Structure of 2314-36-5
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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. : | 2314-36-5 |
Formula : | C7H4Cl2O2 |
M.W : | 191.01 |
SMILES Code : | O=CC1=CC(Cl)=C(O)C(Cl)=C1 |
MDL No. : | MFCD00017605 |
InChI Key : | LIYGCLJYTHRBQV-UHFFFAOYSA-N |
Pubchem ID : | 16839 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 43.87 |
TPSA ? Topological Polar Surface Area: Calculated from |
37.3 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.48 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.52 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.51 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.97 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.79 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.25 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.95 |
Solubility | 0.215 mg/ml ; 0.00112 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.95 |
Solubility | 0.215 mg/ml ; 0.00112 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.01 |
Solubility | 0.188 mg/ml ; 0.000986 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 |
-5.68 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) |
1.19 |
* 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 |
---|---|---|
55% | With sulfuryl dichloride; In chloroform;Inert atmosphere; Reflux; | Compound R53 (4.9 g, 40 mmol) was dissolved in 80 ml of dry chloroform, followed by argon gasProtected, heated to reflux, slowly added dropwise a solution of 20 ml of sulfonyl chloride (6.4 ml, 80 mmol) in chloroform, and then refluxed overnight. The reaction solution was spin-dried and purified on a silica gel column. Yield 4.2g (55percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; | 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2CI2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77g, 22percent). LC-MS: tR = 0.82 min. |
22% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; | 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2Cl2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77 g, 22percent). LC-MS: tR=0.82 min. |
22% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; | 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CHaCk, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77g, 22percent). LC-MS: tR = 0.82 min. |
22% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; | 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2Cl2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77 g, 22percent). LC-MS: tR = 0.82 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hexamethylenetetramine;Reflux; | General procedure: A solution of the selected phenol (10 mmol) and hexamethylenetetramine (11 mmol, 1.550 g) in trifluoroacetic acid (10 mL) was stirred and heated at reflux overnight. After cooling to room temperature, the crude product mixture was evaporated under reduced pressure and the yellow residue obtained was poured into distilled water and crushed ice. The cream-colored solid that precipitated was filtered under reduced pressure, washed with distilled water and dried at room temperature under vacuum, yielding the desired compound as a white solid. See, e.g., (Scheme 1, Figure 2). Yield: 60percent, 940 mg; |
quaternary ammonium compounds, such asN-alkyl-N,N-dimethylbenzyl ammonium chloride and...cetylpyridinium chloridediguanidinepolybiguanide1,2-dibromo-2,4-dicyanobutane3,5-dichloro4-hydroxybenzaldehydeethylene glycol hemiformaldichlorophen2,2-dibromo-3-nitrilopropionic acid amide... | ||
Stage A 3,5-dichloro-4-hydroxy-benzaldehyde 15 g of hydroxy-4-benzaldehyde in 75 ml of thionyl chloride was stirred at reflux for 36 hours and then the reaction medium was evaporated under reduced pressure to obtain the expected crude product which was crystallized from an acetone/n-pentane mixture to obtain 20 g of an 85/15 mixture of dichlorinated/monochlorinated product. Crystallization from a cyclohexane/acetone mixture (4/1) allowed the pure dichlorinated product to be obtained with a Rf=0.15 (dichloromethane/methanol 99/1). IR (CHCl3) |
Quaternary ammonium compounds such asN-alkyl-N,N-dimethylbenzylammonium chloride anddi-n-decyldimethylammonium chlorideCetylpyridinium chlorideDiguanidine1,2-Dibromo-2,4-dicyanobutane3,5-Dichloro-4-hydroxybenzaldehydeEthylene glycol hemiformal |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With piperidine; In ethanol; at 80℃; for 16h;Inert atmosphere; | General procedure: Piperidine (8.7 muL, 0.088 mmol), 3,5-difluoro-4-hydroxybenzaldehyde (69.5 mg, 0.44 mmol) and S3 (100.0 mg, 0.44 mmol) were dissolved in EtOH (2.0 mL). The mixture was heated to 80 oC for 16 h. The orange solid was filtered and washed with 1N HCl and Et2O to afford 3 (114.0 mg, 70percent, mixture of E/Z isomers). |
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