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CAS No. : | 123320-44-5 | MDL No. : | MFCD23135734 |
Formula : | C11H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HHYMUVTUFJYDSQ-UHFFFAOYSA-N |
M.W : | 205.21 | Pubchem ID : | 5324208 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.18 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 53.61 |
TPSA : | 55.49 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) : | -6.61 cm/s |
Log Po/w (iLOGP) : | 2.41 |
Log Po/w (XLOGP3) : | 1.32 |
Log Po/w (WLOGP) : | 1.44 |
Log Po/w (MLOGP) : | 1.0 |
Log Po/w (SILICOS-IT) : | 2.11 |
Consensus Log Po/w : | 1.66 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.22 |
Solubility : | 1.23 mg/ml ; 0.00599 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.09 |
Solubility : | 1.68 mg/ml ; 0.0082 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.74 |
Solubility : | 0.0376 mg/ml ; 0.000183 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.83 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | 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 |
---|---|---|
67% | With dipyridinium dichromate In dichloromethane at 20℃; for 16 h; | Example 7B (0.45 g, 2.19 mmol) was dissolved in dichloromethane and treated with solid pyridinium dichromate (PDC, 1.24 g, 3.3 mmol). The resulting slurry was stirred at room temperature for 16 hours and then filtered through diatomaceous earth eluting with dichloromethane (3χ75 mL). The organic layer was washed with 1 /V aqueous HC1 (2x50 mL) and 10percent aqueous NaCl (100 mL), dried over anhydrous Na2S04(s), filtered, and concentrated in vacuo leaving a brown oil. The oil was purified by silica gel chromatography eluting with a gradient of hexane/ethyl acetate (95/5 to 70/30) to give the title compound as a tan solid (0.3 g, 67percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | at 15℃; for 3 h; | To a solution of methyl 3-benzyloxyisoxazole-5-carboxylate (2.33 g, 9.99 mmol, 1.00 eq) in methanol (50 mL) was added sodium borohydride (756 mg, 19.98 mmol, 2.00 eq) in portions. The resulting mixture was stirred at 15 °C for 3 hr. TLC (petroleum ether : ethyl acetate = 5 : 1) showed the reaction was completed. The mixture was poured into hydrochloric acid (0.2 M, 200 niL), and extracted with ethyl acetate (150 niL x 2). The combined organic layers were washed with saturated brine (200 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford (3-benzyloxyisoxazol-5-yl)methanol (1.85 g, 9.02 mmol, 90percent yield) as colorless oil. LC-MS (ESI) m/z: 206.1 [M+H+]. |
87% | Stage #1: at 20℃; for 20 h; Stage #2: With hydrogenchloride In water at 20℃; for 2 h; |
Example 7A (0.52g, 2.23 mmol) was dissolved in methanol (25 mL) and treated with solid sodium borohydride (0.1 lOg, 2.90 mmol). The solution began foaming which subsidedapproximately 10 minutes later. The reaction mixture was stirred at room temperature for 20 hours. Methanol (50 mL) and 1 N aqueous HC1 (100 mL) were then added to the mixture which was subsequently stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo. The aqueous layer was extracted with dichloromethane (3x 100 mL). The combined organic washes were dried over anhydrous Na2S04(s), filtered and concentrated in vacuo leaving the title compound as a clear oil (0.4 g, 87percent). |
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