Structure of 6317-56-2
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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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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'.
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CAS No. : | 6317-56-2 |
Formula : | C13H12OS |
M.W : | 216.30 |
SMILES Code : | OCC1=CC=C(SC2=CC=CC=C2)C=C1 |
MDL No. : | MFCD04108413 |
InChI Key : | PGOAWMRWDZJQTB-UHFFFAOYSA-N |
Pubchem ID : | 80593 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.08 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 63.13 |
TPSA ? Topological Polar Surface Area: Calculated from |
45.53 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.64 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.11 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.18 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.61 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.48 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.2 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.53 |
Solubility | 0.0632 mg/ml ; 0.000292 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.73 |
Solubility | 0.0399 mg/ml ; 0.000184 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.86 |
Solubility | 0.00297 mg/ml ; 0.0000137 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) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
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 |
-5.41 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<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.53 |
* 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 |
---|---|---|
97.7% | With pyridine; thionyl chloride; In dichloromethane; at 20 - 25℃; for 2h;Cooling with ice; | 518.0 g of 4-phenylmercaptobenzyl alcohol, 147 ml of pyridine and 2444 ml of dichloromethane were charged into a 5000 mL reaction flask at room temperature (25 ° C.), and the mixture was cooled in ice water to control the temperatureThionyl chloride was added dropwise at 20-24 ° C and the mixture was stirred at room temperature (25 ° C) for 2 hours. TLC (n-hexane: ethyl acetate = 10: 1) was carried out to the end of the reaction. Washed with water, neutralized with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure (pressure 1720 Pa, temperature 25 ° C) to dryness. Methylene chloride was recovered to obtain 548.0 g of brownish red oil with a yield of 97.7percent and HPLC purity of 99.66 percent. (Frozen to about -10 curable). |
97.7% | With pyridine; thionyl chloride; In dichloromethane; at 20 - 25℃; for 2h; | 51 8.0 g of 4-phenylmercaptobenzyl alcohol at room temperature (25 °C),147 ml of pyridine and 2444 ml of dichloromethane were placed in a 5000 mL reaction flask, and thionyl chloride was added dropwise at a temperature of 20 to 24 °C under ice-cooling, and stirred at room temperature (25 °C) for 2 hours. Thin layer detection (n-hexane: acetic acid) Ethyl ester = 10:1) to the end of the reaction. The mixture was washed with water until neutral, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated to dryness under reduced pressure (pressure: 1720 Pa, temperature 25 °C), and dichloromethane was recovered to give a brownish red oil, 548.0 g, yield 97.7percent, HPLC purity: 99.66percent. (Chilled to about -10 °C to cure). |
96.7% | With pyridine; thionyl chloride; In dichloromethane; at 20 - 24℃; for 2.5h; | The 4-benzoquinone benzyl alcohol, pyridine, and dichloromethane were put into the reaction flask at room temperature (25 °C), ice-cooled and cooled at 20-24 °C, thionyl chloride was added dropwise, and the mixture was stirred at 25° C for 2 hours. Thin layer detection (n-hexane:ethyl acetate=10:1) to the end of the reaction, washing with water to neutrality, drying the dichloromethane layer over anhydrous magnesium sulfate, filtering, and depressurizing the filtrate (pressure 1720 Pa, temperature 25 °C) To dryness, the methylene chloride was recovered to give a brown-red oil (frozen to about -10 °C or so). See Table 4 for details |
With thionyl chloride; sodium hydrogencarbonate; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; | 2) Dissolving 3.0 g of 1-hydroxymethyl-4-phenylthiobenzene in 15 ml of methylene chloride, 1.5 ml of thionyl chloride was added while stirring in ice-cooling. After stirring for 1 hour, the reaction mixture was washed in ice water (10 ml*3), and 50 ml of methylene chloride was added. The mixture was sequentially washed with aqueous solution of 5percent sodium hydrogencarbonate (5 ml*3) and saturated brine (30 ml*2), and dried with anhydrous sodium sulfate, and concentrated in vacuo, thereby obtaining 1-chloromethyl-4-phenylthiobenzene (3.0 g). NMR (CDCl3) delta: 7.25~7.35 (m, 9H), 4.54 (s, 2H) | |
With thionyl chloride; In dichloromethane; | (2) The 1-hydroxymethyl-4-phenylthiobenzene (3.0 g) is dissolved in methylene chloride (15 ml), and thereto is added with stirring thionyl chloride (1.5 ml) under ice cooling. The mixture is stirred for one hour, and the reaction mixture is washed with ice water (10 ml*3), and thereto is added methylene chloride (50 ml). The mixture is washed in order with 5percent aqueous sodium hydrogen carbonate solution (5 ml*3) and saturated aqueous sodium chloride solution (30 ml*2), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 1-chloromethyl-4-phenylthiobenzene (3.0 g). NMR (CDCl3) delta: 7.25-7.35 (m, 9H), 4.54 (s, 2H) |
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