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CAS No. : | 1780-17-2 | MDL No. : | MFCD00086626 |
Formula : | C10H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HREHOXSRYOZKNT-UHFFFAOYSA-N |
M.W : | 159.18 | Pubchem ID : | 73196 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.87 |
TPSA : | 33.12 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.32 cm/s |
Log Po/w (iLOGP) : | 1.81 |
Log Po/w (XLOGP3) : | 1.34 |
Log Po/w (WLOGP) : | 1.58 |
Log Po/w (MLOGP) : | 1.22 |
Log Po/w (SILICOS-IT) : | 2.31 |
Consensus Log Po/w : | 1.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.22 |
Solubility : | 0.955 mg/ml ; 0.006 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.64 |
Solubility : | 3.67 mg/ml ; 0.0231 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.52 |
Solubility : | 0.0483 mg/ml ; 0.000303 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.22 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
73% | With sodium tetrahydroborate In tetrahydrofuran at 20 - 35℃; for 0.5 h; | Methyl quinoline 2-carboxylate 2 (5 g, 26.8 mmol) in solution in THF (30 mL) was added, at room temperature, to a solution of NaBH4 (710 mg, 18.8 mmol) in THF (20 mL). The mixture was stirred at 35 °C for 30 min. Then, at 35 °C, methanol (2.5 mL) was added followed by warm water (30 mL), and finally ethyl acetate (20mL). The organic layer was washed with water (2×30 mL). The organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude yellow-blue residue was purified through a silica gel column chromatography (AcOEt/MCH: 60/40). White solid; 73percent yield; mp 135 °C (dec); 1H NMR (300 MHz, CDCl3) 4.68 (1H, s, OH), 4.95 (2H, s, CH2), 7.31 (1H, m, CHar), 7.55 (1H, m, CHar), 7.71 (1H, m, CHar), 7.81 (1H, m, CHar), 8.10 (2H, m, CHar); 13C NMR (75 MHz, CDCl3) 64.25, 118.43, 126.35, 127.55, 127.69, 128.57, 129.81, 136.86, 146.72, 159.19; Anal. Calcd. for C10H9NO C, 75.45; H, 5.70; N, 8.80. Found C, 75.13; H, 5.56; N, 8.75. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: With sodium tetrahydroborate In methanol for 0.333333 h; Stage #2: With water In methanol |
Example 16 2-(2,6-Dioxo-piperidin-3-yl)-4-(quinolin-2-ylmethoxy)-isoindole-l,3-dioneStep 1 :[207] 2-Quinolinecarbaldehyde (2.00 g, 12.7 mmol) was dissolved in 25 mL of methanol. To this solution was added sodium borohydride (0.24 g, 6.4 mmol) in small portions over a period of 20 minutes. Then 2 mL of water were added and the mixture was evaporated. The residue was dissolved in ethyl acetate (75 mL) and washed with water (3 x 75 mL) and evaporated. The residue was chromatographed in CH2Cl2-methanol gradient, eluting the product at 97:3 CH2Cl2-methanol, and providing 1.7 g of quinolin-2-yl-methanol in 85percent yield; 1H NMR (CDCl3) δ 4.92 (s, 2H), 7.26 (d, J = 2.1 Hz, IH), 7.30-7.57 (m, IH), <n="68"/>7.68-7.75 (m, IH), 7.82 (dd, J = 8.0 Hz, J = 0.9 Hz, IH), 8.07 (d, J = 8.4 Hz, IH), 8.13 (d, J = 8.5 Hz, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With phosphorus tribromide In dichloromethane at 0 - 20℃; | Quinolin-2-ylmethanol 7 (6 g, 37.8 mmol) was dissolved in CH2Cl2 (60 mL). PBr3 (2.14 mL, 22.6 mmol) was carefully added at 0 °C to this solution. The mixture was allowed to return at ambient temperature and was stirred for 30 min. Water (60 mL) was then added followed by a saturated aqueous solution of K2CO3 (40 mL) to obtain a pH=8. The organic phase was washed with brine (2×30 mL), dried over magnesium sulfate, and concentrated under reduced pressure. The crude residue was purified through a silica gel column chromatography (AcOEt/MCH: 20/80). White solid; 83percent yield; mp 55 °C (dec); 1H NMR (300 MHz, DMSO) 4.86 (2H, s, CH2), 7.67 (2H, m, CHar), 7.78 (1H, m, CHar), 7.99 (2H, m, CHar), 8.40 (1H, m, CHar); 13C NMR (75 MHz, DMSO) 35.67, 122.10, 127.46, 127.54, 128.34, 129.07, 130.53, 138.37, 147.36, 157.67; HRMS (ESI) m/z calculated for C10H9NBr [M+H]+: 221.99129, found: 221.991. |
68% | With dibromo sulfoxide In toluene at 110℃; for 1 h; | PREPARATION 302-(Bromomethyl)quinolineThe title compound of Preparation 29 (3.68 g, 23.1 mmol) was suspended in 60 ml toluene. Thionyl bromide (12.0 g, 57.8 mmol) was slowly added and the mixture was heated at 110°C for 1 h. The mixture was concentrated under reduced pressure and the residue was partitioned between water and dichloromethane. The aqueous phase was basified with potassium carbonate and extracted three times with dichloromethane. The combined organics were washed with water, brine and dried over sodium sulphate and evaporated. The residue was purified by column chromatography (ethyl acetate-hexane, 5:95) to give 3.5 g (15.8 mmol, 68percent) of the title compound as a solid. Purity 100percent.1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.72 (s, 2 H), 7.54 - 7.62 (m, 2H), 7.70 - 7.79 (m, 1 H), 7.83 (d, J=8.21 Hz, 1 H), 8.08 (d, J=8.21 Hz, 1 H),8.19 (d, J=8.60 Hz, 1 H).HPLC/MS (9 min) retention time 5.45 min.LRMS: m/z 224 (M+1). |
68% | Stage #1: With dibromo sulfoxide In toluene at 110℃; for 1 h; Stage #2: With potassium carbonate In water |
The title compound of Preparation 29 (3.68 g, 23.1 mmol) was suspended in 60 ml toluene. Thionyl bromide (12.0 g, 57.8 mmol) was slowly added and the mixture was heated at 110C for 1 h. The mixture was concentrated under reduced pressure and the residue was partitioned between water and dichloromethane. The aqueous phase was basified with potassium carbonate and extracted three times with dichloromethane. The combined organics were washed with water, brine and dried over sodium sulphate and evaporated. The residue was purified by column chromatography (ethyl acetate-hexane, 5:95) to give 3.5 g (15.8 mmol, 68percent) of the title compound as a solid. Purity 100percent. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.72 (s, 2 H), 7.54 - 7.62 (m, 2 H), 7.70 - 7.79 (m, 1 H), 7.83 (d, J=8.21 Hz, 1 H), 8.08 (d, J=8.21 Hz, 1 H), 8.19 (d, J=8.60 Hz, 1 H). HPLC/MS (9 min) retention time 5.45 min. LRMS: m/z 224 (M+1). |
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