Structure of 4086-73-1
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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.
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CAS No. : | 4086-73-1 |
Formula : | C13H22ClN |
M.W : | 227.77 |
SMILES Code : | CCCCCCCC[N+]1=CC=CC=C1.[Cl-] |
MDL No. : | MFCD08458952 |
InChI Key : | OVIYAWWBKPWUOH-UHFFFAOYSA-M |
Pubchem ID : | 77708 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.62 |
Num. rotatable bonds | 7 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 69.54 |
TPSA ? Topological Polar Surface Area: Calculated from |
3.88 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
-2.77 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-1.12 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.34 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.21 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.43 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.62 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.38 |
Solubility | 94.8 mg/ml ; 0.416 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
1.53 |
Solubility | 7710.0 mg/ml ; 33.8 mol/l |
Class? Solubility class: Log S scale |
Highly soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.43 |
Solubility | 0.00854 mg/ml ; 0.0000375 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
Low |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
Yes |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
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 |
-8.48 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) |
1.46 |
* 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 |
---|---|---|
52% | at 85℃; for 24.0h; | Pyridine (0.4 mol) and 1-chlorobutane (or 1-chlorohexane or 1-chlorooctane) (0.4 mol) were placed into a 250 cm3 round bottom flask equipped with an electric heat-jacket and vigorously stirred using a magnetic stirrer for 24 h; at 75 C ([C4-py]Cl) or 85 C ([C6-py]Cl and [C8-py]Cl). [C4-py]Cl and [C6-py]Cl, obtained in the form of the white solids directly after synthesis, were washed in Schlenk apparatus with diethyl ether (4 × 50 cm3) and hexane (4 × 50 cm3) and dried by nitrogen stream. [C8-py]Cl obtained in the form of a transparent yellow, dense, and viscous liquid was cooled to room temperature and extracted by turns with diethyl ether (4 × 50 cm3) and hexane (4 × 50 cm3) and dried by nitrogen stream. Yields: 77% for [C4-py]Cl, 39% for [C6-py]Cl, and 52% for [C8-py]Cl. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With pyridine; sulfuric acid; sodium hydrogencarbonate; In hexane; water; | EXAMPLE 8 In a one liter four-necked flask equipped with a stirrer, a thermometer, a gas-inlet tube and a dropping funnel which had been replaced with nitrogen, potassium tert.-butoxide (112.1 g, 1 mole) and hexane (600 ml) were charged. Through a mixture in the flask, carbon dioxide gas (26.9 liters, 1.2 moles) was bubbled at -10 to 0 C. over one hour while stirring. Then, to the resulting slurry form mixture, N-n-octylpyridinium chloride (11.4 g, 0.05 moles) and pyridine (11.4 g) were charged at 10 to -5 C. and then methanesulfonyl chloride (57.3 g, 0.5 mole) was dropwise added at the same temperature, followed by stirring at the same temperature for one hour. After the reaction, 5% sulfuric acid (250 ml) was added to the reaction mixture, and the mixture was stirred for 30 minutes, kept standing and separated. The resulting organic layer was washed with a 5% aqueous solution of sodium bicarbonate and water successively and concentrated under reduced pressure at 35 to 40 C. to obtain colorless liquid di-tert.-butyl dicarbonate (98.2 g). Yield, 90%. This product was analyzed by gas chromatography to find that a purity was 99.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sulfuric acid; sodium hydrogencarbonate; In hexane; water; | EXAMPLE 20 In a one liter four-necked flask equipped with a stirrer, a thermometer, a gas-inlet tube and a dropping funnel which had been replaced with nitrogen, sodium tert.-butoxide (96.1 g, 1 mole) and hexane (600 ml) were charged. Through a mixture in the flask, carbon dioxide gas (26.9 liters, 1.2 moles) was bubbled at -10 to 0 C. over one hour while stirring. Then, to the resulting slurry form mixture, N-n-octylpyridinium chloride (11.4 g, 0.05 mole) was charged at -10 to -5 C. and then methanesulfonyl chloride (57.3 g, 0.5 mole) was dropwise added at the same temperature, followed by stirring at the same temperature for 3 hours. After the reaction, 5% sulfuric acid (250 ml) was added to the reaction mixture, and the mixture was stirred for 30 minutes, kept standing and separated. The resulting organic layer was washed with a 5% aqueous solution of sodium bicarbonate and water successively and concentrated under reduced pressure at 35 to 40 C. to obtain colorless liquid di-tert.-butyl dicarbonate (90.6 g). Yield, 83%. This product was analyzed by gas chromatography to find that a purity was 99.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 20℃;Inert atmosphere; | To the obtained 1-alkylpyridinium chlorides, the equimolar amount of aluminium chloride was added stepwise carefully under a nitrogen atmosphere at room temperature. The mixtures were magnetically stirred and the transparent, slightly brownish chloroaluminate ionic liquids were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 2: In a glass reactor equipped with a magnetic stirring mechanism 1.14 g (5 mmol) <strong>[4086-73-1]N-octylpyridinium chloride</strong>, obtained from step 1, was introduced and 1.22 g (7.5 mmol) of iron chloride (III) anhydrous was added. The mixture was stirred for 20 minutes at room temperature under an inert atmosphere. A dark red liquid was obtained. The spectroscopic characterizations (1H and 13C NMR) confirm the following chemical structure: |