Structure of 19500-61-9
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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. : | 19500-61-9 |
Formula : | C10H13NO |
M.W : | 163.22 |
SMILES Code : | COC1=CC2=C(C=C1)CCCN2 |
MDL No. : | MFCD08544271 |
InChI Key : | WDKNRIQDGSVRBO-UHFFFAOYSA-N |
Pubchem ID : | 16244388 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 52.83 |
TPSA ? Topological Polar Surface Area: Calculated from |
21.26 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.11 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.26 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.48 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.71 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.41 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.99 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.58 |
Solubility | 0.43 mg/ml ; 0.00263 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.34 |
Solubility | 0.741 mg/ml ; 0.00454 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.4 |
Solubility | 0.0654 mg/ml ; 0.000401 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) |
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 |
-5.69 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 |
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) |
1.62 |
* 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 |
---|---|---|
78% | With hydrogen;platinum(IV) oxide; In methanol; at 20℃; for 16h; | A solution of compound 2-2(12.5 g, 79 mmol) and Pt02 (l . lg, 4.8mmol) in MeOH (500 mL) was stirred at rt for 16 hrs under an atmosphere of H2. The reaction mixture was filtered through Celite.(R).545 and the filtrate was concentrated. The residue was purified by silica gel column chromatography (EtOAc/petroleum ether = 1/8 (v/v)) to give compound 2-3 (9.0 g, 78percent yield) as a yellow oil. LC-MS (ESI): mlz 164 [M+H]+; NMR (500 MHz, CDC13): delta 6.84 (d, J = 8.5 Hz, 1 H), 6.20 (dd, J, = 8.5 Hz, J2 = 2.5 Hz, 1H), 6.04 (d, J = 2.5 Hz, 1H), 3.73 (s, 3H), 3.26 - 3.28 (m, 2H), 2.69 (t, J = 6.5 Hz, 2H), 1.91 (dd, Ji = 6.5 Hz, J2 = 4.5 Hz, 2H) ppm. |
73% | With hydrogen;platinum(IV) oxide; In methanol; at 20℃; | To a solution of <strong>[4964-76-5]7-methoxyquinoline</strong> (2.0 g, 12.56 mmol) in methanol (60 ml) was added Pt02 (180 mg, 0.79 mmol). H2 (g) was introduced into above solution and the reaction was stirred overnight at room temperature and then the solids were filtered off. The organics were concentrated in vacuo to give a residue, which was purified by silica gel column chromatography with 3 percent ethyl acetate in petroleum ether to afford 7-methoxy-l,2,3,4-tetrahydroquinoline as a light yellow oil (1.5 g, 73percent).LC/MS (ES, m/z): [M+H]+ 164.0'H-NMR (300 MHz, CD3OD): delta 6.76 (d, / = 8.4 Hz, 1H), 6.09 - 6.17 (m, 2H), 3.69 (s, 1H), 3.19 - 3.23 (m, 2H), 2.64 - 2.69 (t, / = 6.6 Hz, 2H), 1.85 - 1.93 (m, 2H) |
38% | With platinum(IV) oxide; hydrogen; In methanol; at 76℃; under 775.743 Torr; for 12h; | To a solution of <strong>[4964-76-5]7-methoxyquinoline</strong> (800 mg, 5.03 mmol) in MeOR (8 mL) was added Pt02(137 mg, 0.6 mmol). The mixture was heated to 76 °C for 12 h under a hydrogen atmosphere(15 psi). After cooling the reaction to room temperature, the mixture was concentrated invacuo. The crude residue was purified by silica gel chromatography (petroleum ether EtOAc10: 1) to give the title compound (350 mg, 38percent) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12 mg (88%) | With N2; In dichloromethane; | 1,2,3,4-tetrahydro-7-hydroxyquinoline In a flame dried 100 mL rb flask equivuipped with a magnetic stir bar and a N2 gas inlet was dissolved 1,2,3,4-tetrahydro-7-methoxyquinoline (14.0 mg, 85.8 mumol) in CH2 Cl2 (~3 mL). The solution was cooled to -78 C. under a blanket of N2 and a 1.0M solution of BBr3 in CH2 Cl2 (0.25 mL, 250 mumol, 3 equiv) was added via syringe. The solution stirred at -78 C. for 1 h, warmed to 0 C. for 1 h and rt for 2 h. The reaction was quenched with H2O (2 mL), extracted with CH2 Cl2 (3*20 mL), washed with brine (2*20 mL), dried (Na2 SO4) and concentrated in vacuo to afford 12 mg (88%) of the desired adduct as a yellow oil. |
