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CAS No. : | 929626-18-6 | MDL No. : | MFCD09751432 |
Formula : | C9H11BO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 193.99 g/mol | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 52.51 |
TPSA : | 66.76 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.74 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.04 |
Log Po/w (WLOGP) : | -0.54 |
Log Po/w (MLOGP) : | 0.52 |
Log Po/w (SILICOS-IT) : | -0.39 |
Consensus Log Po/w : | 0.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.82 |
Solubility : | 2.96 mg/ml ; 0.0152 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.03 |
Solubility : | 1.8 mg/ml ; 0.00928 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.75 |
Solubility : | 3.41 mg/ml ; 0.0176 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.08 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
Stage #1: methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate With sodium periodate In tetrahydrofuran; water for 0.25h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 4h; | ||
466 mg | Stage #1: methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate With sodium periodate; water In tetrahydrofuran at 23℃; for 8h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-methoxycarbonyl-3-methylbenzene With pinacol borane; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In cyclohexane at 80℃; for 24h; Stage #2: With sodium periodate In tetrahydrofuran; water for 0.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 17h; | ||
Multi-step reaction with 2 steps 1.1: 4,4'-di-tert-butyl-2,2'-bipyridine / [Ir(COD)(OMe)]2 / tetrahydrofuran / 16 h / 80 °C 2.1: sodium periodate / tetrahydrofuran; H2O / 0.25 h 2.2: HCl / H2O; tetrahydrofuran / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With 2,6-dimethylpyridine; air; 1-decanoic acid In toluene at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: (3-methoxycarbonyl-5-methyl-phenyl)boronic acid With sodium hydroxide In methanol at 23℃; for 0.25h; Inert atmosphere; Stage #2: With silver trifluoromethanesulfonate In methanol at 0℃; for 0.5h; Inert atmosphere; Stage #3: With Selectfluor In acetone at 23℃; for 1h; Inert atmosphere; Molecular sieve; regiospecific reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: 1-methoxycarbonyl-3-methylbenzene; bis(pinacol)diborane In tetrahydrofuran at 23 - 80℃; Stage #2: With sodium periodate; water In tetrahydrofuran at 23℃; for 8h; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 1h; | 62 Example 62. 3-Methoxycarbonyl-5-methylphenyl boronic acid (S52)To m-toluic acid methyl ester (451 mg, 3.00 mmol, 1.00 equiv) in THF (6.0 mL) at 23 0C was added [Ir(COD)(OMe)]2 (10 mg, 0.015 mmol, 0.50 mol%), dtbpy (8.0 mg, 0.030 mmol, 1.0 mol%) and bis(pinacolato)diborone (610 mg, 2.40 mmol, 0.800 equiv). After stirring for 24 hr at 80 0C, the reaction mixture was added to H2O (6.0 mL) and NaIO4 (3.21 g, 15.0 mmol, 5.00 equiv). After stirring for 8.0 hr at 23 0C, the reaction mixture was added to IN HCl aq (10 mL) and was further stirred for 1.0 hr. To the reaction mixture was added EtOAc (20 mL) and the phases were separated. The aqueous phase was extracted with EtOAc (2 x 20 mL). The combined organic phases are washed with brine (20 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel eluting with hexanes/EtOAc 7:3 (v/v) to afford 466 mg of the title compound as a colorless solid (80% yield). R/ = 0.15 (hexanes/EtOAc 7:3 (v/v)). NMR Spectroscopy: 1U NMR (500 MHz,OMSO-d6, 23 0C, δ): 8.21 (s, IH), 8.19 (s, 2H), 7.84 (s, IH), 7.79 (s, IH), 3.83 (s, 3H), 2.35 (s, 3H). 13C NMR (125 MHz, OMSO-d6, 23 0C, δ): 166.71, 139.65, 136.97, 134.70 (br), 132.24, 131.14, 128.83, 51.99, 20.82. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: (3-methoxycarbonyl-5-methyl-phenyl)boronic acid With sodium hydroxide In methanol at 23℃; for 0.25h; Inert atmosphere; Stage #2: With silver(I) hexafluorophosphate In methanol at 0℃; for 0.5h; Inert atmosphere; Stage #3: tris(dimethylamino)sulfonium trifluoromethoxide Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); XPhos In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere; | Preparation of intermediate 12 A mixture of 1,4-dioxane and water (3:1, 15 ml) was degassed by bubbling nitrogen gas through the mixture. Intermediate 11(3.00 g, 5.00 mmol) and (3-methoxycarbonyl-5-methyl- phenyl)boronic acid (1 .79 g, 6.50 mmol) were dissolved. 2-Dicyclohexylphosphino-2’,4’,6’- triisopropylbiphenyl (Xphos) (143 mg, 0.30 mmol), tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.10 mmol), and potassium phosphate tribasic (5.03 g, Seq.) were added and themixture was stirred under nitrogen gas at 90°C for 16 hours. The reaction mixture was cooled, passed over celite and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography over silica gel using dichloromethane and methanol as eluents (gradient elution from 0% to 10% methanol). The product fractions were collected and the solvent was removed under reduced pressure.Yield: 3.00 g of intermediate 12 (90%)LCMS method 1: MH = 569 (MW-Boc), RT = 1.419 mm |
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