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CAS No. : | 13020-57-0 | MDL No. : | MFCD00002297 |
Formula : | C13H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SHULEACXTONYPS-UHFFFAOYSA-N |
M.W : | 198.22 | Pubchem ID : | 83050 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 58.34 |
TPSA : | 37.3 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) : | -5.33 cm/s |
Log Po/w (iLOGP) : | 1.85 |
Log Po/w (XLOGP3) : | 3.07 |
Log Po/w (WLOGP) : | 2.62 |
Log Po/w (MLOGP) : | 2.34 |
Log Po/w (SILICOS-IT) : | 2.92 |
Consensus Log Po/w : | 2.56 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.46 |
Solubility : | 0.0682 mg/ml ; 0.000344 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.52 |
Solubility : | 0.0598 mg/ml ; 0.000302 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.29 |
Solubility : | 0.0101 mg/ml ; 0.0000511 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.44 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-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 |
---|---|---|
100% | With hydrogen bromide; acetic acid; for 12h;Reflux; | A solution of 5(9.4g) in AcOH (90ml) and con. HBr (90ml) was heated under reflux for 12h. H2O (300ml) and AcOEt (300ml) was added, the water phase was re-extracted with AcOEt (100ml) and the combined organic phase was washed with brine and dried over Na2SO4 to give 6 as grey solid. (8.8g, 100%), mp 112-114(reference 114-116) |
91% | With water; hydrogen bromide; In acetic acid; at 90℃; for 18h;Large scale; | Step 2: (3-Hydroxyphenyl)(phenyl)methanone 1458 g (6.9 mol) of (3-methoxyphenyl)(phenyl)methanone was dissolved in 2090 mL of AcOH. To this solution, 2320 ml (20.6 mol) of 48% HBr was added and the mixture was stirred at 90 C. for 18 hours. The reaction was monitored by TLC (AcOEt:hex 1:9). After the reaction was completed the mixture was cooled down to RT and poured into ice with stirring. The precipitated solid was filtered, washed with water and dried yielding the title compound as a white solid (1234 g, 91%). 1H NMR (600 MHz, CDCl3); delta 7.80 (m, 2H); 7.58 (m, 1H); 7.47 (m, 2H); 7.39 (m, 1H); 7.28-7.34 (m, 2H); 7.11 (m, 1H); 5.59 (brs, 1H). |
91% | With hydrogen bromide; acetic acid; at 90℃; for 18h;Large scale; | 1458 g (6.9 mol) of (3-methoxyphenyl)(phenyl)methanone was dissolved in 2090 mL of AcOH. To the solution, 2320 ml (20.6 mol) of 48% HBr was added and the mixture was stirred at 90 C for 18 hours. The reaction was monitored by TLC (AcOE hex 1 :9). After reaction was completed the mixture was cooled down to RT and poured into ice with stirring. The precipitated solid was filtered, washed with water and dried yielding the title compound as a white solid (1234 g, 91%).1H NMR (600 MHz, CDCl3); delta 7.80 (m, 2 H); 7.58 (m, 1 H); 7.47 (m, 2 H); 7.39 (m, 1 H); 7.28-7.34 (m, 2 H); 7.1 1 (m, 1 H); 5.59 (brs, 1 H). |
91% | With hydrogen bromide; acetic acid; at 90℃; for 18h;Large scale; | 1458 g (6.9 mol) of (3-methoxyphenyl)(phenyl)methanone was dissolved in 2090 mL of AcOH. To the solution, 2320 mL (20.6 mol) of 48% HBr was added and the mixture was stirred at 90C for 18 hours. The reaction was monitored by TLC(AcOEt:hex 1:9). After reaction was completed the mixture was cooled down to RT and poured into ice with stirring. The precipitated solid was filtered, washed with water and dried yielding the title compound as a white solid (1234 g, 9 1%).1H NMR (600 MHz, CDC13), oe 7.80 (m, 2 H), 7.58 (m, 1 H), 7.47 (m, 2 H), 7.39 (m, 1 H), 7.28-7.34 (m, 2 H), 7.11 (m, 1 H), 5.59 (brs, 1 H). |
91% | With hydrogen bromide; acetic acid; at 90℃; for 18h;Large scale; | Step 2: Preparation of (3-Hydroxyphenyl)(phenyl)methanone (I6b) 1458 g (6.9 mol) of (3-methoxyphenyl)(phenyl)methanone was dissolved in 2090 mL of AcOH. To the solution, 2320 mL (20.6 mol) of 48% HBr was added and the mixture was stirred at 90 C. for 18 hours. The reaction was monitored by TLC (AcOEt:hex 1:9). After reaction was completed the mixture was cooled down to RT and poured into ice with stirring. The precipitated solid was filtered, washed with water and dried yielding the title compound as a white solid (1234 g, 91%). 1H NMR (600 MHz, CDCl3), delta 7.80 (m, 2H), 7.58 (m, 1H), 7.47 (m, 2H), 7.39 (m, 1H), 7.28-7.34 (m, 2H), 7.11 (m, 1H), 5.59 (br s, 1H). |
