Structure of 772-38-3
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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. : | 772-38-3 |
Formula : | C12H14 |
M.W : | 158.24 |
SMILES Code : | C#CC1=CC=C(C(C)(C)C)C=C1 |
MDL No. : | MFCD00190197 |
InChI Key : | ZSYQVVKVKBVHIL-UHFFFAOYSA-N |
Pubchem ID : | 2757302 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H319-H372-H410 |
Precautionary Statements: | P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 |
Class: | 9 |
UN#: | 3082 |
Packing Group: | Ⅲ |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 53.65 |
TPSA ? Topological Polar Surface Area: Calculated from |
0.0 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.82 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
5.05 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.05 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.96 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.67 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.91 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.31 |
Solubility | 0.00781 mg/ml ; 0.0000494 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.79 |
Solubility | 0.00256 mg/ml ; 0.0000162 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.68 |
Solubility | 0.0333 mg/ml ; 0.00021 mol/l |
Class? Solubility class: Log S scale |
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 |
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) |
Yes |
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 |
-3.68 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
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 |
3.0 |
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) |
1.7 |
* 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 |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 6.0h;Inert atmosphere; | <strong>[197007-87-7](4-bromopyridin-3-yl)methanol</strong> (0.84 g, 5.32 mmol), 4-tert-Butylphenyl acetylene (1.0 g, 5.32 mmol), triethylamine (2.5 mL, 17.9 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.19 g, 0.27 mmol), copper(I) iodide (0.06 g, 0.29 mmol), N,N-dimethylformamide (15 mL) Under a nitrogen atmosphere, the mixture was stirred for 6 hours at 80C. Was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate to the reaction solution. The organic layer was washed with saturated brine, and dried with anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the solvent was evaporated under reduced pressure. Flash chromatograph the residueIt over was purified (eluent n- heptane / ethyl acetate) to obtain the desired product (1.73 g, purity 69%, 85% yield). | |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 6.0h;Inert atmosphere; | <strong>[197007-87-7](4-bromopyridin-3-yl)methanol</strong> (0.84 g, 5.32 mmol), 4-tert-butylphenylacetylene (1.0 g, 5.32 mmol), triethylamine (2.5 mL, 17.9 mmol), bis (triphenylphosphine) palladium (II) dichloride (0.19 g, 0.27 mmol), copper iodide (I) (0.06 g, 0.29 mmol), N, N- dimethylformamide (15 mL) under a nitrogen atmosphere and stirred for 6 hours at 80 C.. Was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate to the reaction solution. The organic layer was washed with saturated brine, and dried with anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography purification (eluent n- heptane / ethyl acetate) to obtain the desired product (1.73 g, purity 69%, 85% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With copper(I) bromide; In toluene; at 100℃; for 4h;Inert atmosphere; Sealed tube; | General procedure: To a vial equipped with a magnetic stir bar were added amine (1.5mmol, 14a-e), aldehyde (1.0mmol, 15), acetylene (3.0mmol, 16a-j), copper bromide (0.36mmol, 25mol%) and toluene (1.0mL). The reaction mixture was degassed and backfilled with argon. Then, reaction vessel was sealed and heated conventionally at 100C for 4h. The resulting reaction mixture was cooled to ambient temperature, diluted with dichloromethane (2mL) and purified by column chromatography with 10-15% EtOAc in heptane to afford the desired product ( 17a-x). |