Structure of 183158-34-1
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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. : | 183158-34-1 |
Formula : | C8H11BO2 |
M.W : | 149.98 |
SMILES Code : | OB(C1=CC=CC(C)=C1C)O |
MDL No. : | MFCD01863524 |
InChI Key : | ZYYANAWVBDFAHY-UHFFFAOYSA-N |
Pubchem ID : | 2773395 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 46.2 |
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 |
1.56 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
-0.02 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.94 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.15 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.53 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.09 |
Solubility | 1.22 mg/ml ; 0.00812 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.02 |
Solubility | 1.43 mg/ml ; 0.00956 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.04 |
Solubility | 1.36 mg/ml ; 0.00904 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 |
No |
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 |
-6.11 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) |
1.47 |
* 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 |
---|---|---|
30% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 6.0h;Reflux; | Step 2: 2-Cyano-2',3'-dimethyl-biphenyl-4-olA mixture of <strong>[189680-06-6]4-bromo-3-cyanophenol</strong> (1.0 g, 5 mmol), 2,3-dimethylphenylboronic acid (1.1 g, 8 mmol), tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.43 mmol) and a 2M sodium carbonate solution (5 ml ) in 50 ml of 1 ,2-dimethoxyethane was heated at reflux for 6 hours. The mixture was cooled and was poured into an aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and filtered. The concentrated filtrate was purified by flash chromatography on silica gel using 0-10% ethyl acetate/heptane to provide the title compound, 133-7C, mp (0.33 g, 30%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 6.0h;Reflux; | Step 2: 2-Ethyl-2',3'-dimethyl-biphenyl-4-olA mixture of <strong>[99873-30-0]4-bromo-3-ethylphenol</strong> (1.6 g, 7.96 mmol), 2,3-dimethylphenylboronic acid (1.2 g, 7.96 mmol), tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.86 mmol) and a 2M sodium carbonate solution (6 ml) in 1 ,2-dimethoxyethane(70 ml) was heated at reflux for 6 hours. The mixture was cooled and was poured into an aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (150 ml). The organic layer was washed with water, dried over magnesium sulfate and filtered. The concentrated filtrate was purified by flash chromatography on silica gel using 100% heptane, then 9: 1 heptane:ethyl acetate to provide the title compound (0.7 g, 39%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With dichlorobis(triphenylphosphine)palladium[II]; In 1,2-dimethoxyethane; | (1) Synthesis of 4-(2,3-dimethylphenyl)indene 38 g (180 mmol) of tripotassium phosphate, 100 mL of distilled water, 100 mL of DME, 10 g (66.7 mmol) of 2,3-dimethylphenylboronic acid, 10.8 g (55.4 mmol) of <strong>[16657-07-1]7-bromo-1H-indene</strong>, 1.0 g (1.42 mmol) of dichlorobis(triphenylphosphine)palladium, and 1.30 g (4.96 mmol) of triphenyl phosphine were put into a 500-mL glass reactor in that order, and then heated under reflux at 90 C. for 11 hours. This was left cooled to room temperature, and the reaction liquid was poured into 100 mL of distilled water, transferred into a separatory funnel, and extracted three times with hexane. 6 mL of concentrated hydrochloric acid was added to the hexane solution at room temperature, then stirred at room temperature for 30 minutes, the palladium compound was precipitated, filtered away through filter paper, and the filtrate was washed three times each with saturated saline water and distilled water, and then dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent, hexane/diisopropyl ether=20/1) to give 11.66 g (yield 96%) of 4-(2,3-dimethylphenyl)indene as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; at 90℃; for 11h; | 38 g (180 mmol) of tripotassium phosphate, 100 mL of distilled water, 100 mL of DME, 10 g (66.7 mmol) of 2,3-dimethylphenylboronic acid, 10.8 g (55.4 mmol) of <strong>[16657-07-1]7-bromo-1H-indene</strong>, 1.0 g (1.42 mmol) of dichlorobis(triphenylphosphine)palladium, and 1.30 g (4.96 mmol) of triphenyl phosphine were put into a 500-mL glass reactor in that order, and then heated under reflux at 90 C. for 11 hours. This was left cooled to room temperature, and the reaction liquid was poured into 100 mL of distilled water, transferred into a separatory funnel, and extracted three times with hexane. 6 mL of concentrated hydrochloric acid was added to the hexane solution at room temperature, then stirred at room temperature for 30 minutes, the palladium compound was precipitated, filtered away through filter paper, and the filtrate was washed three times each with saturated saline water and distilled water, and then dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent, hexane/diisopropyl ether=20/1) to give 11.66 g (yield 96%) of 4-(2,3-dimethylphenyl)indene as a colorless oil. |