12 mg (88%) | With N2; boron tribromide; In dichloromethane; | 1,2,3,4-tetrahydro-7-hydroxyquinoline In a flame dried 100 mL rb flask equivuipped with a magnetic stir bar and a N2 gas inlet was dissolved 1,2,3,4-tetrahydro-7-methoxyquinoline (14.0 mg, 85.8 mumol) in CH2 Cl2 (~3 mL). The solution was cooled to -78 C. under a blanket of N2 and a 1.0M solution of BBr3 in CH2 Cl2 (0.25 mL, 250 mumol, 3 equiv) was added via syringe. The solution stirred at -78 C. for 1 h, warmed to 0 C. for 1 h and rt for 2 h. The reaction was quenched with H2 O (2 mL), extracted with CH2 Cl2 (3*20 mL), washed with brine (2*20 mL), dried (Na2 SO4) and concentrated in vacuo to afford 12 mg (88%) of the desired adduct as a yellow oil. |
12 mg (88%) | With N2; In dichloromethane; | 1,2,3,4-tetrahydro-7-hydroxyquinoline. In a flame dried 100 mL rb flask equivuipped with a magnetic stir bar and a N2 gas inlet was dissolved 1,2,3,4-tetrahydro-7-methoxyquinoline (14.0 mg, 85.8 mumol) in CH2 Cl2 (~3 mL). The solution was cooled to -78 C. under a blanket of N2 and a 1.0M solution of BBr3 in CH2 Cl2 (0.25 mL, 250 mumol, 3 equiv) was added via syringe. The solution stirred at -78 C. for I h, warmed to 0 C. for I h and rt for 2 h. The reaction was quenched with H2 O (2 mL), extracted with CH2 Cl2 (3*20 mL), washed with brine (2*20 mL), dried (Na2 SO4) and concentrated in vacuo to afford 12 mg (88%) of the desired adduct as a yellow oil. |
12 mg (88%) | With N2; In dichloromethane; | 1,2,3,4-tetrahydro-7-hydroxyquinoline. In a flame dried 100 mL rb flask equivuipped with a magnetic stir bar and a N2 gas inlet was dissolved 1,2,3,4-tetrahydro-7-methoxyquinoline (14.0 mg, 85.8 mumol) in CH2 Cl2 (~3 mL). The solution was cooled to -78 C. under a blanket of N2 and a 1.0M solution of BBr3 in CH2 Cl2 (0.25 mL, 250 mumol, 3 equiv) was added via syringe. The solution stirred at -78 C. for 1 h, warmed to 0 C. for 1 h and rt for 2 h. The reaction was quenched with H2O (2 mL), extracted with CH2 Cl2 (3*20 mL), washed with brine (2*20 mL), dried (Na2 SO4) and concentrated in vacuo to afford 12 mg (88%) of the desired adduct as a yellow oil. |
12 mg (88%) | With N2; In dichloromethane; | 1,2,3,4-tetrahydro-7-hydroxyquinoline In a flame dried 100 mL rb flask equivuipped with a magnetic stir bar and a N2 gas inlet was dissolved 1,2,3,4-tetrahydro-7-methoxyquinoline (14.0 mg, 85.8 tumol) in CH2 Cl2 (~3 mL). The solution was cooled to -78 C. under a blanket of N2 and a 1.0M solution of BBr3 in CH2 Cl2 (0.25 mL, 250 tamol, 3 equiv) was added via syringe. The solution stirred at -78 C. for lh, warmed to 0 C. for 1 h and rt for 2 h. The reaction was quenched with H2 O (2 mL), extracted with CH2 Cl2 (3*20 mL), washed with brine (2*20 mL), dried (Na2504) and concentrated in vacuo to afford 12 mg (88%) of the desired adduct as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium carbonate; In ethanol; at 20℃; for 24h;Irradiation; | In the reactor, 100 mg of substrate 7-methoxy-1,2,3,4-tetrahydroquinoline, 10 mg of boron nitrocarbon photocatalyst, 3 mlOf ethanol and 1.2 equivalents of potassium carbonate, the reaction was stirred at room temperature light illumination 24h, after the reaction was extracted with ethyl acetate, combined with The organic phase was dried, filtered, and the solvent was distilled off under reduced pressure to give a crude product. The column was eluted with petroleum ether: 3: 1 by volume Ethyl acetate mixed solvent, yield 89percent. |
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