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CAS No. : | 172732-52-4 | MDL No. : | MFCD04039012 |
Formula : | C10H10BNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | REQZFVYFYAZUMG-UHFFFAOYSA-N |
M.W : | 187.00 | Pubchem ID : | 3529602 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 53.14 |
TPSA : | 42.25 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.2 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.75 |
Log Po/w (WLOGP) : | 0.69 |
Log Po/w (MLOGP) : | 0.2 |
Log Po/w (SILICOS-IT) : | 1.06 |
Consensus Log Po/w : | 0.74 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.35 |
Solubility : | 0.829 mg/ml ; 0.00444 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.25 |
Solubility : | 1.04 mg/ml ; 0.00557 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.84 |
Solubility : | 0.273 mg/ml ; 0.00146 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.65 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
82.4% | at 20℃; for 1 h; | 3.69 g (48.5 mmol) of 1,3-propanediol was added to the organic phase obtained in Example 1, and the mixture was stirred at room temperature for 1 hour. After separation of the separated aqueous phase, the solvent was distilled off with an evaporator. 2 ml of toluene and 120 ml of heptane were added to the remaining oily matter to precipitate crystals. The obtained crystals were washed with 30 ml of heptane and then dried, 7.44 g (yield: 82.4percent) of 1,3-propanediol ester (2- (1,3,2-dioxaborinan-2-yl) benzonitrile) of 2-cyanophenylboronic acid was obtained. The crystal contained 0.40percent of 1-phenyl-1- (2,2,6,6-tetramethylpiperidin-1-yl) methylimine |
57.2% | for 20 h; | Step 1: Synthesis of 2-(1,3,2-dioxaborinan-2-yl)benzonitrile 49.0 g (334 mmol) 2-cyanobenzeneboronic acid and 25.9 g (340 mmol) 1,3-propanediol were dissolved in 1 L CH2Cl2 with stirring in a 2 L round bottom flask for 20 h. The solution was then poured over a filter with suction to remove gummy solids. The filtrate was then dried with anhydrous MgSO4 to remove residual water, filtered and evaporated of solvent to give light-colored oil. The oil was then dissolved in CH2Cl2 and purified on a silica gel plug using CH2Cl2 as eluent. The product fractions were evaporated down to give the product as clear oil (35.7 g, 57.2percent yield). |
57.2% | for 20 h; | Step 1: synthesis of 2-(1,3,2-dioxaborainan-2-yl)benzonitrile 49.0 g (334 mmol) 2-cyano-benzeneboronic acid and 25.9 g (340 mmol) 1,3-propanediol and stirred while 2 ℓ 1 ℓ round bottom flask in CH2Cl2 20 hours dongan was dissolved. Then, the solution was poured into a suction filter to remove the solids on the gum. Then, the filtrate was dried over anhydrous MgSO4 and removal of the residue, filtered, to give a lighter colored oil by evaporation of the solvent. Thereafter, the oil was dissolved in CH2Cl2, was purified using CH2Cl2 as eluent on a silica gel plug. Distilling the product fractions to obtain the product (35.7 g, 57.2percent yield) as a clear oil |
20% | for 24 h; Reflux | 2-cyano phenyl boronic acid and 1,3 propanediol was solubilized in anhydrous toluene. The reaction mixture was refluxed in a flask equipped with a Dean-Stark apparatus. After 24 h, the reaction was concentrated under reduced pressure to give colorless oil. The crude product was purified on silica gel (DCM) to give 2-[1-3]dioxaborinan-2-yl-benzonitrile; yield: 20percent; 1H NMR (300 MHz, CDCl3) δ ppm 2.08 (t, J = 5.4 Hz, 2H), 4.21 (q, J = 5.4 Hz, 4H), 5.31 (ls, 2H), 7.45 (td, J1 = 7.5 Hz, J2 = 1.5 Hz, 1H), 7.53 (td, J1 = 7.5 Hz, J2 = 1.5 Hz, 1H), 7.65 (d, J = 7.5 Hz, 1H), 7.85 (d, J = 7.5 Hz, 1H). The 2-[1-3]dioxaborinan-2-yl-benzonitrile was readily solubilized in toluene (0.2 M). To this solution, compound 3e (1eq), PdCl2(dppf) (2percent) and K3PO4 (2 eq) were added. The mixture was refluxed during 2 h, then was concentrated under reduced pressure. The obtained crude product was dissolved in ethyl acetate and washed by HCl 1N. The organic layer was concentrated under reduced pressure and purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (70/30) to give 9 as a yellow powder; purity 99percent; yield: 83percent; mp: 169-170 °C; 1H NMR (300 MHz, CDCl3) δ ppm 1.29 (t, J = 6.9 Hz, 3H), 2.10 (s, 3H), 4.23 (q, J = 6.9 Hz, 2H), 7.61 (td, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.69 (dd, J1 = 7.8 Hz, J2 = 0.9 Hz, 1H), 7.75 (d, J = 8.7 Hz, 2H), 7.82 (td, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H), 7.82 (dd, J1 = 7.8 Hz, J2 = 0.9 Hz, 1H), 7.82 (d, J = 8.7 Hz, 2H), 9.13 (s, 1H), 9.95 (sl, 1H); 13C NMR (75 MHz, CDCl3) δ ppm 15.0, 23.9, 60.8, 110.2, 110.9, 119.3, 119.5, 129.3, 130.1, 130.2, 132.7, 134.5, 134.8, 137.1, 139.6, 144.2, 148.4, 162.7, 169.6; LCMS (EI (+)) m/z = 389 [M + H] +. HRMS (EI) calcd for C21H18N4O2 [M + H]+ 375.14517. Found 375.14454. |
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