Structure of 2,5-Diphenyloxazole
CAS No.: 92-71-7
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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.
Synonyms: PPO; DPO; POP
4.5
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 92-71-7 |
Formula : | C15H11NO |
M.W : | 221.25 |
SMILES Code : | C1(C2=CC=CC=C2)=NC=C(C3=CC=CC=C3)O1 |
Synonyms : |
PPO; DPO; POP
|
MDL No. : | MFCD00005306 |
InChI Key : | CNRNYORZJGVOSY-UHFFFAOYSA-N |
Pubchem ID : | 7105 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H319-H413 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 17 |
Num. arom. heavy atoms | 17 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 67.38 |
TPSA ? Topological Polar Surface Area: Calculated from |
26.03 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.84 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
4.67 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
4.01 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.76 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.99 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.65 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.76 |
Solubility | 0.00383 mg/ml ; 0.0000173 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-4.94 |
Solubility | 0.00252 mg/ml ; 0.0000114 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-6.28 |
Solubility | 0.000116 mg/ml ; 0.000000525 mol/l |
Class? Solubility class: Log S scale |
Poorly 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) |
Yes |
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 |
-4.33 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 |
0.0 |
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<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.85 |
* 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 |
---|---|---|
69% | With copper(l) iodide; sodium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 120℃; for 16h;Inert atmosphere; | General procedure: 5-Aryl oxazole 2 (0.69 mmol) and 4-iodobenzene/4-iodobenzoic acid (0.83 mmol) were taken in dry DMF (10 mL). Copper iodide (0.69 mmol) and triphenyl phosphine (0.2mmol) were then added sequentially. To this mixture sodiumc arbonate (1.39 mmol) in little excess was added at one portion and the resulting mixture was stirred at 120 C for 16 h under inert atmosphere (N2). The whole mixture was concentrated by removing excess DMF using vacuum pump and then it was diluted with dichloromethane (30 mL). The entire organic solution was sequentially washed with water (15 mL × 3), 3 % HCl (15 mL) and half saturated brine solution (20 mL). Finally the organic layer was dried over anhydrous sodium sulphate. It was then concentrated in vacuo and was purified by column chromatography using petroleum ether-ethyl acetate (3:1) as eluent to get the product as colourless solid. The formation of the product was further confirmed by spectroscopic data. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With bis(1,5-cyclooctadiene)nickel(0); caesium carbonate; 1,2-bis-(dicyclohexylphosphino)ethane; In para-xylene; at 140℃; for 21h;Glovebox; Sealed tube; | General procedure: Ni(COD)2, ligand (dcype or dcypt), base (Cs2CO3 or K3PO4), and azole were weighed into in an oven dried 20 mL scintillation vial in the glove box. A xylene solution of the aryl electrophile (pivalates, mesylates or carbamates) was added to the reaction mixture. The reaction vial was sealed with a Teflon lined cap, taken out of the glove box and the reaction mixture was allowed to stir at the indicated temperature for the indicated time. The reaction mixture was cooled to room temperature and filtered through a 1.0 inch plug of silica gel, eluting with Et2O (125 mL). The filtrate was concentrated and chromatographed on a silica gel column to afford the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With bis(1,5-cyclooctadiene)nickel(0); 3,4-thiene-2,3-diylbis(dicyclohexylphosphine); caesium carbonate; In para-xylene; at 140℃; for 22h;Glovebox; Sealed tube; | General procedure: Ni(COD)2, ligand (dcype or dcypt), base (Cs2CO3 or K3PO4), aryl electrophile (pivalates, mesylates or carbamates) and azole were weighed into in an oven dried 20 mL scintillation vial in the glove box. Xylene was added, the vial was sealed with a Teflon lined cap, taken out of the glove box and the reaction mixture was allowed to stir at the indicated temperature for the indicated time. The reaction mixture was cooled to room temperature and filtered through a 1.0 inch plug of silica gel, eluting with Et2O (125 mL). The filtrate was concentrated and chromatographed on a silica gel column to afford the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With bis(1,5-cyclooctadiene)nickel(0); potassium phosphate; 3,4-thiene-2,3-diylbis(dicyclohexylphosphine); In para-xylene; at 140℃; for 22h;Glovebox; Sealed tube; | General procedure: Ni(COD)2, ligand (dcype or dcypt), base (Cs2CO3 or K3PO4), and azole were weighed into in an oven dried 20 mL scintillation vial in the glove box. A xylene solution of the aryl electrophile (pivalates, mesylates or carbamates) was added to the reaction mixture. The reaction vial was sealed with a Teflon lined cap, taken out of the glove box and the reaction mixture was allowed to stir at the indicated temperature for the indicated time. The reaction mixture was cooled to room temperature and filtered through a 1.0 inch plug of silica gel, eluting with Et2O (125 mL). The filtrate was concentrated and chromatographed on a silica gel column to afford the product. |
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