Structure of 145240-28-4
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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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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 145240-28-4 |
Formula : | C10H15BO2 |
M.W : | 178.04 |
SMILES Code : | C(CCC)C1=CC=C(C=C1)B(O)O |
MDL No. : | MFCD02093926 |
InChI Key : | UGZUUTHZEATQAM-UHFFFAOYSA-N |
Pubchem ID : | 4100860 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 55.65 |
TPSA ? Topological Polar Surface Area: Calculated from |
40.46 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 |
2.71 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.71 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.56 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.72 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.14 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.73 |
Solubility | 0.333 mg/ml ; 0.00187 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.21 |
Solubility | 0.109 mg/ml ; 0.000612 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.89 |
Solubility | 0.231 mg/ml ; 0.0013 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) |
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 |
-5.46 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 |
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) |
1.65 |
* 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 |
---|---|---|
34% | In N2 (purity of 99.999%) filled glove box (O2 < 0.1ppm, H2O < 0.1 ppm), to an oven-dried screwed 20 mL vial were added Palladium catalyst (5 mol%), Ligand (5 or 10 mol%), Base (2 eq.), Boronic acids 3 (1.5 eq.) and THF (3 mL), then allene 1a (0.2 mmol, 36 mg) and phenyl iodide 2a (1.2 eq., 49 mg) were also charged into the formed suspension above. The joint position between vial and cap was sealed with black electric tape to save the nitrogen in it and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13-15 hours on the IKA electric stirring machine. The reaction process was monitored by TLC (Hexane/Ethyl acetate = 2:1) method to show that the precursor of allyllic alcohol was formed completely. Then, imidazole (8 eq. 108 mg) and TBSCl (3 eq. 90 mg) were added into the vial under air and kept stirring for around 2 hours, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the reaction of producing the protected allyl alcohol by TBS group 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a. The results were summarized in Table 1 as below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26%; 64% | In N2 (purity of 99.999%) filled glove box (O2 < 0.1ppm, H2O < 0.1 ppm), to an oven-dried screwed 20 mL vial were added Palladium catalyst (5 mol%), Ligand (5 or 10 mol%), Base (2 eq.), Boronic acids 3 (1.5 eq.) and THF (3 mL), then allene 1a (0.2 mmol, 36 mg) and phenyl iodide 2a (1.2 eq., 49 mg) were also charged into the formed suspension above. The joint position between vial and cap was sealed with black electric tape to save the nitrogen in it and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13-15 hours on the IKA electric stirring machine. The reaction process was monitored by TLC (Hexane/Ethyl acetate = 2:1) method to show that the precursor of allyllic alcohol was formed completely. Then, imidazole (8 eq. 108 mg) and TBSCl (3 eq. 90 mg) were added into the vial under air and kept stirring for around 2 hours, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the reaction of producing the protected allyl alcohol by TBS group 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a. The results were summarized in Table 1 as below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15%; 80% | In an N2 charged glove box with oxygen and water levels ?0.1 ppm, to an oven-dried screwed vial were added complex 8 (51 mg, 0.05 mmol), K2CO3 (13.8 mg, 0.1 mmol, 2 eq.), boronic acids 3a (9 mg, 0.05mmol, 1 eq.) and THF (3 mL), then phenyl iodide 2a (10 mg, 0.05 mmol, 1 eq.) were also charged into the reaction mixture. The joint position between the vial and cap was sealed with black electric tape to save the nitrogen in the vial and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13 hours on the IKA electric stirring machine. After 15 hours, imidazole (17 mg, 0.25 mmol, 5 eq.) and TBSCl (22 mg, 0.15 mmol, 3 eq.) were added into the vial under air and stirred for another 2 hours at room temperature, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the formation of TBS protected allyl alcohol 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a (7 mg, 80%). The spectrum was same as above. The biphenyl product 4aa is also formed with about 1.6 mg (15% yield). There is no reaction occur without the presence of phenyl iodide, which was confirmed by the analysis of 31P NMR of crude reaction mixture. |