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CAS No. : | 230642-84-9 | MDL No. : | MFCD09030659 |
Formula : | C10H10O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WLZOPMPOGRQZCJ-UHFFFAOYSA-N |
M.W : | 146.19 | Pubchem ID : | 11446416 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.88 |
TPSA : | 9.23 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) : | -5.27 cm/s |
Log Po/w (iLOGP) : | 2.27 |
Log Po/w (XLOGP3) : | 2.7 |
Log Po/w (WLOGP) : | 2.16 |
Log Po/w (MLOGP) : | 2.28 |
Log Po/w (SILICOS-IT) : | 3.3 |
Consensus Log Po/w : | 2.54 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.78 |
Solubility : | 0.24 mg/ml ; 0.00164 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.55 |
Solubility : | 0.415 mg/ml ; 0.00284 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.11 |
Solubility : | 0.113 mg/ml ; 0.000773 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.9 |
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 potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; for 3.83333 h; | The Part C tosylate (100 g, 314 mmol) was dissolved in THF (1200 mL) in a 2000 mL three-neck round bottomed flask equipped with a mechanical stirrer, a digital thermometer, and a pressure equalizing addition funnel at room temperature. The reaction mixture was cooled to 0°C by an ice-water bath. To this was added a solution of t-BuOK (1 M, 345.5 mL) in THF dropwise at 0°C over a period of 110 min. The reaction mixture was warmed to ambient temperature and stirred for additional 2 hr. Water (350 mL) and EtOAc (600 mL) were added and the two layers were separated. The aqueous layer was further extracted with EtOAc (2 x 150 mL). The combined EtOAc layers were washed with brine (2 x 150 mL) dried over MgSO4 and filtered. The solvent was removed under reduced pressure to give 46 g of the title styrene in 100percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With tris-(dibenzylideneacetone)dipalladium(0); cesium fluoride; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 110℃; for 24 h; Inert atmosphere | To a solution of 4-chloro-2,3-dihydro-1- benzofuran (11.5 g, 74.39 mmol, 1.00 equiv), tri-tert-butyl(ethenyl)stannane (38.00 g, 119.48 mmol, 1.60 equiv), CsF (25 g, 164.47 mmol, 2.20 equiv), (t-Bu)3P HBF4 (1.3 g, 4.48 mmol, 0.06 equiv) in dioxane (300 mL) was added Pd2(dba)3 (1.5 g, 1.45 mmol, 0.02 equiv) under an atmosphere of nitrogen. The resulting solution was stirred for 24 h at 110 °C. The reaction progress was monitored by GCMS. The resulting solution was diluted with 300 mL of ethyl acetate. Then the solids were filtered out. The organic layers were washed with brine (2 x 300 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by 5i02 chromatography, eluted with petroleum ether to afford 5 g (46percent) of 4-ethenyl-2,3-dihydro-1-benzofuran as light yellow oil. ‘H NMR (300 MHz, CDC13) c5: 7.09-7.00 (m, 1H), 6.98-6.96 (m, 1H), 6.74-6.70 (m, 2H), 5.68 (m, 1H), 5.30 (m, 1H), 4.62-4.52 (m, 2H), 3.27-3.04 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87 %Chromat. | at 20 - 80℃; Autoclave; Inert atmosphere | Example 2 (Preparation of reaction mixture containing 4-vinyl-2,3-dihydrobenzofuran); Into a 50 mL-volume autoclave, 1.0 g (5 mmol) of 4-bromo-2,3-dihydrobenzofuran, 1.5 g of acetonitrile, 0.8 g of water and 1.02 g (010 mmol) of triethylamine were charged. The gas phase portion in the reaction vessel was made a nitrogen atmosphere, and thereafter 5.6 mg (0.026 mmol) of palladium acetate and 30.6 mg (0.1 mmol) of tri-o-tolylphosphine were added. Ethylene was added to the reaction system to pressurize up to an internal pressure of 1.3 MPa at room temperature, and the internal temperature was raised to 80°C while stirring. After the temperature was raised, the internal pressure was adjusted to 1.4 MPa, and stirring was carried out at 75 to 80°C for 8 hours while the pressure was kept. After the reaction was completed, the obtained mixture was mixed with 3.0 g of toluene and 3.0 g of water and was subjected to liquid separation treatment, and the obtained organic layer was sequentially washed with 5percent by weight of aqueous hydrochloric acid and 4percent by weight of an aqueous sodium hydrogen carbonate solution to give 3. 53 g of a brown solution. When the solution was analyzed by high performance liquid chromatography, 18.1percent by weight of 4-vinyl-2,3-dihydrobenzofuran was contained in the solution. The yield was 87percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: With osmium(VIII) oxide In tetrahydrofuran; water at 20℃; for 0.5 h; Stage #2: With sodium periodate In tetrahydrofuran; water at 20℃; for 1 h; |
To a solution of 4-ethenyl-2,3 - dihydro-1-benzofuran (5 g, 34.20 mmol, 1.00 equiv) in tetrahydrofuran (100 mL) and water (50 mL) was added 0504 (440 mg, 1.73 mmol, 0.05 equiv). The resulting solution was stirred for 30 mm at 20 °C. Then Na104 (14.7 g, 68.69 mmol, 2.00 equiv) was added. The resulting solution was allowed to react, with stirring, for an additional 1 h at room temperature. The resulting solution was diluted with 100 mL of water. Then the resulting solution was extracted with ethyl acetate (2 x 50 mL) and the organic layers combined. The resulting mixture was washed with brine (2 x 50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to afford 5 g (99percent) of 2,3-dihydro-1-benzofuran-4-carbaldehyde as light brown oil. |
69% | Stage #1: With ozone In dichloromethane Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; |
Ozone was bubbled into a stirring cold solution of (3 g, 21 mmol, prepared as described in WO 9933460) in dichloromethane (50 mL). The reaction was monitored by TLC (20:1 hexane/ethyl acetate). Upon completion of the reaction the mixture was purged with nitrogen for a few minutes followed by the addition of Hunig's base (N,N-ethyldiisopropylamine, 5.44 g, 42 mmol). Stirring was continued while the reaction warmed to RT. The reaction was washed with 0.5 N HCl, water, and then brine. The organic layer was dried over MgSO4; filtered and concentrated in vacuo. The title compound (oil, 2.10 g, 69percent yield) was isolated via silica gel using 10percent ethyl acetate in hexanes. |
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