With hydrogen bromide; | Step 2: (3-Hydroxyphenyl)(phenyl)methanone 1458 g (6.9 mol) of (3-methoxyphenyl)(phenyl)methanone was dissolved in 2090 mL of AcOH. To the solution, 2320 ml (20.6 mol) of 48% HBr was added and the mixture was stirred at 90 C. for 18 hours. The reaction was monitored by TLC (AcOEt:hex 1:9). After reaction was completed the mixture was cooled down to RT and poured into ice with stirring. The precipitated solid was filtered, washed with water and dried yielding the title compound as a white solid (1234 g, 91%). 1H NMR (600 MHz, CDCl3); delta 7.80 (m, 2H); 7.58 (m, 1H); 7.47 (m, 2H); 7.39 (m, 1H); 7.28-7.34 (m, 2H); 7.11 (m, 1H); 5.59 (brs, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium carbonate; potassium iodide; In acetone; for 15h;Reflux; | To a 50 mL round-bottom flask, <strong>[13020-57-0](3-hydroxyphenyl)(phenyl)methanone</strong>(6, 1 mmol, 198.2 mg), ethyl 2-bromopropanoate (7, 217.4 mg, 1.2mmol), KI (17 mg, 0.1 mmol), dry acetone (6 mL) and anhydrous K2CO3(276 mg, 2 mmol) were added, and refluxed for 15 h. The mixture was quenchedwith water (5 mL) and the solution was extracted dichoromethane (10 mL×3). The organic extracts were combined and dried with anhydrous MgSO4,filtered and concentrated to dryness reduced pressure by a rotary evaporator.Then the resulting residue was purified by column chromatography on silica gelto provide the desired product (8, light yellow solid, 285 mg,96% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The following benzophenones and benzhydrols are representative of compounds which are useful in the practice of the present invention: ... 2-chloro-3'-methylthiobenzophenone 2,4'-dichloro-4-nitrobenzophenone 4-methoxy-3-methyl-3'-trifluoromethylbenzophenone 4-methoxy-3-methylbenzophenone 3-hydroxybenzophenone 3-iodobenzophenone 2-nitrobenzophenone 4-carbethoxy-3'-methylbenzophenone ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | at 170℃; for 0.166667h; | Compound 77: {3-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}(phenyl)-methanone; 4-Chloro-6,7-dimethoxyquinoline (112 mg) and <strong>[13020-57-0]3-hydroxybenzophenone</strong> (297 mg) were mixed together, and the mixture was heated at 170C for 10 min. A saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated. The residue was subjected to separation and purification by column chromatography on silica gel using hexane-acetone as a solvent to give the title compound (126 mg, yield 65%). 1H-NMR (CDCl3, 400 MHz): delta 4.05 (s, 3H), 4.07 (s, 3H), 6.53 (d, J = 5.4 Hz, 1H), 7.42 - 7.65 (m, 8H), 7.72 (dd, J = 1.5 Hz, 6.3 Hz, 1H), 7.83 (dd, J = 1.2 Hz, 8.3 Hz, 2H), 8.53 (d, J = 5.1 Hz, 1H) Mass spectrometric value (FD-MS, m/z): 385 (M+) |
65% | Example 128 {3-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}phenylmethanone [181] A mixture of 4-chloro-6,7-dimethoxyquinoline (112 mg) and commercially available <strong>[13020-57-0]3-hydroxybenzophenone</strong> (297 mg) was stirred at 170 C. for 10 minutes, the reaction mixture was then purified by thin layer chromatography on silica gel eluding with hexane/acetone (2/1) to obtain 126 mg of the title compound (yield: 65%). 1 H-NMR (CDCl3, 90 MHz): delta 4.4 (s, 3H), 4.05 (s, 3H), 6.53 (d, J=5.3 Hz, 1H), 7.34~7.88 (m, 11H), 8.53 (d, J=5.3 Hz, 1H) Mass spectrometry data (FD-MS, m/z): 385 (M+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; | To a solution of a-1 (0.990 g, 5.0 mmol), n-pentyl alcohol (0.440 g, 5.0 mmol) and PPh3 (1.574 g, 6.0 mmol) in THF (20 mL) was added DIAD (1.112 g, 5.5 mmol). The solution was stirred at room temperature overnight. Concentration and chromatograph on silica gel (20:1 hexane/EtOAc) gave 0.940 g (70%) of a-2 as colorless oil. 1H NMR (400 MHz, CDCl3) delta7.81 (d, J=8.0 Hz, 2H), 7.59 (t, J=8.0 Hz, 1H), 7.51-7.46 (m, 2H), 7.39-7.31 (m, 3H), 7.13 (m, 1H), 7.14-7.10 (m, 1H), 4.01 (t, J=8.0 Hz, 2H), 1.81 (tt, J=8.0, 8.0 Hz, 2H), 1.57-1.43 (m, 4H), 0.93 (t, J=8.0 Hz, 3H); MS (ES) m/z: 269 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 2h; | [0461] To a solution of (3-hydroxyphenyl) (phenyl) methanone (30. 0 g, 151 mmole) in anhydrous THF (300 mL) at 0 C was slowly added a solution of potassium-t-butoxide (200 mL-1 M in THF, 0.200 mmole), followed by a slow addition of [2- (chloromethoxy) ethyl] (trimethyl) silane (32.1 mL, 182 mmole). After stirring the mixture for 2 h, the solvent was removed in vacuo and the residue redissolved in a mixture OF H20 (200 mL) and EtOAc (200 mL). The aqueous layer was further extracted with EtOAc (2 X 100 mL). The combined extracts were washed with H2O (200 mL), 0.1 N HC1 (500 mL), brine (100 mL), dried over MGS04, filtered and concentrated IN VACUUM to give an orange oil. The crude product was redissolved in hexanes and filtered through a silica-gel plug to give the product as an impure pale yellow oil which is carried on without further purification: ESHRMS M/Z 329.1586 (M+H, CL9H2503SI, CALC D 329.1567). |
Tags: 13020-57-0 synthesis path| 13020-57-0 SDS| 13020-57-0 COA| 13020-57-0 purity| 13020-57-0 application| 13020-57-0 NMR| 13020-57-0 COA| 13020-57-0 structure
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H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
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H362 | May cause harm to breast-fed children |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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