Structure of 92-69-3
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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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CAS No. : | 92-69-3 |
Formula : | C12H10O |
M.W : | 170.21 |
SMILES Code : | OC1=CC=C(C2=CC=CC=C2)C=C1 |
MDL No. : | MFCD00002347 |
InChI Key : | YXVFYQXJAXKLAK-UHFFFAOYSA-N |
Pubchem ID : | 7103 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302-H318-H410 |
Precautionary Statements: | P273-P280-P301+P312+P330-P305+P351+P338+P310 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 53.9 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.89 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.2 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.06 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.07 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.09 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.86 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.53 |
Solubility | 0.0504 mg/ml ; 0.000296 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.3 |
Solubility | 0.086 mg/ml ; 0.000505 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.33 |
Solubility | 0.00791 mg/ml ; 0.0000465 mol/l |
Class? Solubility class: Log S scale |
Moderately 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 |
-5.07 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 |
0.0 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) |
1.04 |
* 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 |
---|---|---|
154 mg (91%) | With potassium fluoride;palladium diacetate; In tetrahydrofuran; | EXAMPLE 34 Synthesis of 4-hydroxybiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-bromophenol (173 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 154 mg (91percent) of the title compound. |
154 mg (91%) | With potassium fluoride;palladium diacetate; In tetrahydrofuran; | Example 34 Synthesis of 4-hydroxybiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-bromophenol (173 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 154 mg (91percent) of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In sodium hydroxide; | Example 3. (Synthesis of compound I- 56 in Table 1) According to similar synthetic method as phenyl glycidyl ether in example 1, 4-benzyloxy-4'-(2-methylglycidyloxy) diphenylsulfone was obtained by reacting with <strong>[63134-33-8]4-benzyloxy-4'-hydroxydiphenylsulfone</strong> and 2-methylepichlorohydrin in sodium hydroxide aqueous solution. Five grams of the compound and 2.3 g of p-phenylphenol were similarly reacted as example 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In acetonitrile; at 0 - 80℃; | Step-I: Methyl 2-(biphenyl-4-yloxy)but-2-enoate (intermediate B6-1) [00267] Methyl 2-bromo-2-butenoate (cis/trans) (7.3 g, 40.8 mmol) was added dropwise to a stirring solution of 4-phenylphenol (6.94 g, 40.8 mmol) and K2CO3 (16.91 g, 122 mmol) in acetonitrile (100 mL) at 0 C. After heating at reflux for 16 h at 80 C, the reaction mixture was filtered through a short pad of Celite. The Celite pad was rinsed with acetonitrile prior to concentration of the filtrate under vacuum to afford the title product (11 g, 40.2 mmol, 99% yield) as a light-brownish oil. The crude product was taken to the next step as such. lU NMR (400 MHz, chloroform-d) δ 7.48 - 7.59 (m, 4H), 7.42 (t, J= 7.65 Hz, 2H), 7.32 (d, J= 7.28 Hz, 1H), 6.95 - 7.03 (m, 2H), 6.75 (d, J= 7.03 Hz, 1H), 3.74 (s, 3H), 1.82 (d, J= 7.03 Hz, 3H); MS(ES): m/z 286.2 [M+H20]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With dmap; 2,6-di-tert-butyl-4-methyl-phenol; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; | The 4 - (6-acryloxy-1-hexyloxy) benzoic acid (corporate SYNTHONChemicals) 29.2g (100mmol), 4-hydroxy-biphenyl 17.0g (100mmol), DMAP0.6g and a small amount of BHT to the mixed suspension under stirring at room temperature in dichloromethane 200 ml in, adding by DCC24.0g (116mmol) dissolved in the dichloromethane 100 ml solution in which a, stirring overnight. Filtering precipitation of urea of DCC, the filtrate for the sequentially 0.5mol/L hydrochloric acid 150 ml, saturated aqueous solution of sodium bicarbonate 150 ml, saturated salt water 150 ml various washing 2 times, after drying with magnesium sulfate, solvent is removed by distillation, recrystallization with ethanol refined, polymerizable compound to obtain a target of (M2) 39.6g (yield 89percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 80℃; for 3h; | General procedure: To a stirred solution of 39 (0.100g, 0.433mmol), appropriate substituted phenol (0.649mmol) and PPh3 (0.182g, 0.693mmol) in anhydrous toluene (5mL) was added DIAD (0.14mL, 0.693mmol) at 80C. After 3h, EtOAc (40mL) was added to the resulting solution. The organic layer was washed with 0.5M aqueous NaOH (40mL) and water (2×40mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash silica gel column chromatography eluting with Hexanes/EtOAc (9:1) or (95:5). |