Structure of 4187-87-5
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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. : | 4187-87-5 |
Formula : | C9H8O |
M.W : | 132.16 |
SMILES Code : | C#CC(C1=CC=CC=C1)O |
MDL No. : | MFCD00021860 |
InChI Key : | UIGLAZDLBZDVBL-UHFFFAOYSA-N |
Pubchem ID : | 20155 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.11 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 40.35 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.94 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.33 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.11 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.1 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.01 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.7 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.88 |
Solubility | 1.76 mg/ml ; 0.0133 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.36 |
Solubility | 5.82 mg/ml ; 0.044 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.92 |
Solubility | 1.6 mg/ml ; 0.0121 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) |
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) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.16 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 |
2.0 |
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) |
1.76 |
* 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 |
---|---|---|
57% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 20℃;Inert atmosphere; | General procedure: In a round-bottomed flask (50 mL) equipped with <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> [3] (0.8 g, 3.06 mmol), Pd(PPh3)2Cl2 (0.05 g, 0.08 mmol), CuI (0.03 g, 0.15 mmol) and acetonitrile (20 mL), was added 2-methyl-3-butyne-2-ol (0.33 mL, 3.37 mmol) and Et3N (1.71 mL, 12.25 mmol). The mixture was stirred at room temperature for 6-8 h. Upon completion of the reaction (TLC), the mixture was filtered, the solid residue washed with EtOAc and washings added to the filtrate. The combined solution was concentrated under reduced pressure. The oily material obtained was subjected to column chromatography (hexane/ethyl acetate 4:1) to afford the desired product 1a. Propargyl alcohols 1b-1m were prepared by using the same experimental procedure. Among these compounds, 1a and 1d are known. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With silver carbonate; In dimethyl sulfoxide; at 80℃; for 12h;Sealed tube; | General procedure: Propargylic alcohols (1, 0.6 mmol), amines (2, 0.5 mmol), H-phosphine oxides (3, 1 mmol), Ag2CO3 (1 mmol, 2 equiv), and solvent were dissolved in sealed tube and stirring at 80 C for 12 h. After completion of reaction, the mixture was quenched with sodium bicarbonate (20 mL), extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with saturated brine twice, and dried over anhydrous MgSO4. After filtration, the solvent was evaporated in vacuum. The crude product was purified by silica gel chromatography (methylene dichloride:methanol=50:1) to give the desired compounds. |
A105287 [101597-25-5]
1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol
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