delta mL). The organic layers were combined and concentrated under reduced pressure. The crude residue was directly purified using a short silica gel column to yield the desired boronic ester. Alternative workup: The crude reaction mixture was diluted with Et20 (10 mL) andwashed with NaOH (aqueous, 0.10 M, 6 mL), and then the aqueous layer was extracted with Et20 (10 mL). The combined organic layers were washed with NaOH (aqueous,0.10 M, 6 mL) and water (6 mL), then dried over MgSO4, filtered and concentrated under reduced pressure to yield the desired boronic ester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With lithium tert-butoxide; In methanol; water; at 50℃; for 48h;Glovebox; | IN a glove box, t-BuOLi (1 mmol, 2 equivalents, 80.1 mg), B2pin2 (2 mmol, 4 equivalents, 507.9 mg), 0.85 mL of solvent methanol, 10 muL of H 2 O were added to the vial containing the stirrer in turn.4-iodotetrahydropyran (0.5 mmol). The capped vial was removed from the glove box and the reaction mixture was stirred at 50 C for 48 hours. After cooling to room temperature, the reaction mixture was transferred to a 100 mL flask by methanol, and then a small amount of silica gel was added thereto. After removing the solvent in a vacuum, the residue was poured onto a silica gel column and purified by column chromatography, and the solvent was a mixture of petroleum ether/ethyl acetate in a volume ratio of 30:1 to 20:1.The desired product, 4-tetrahydropyranylboronic acid pinacol ester, was obtained in a yield of 50%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium phosphate; palladium on activated charcoal; In 1,4-dioxane; water; at 80℃; for 4h;Inert atmosphere; | Interventional 2-bromo-N-(cyclopropylmethyl)-5-nitrobenzamide 50 mg (1 eq) into a 50 mL vial.Tetrahydrofuran-3-boronic acid pinacol ester 52mg (1eq),PdXPhosG2 1mg (0.01eq), Pd/C 22mg (0.12eq),Potassium phosphate 107mg (3eq), then sealed with argon to replace the air in the single-mouth bottle three times, to ensure no oxygen, then add 1-4, dioxane: water = 4:1 (5mL),After the addition was completed, the gas in the three-necked flask was replaced with argon gas, and then the temperature was raised to 80 C, and after reacting for 4 hours,The heating device was turned off, the reaction was allowed to cool to room temperature, and then 106 mg (10 eq) of ammonium formate was dissolved in 2 mL of methanol.After completely dissolved, it is added to the reaction system and reacted at room temperature for 16 hours.The reaction was completely detected by TLC, and then filtered through celite, and the filtrate was concentrated under reduced pressure, and then directly separated by column chromatography.47 mg of a white solid were obtained in a yield of 75%. |
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