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CAS No. : | 51725-82-7 | MDL No. : | MFCD03424817 |
Formula : | C12H14O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UNULPFKXRJPSCO-UHFFFAOYSA-N |
M.W : | 206.24 | Pubchem ID : | 2760276 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.31 |
TPSA : | 43.37 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.88 cm/s |
Log Po/w (iLOGP) : | 2.28 |
Log Po/w (XLOGP3) : | 2.36 |
Log Po/w (WLOGP) : | 2.13 |
Log Po/w (MLOGP) : | 1.89 |
Log Po/w (SILICOS-IT) : | 2.81 |
Consensus Log Po/w : | 2.29 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.57 |
Solubility : | 0.553 mg/ml ; 0.00268 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.91 |
Solubility : | 0.253 mg/ml ; 0.00123 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.62 |
Solubility : | 0.0489 mg/ml ; 0.000237 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.74 |
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 |
---|---|---|
77% | Stage #1: With sodium hydride In toluene; mineral oil at 20℃; for 0.25 h; Inert atmosphere Stage #2: for 18 h; Reflux; Inert atmosphere |
To a stirred suspension of sodium hydride (60percent dispersion in mineral oil, 7.20 g, 180 mmol, 3.6 equiv) in toluene (300 mL) was slowly added diethyl carbonate (23.6 g, 200 mmol, 4.0 equiv) at ambient temperature. After stirring for 15 minutes, 2-methyl acetophenone (6.70 g, 50.0 mmol, 1.0 equiv) was added, and the resultant mixture heated to reflux for 18 hours. Glacial acetic acid (15 mL) was then added drop-wise over 10 minutes, followed by the cautious addition of ice cold water (150 mL). The resultant mixture was extracted with ethyl acetate and the combined organic extracts dried over magnesium sulfate and concentrated under vacuum. The resultant residue was purified by flash column chromatography on silica gel (gradient: 0 to 5percent ethyl acetate in pentane) to afford 7.94 g (77percent) of 3-oxo-3-o-tolyl-propionic acid ethyl ester as an oil (4:1 mixture of keto/enol tautomers). 1H NMR (Keto tautomer) (400 MHz, CDCl3) δ: 7.66 (s, 1H), 7.41 (s, 1H), 7.30-7.25 (m, 2H), 4.22-4.15 (m, 2H), 3.96-3.94 (m, 2H), 2.55 (s, 3H), 1.28-1.22 (m, 3 H). |
54% | With sodium hydride In toluene; mineral oil for 16 h; Reflux | To a solution of 1-(2-methylphenyl)ethan-1-one (5 g, 37.26 mmol) in toluene (130 mL) was added diethyl carbonate (13.21 g, 111.79 mmol) andNaH (60percent, 2.98 g, 74.53 mmol). The reaction mixture was refluxed for 16 hours. After cooling, the reaction mixture was poured into ice water (200 mL) and extracted in to ethyl acetate (3 x 200 mL). The combined organic layers were dried overmagnesium sulfate, filtered and evaporated under reduced pressure to provide 9.5 g of a yellow oil. The oil was chromatographed by silica gel column chromatography (ethyl acetate in heptanes) to provide the title compound as an orange oil (6.23 g, 54percent yield). LC-MS: tRl.99 mi [M+H]207. |
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