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CAS No. : | 72985-23-0 | MDL No. : | MFCD12547299 |
Formula : | C9H8O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YNXGZAZFHFMWPY-UHFFFAOYSA-N |
M.W : | 148.16 | Pubchem ID : | 638756 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.73 |
TPSA : | 26.3 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) : | -6.38 cm/s |
Log Po/w (iLOGP) : | 1.79 |
Log Po/w (XLOGP3) : | 1.16 |
Log Po/w (WLOGP) : | 1.51 |
Log Po/w (MLOGP) : | 1.86 |
Log Po/w (SILICOS-IT) : | 2.65 |
Consensus Log Po/w : | 1.79 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.89 |
Solubility : | 1.9 mg/ml ; 0.0128 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.31 |
Solubility : | 7.3 mg/ml ; 0.0493 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.94 |
Solubility : | 0.169 mg/ml ; 0.00114 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.64 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
96% | With calcium hydroxide In methanol | Step 4: 6-methylphthalide A total of 107 g (472 mmol) of 6-bromomethylphthalide was dissolved in 50 mL of methanol (dioxane was also used in different experiment). The solution was added to a parr bottle with 40 g (540 mmol) of calcium hydroxide and 2 g of 10percent Pd/C. The suspension was hydrogenated at 40 psi until no more hydrogen uptake was recorded. All solids were filtered and filtrate was concentrated to a total of 67 g of brown solid in 96percent yield. 1H NMR (CDCl3) (300 MHz) δ 2.53 (s, 3H), 5.30 (s, 2H), 7.49 (s 1H), 7.54 (d, 3JHCCH=7.9 Hz, 1H), 7.47 (d, 3JHCCH=7.9 Hz, 1H) |
96% | With hydrogen; calcium hydroxide In methanol | Step 4: 6-methylphthalide A total of 107 g (472 mmol) of 6-bromomethylphthalide was dissolved in 50 mL of methanol (dioxane was also used in different experiment). The solution was added to a parr bottle with 40 g (540 mmol) of calcium hydroxide and 2 g of 10percent Pd/C. The suspension was hydrogenated at 40 psi until no more hydrogen uptake was recorded. All solids were filtered and filtrate was concentrated to a total of 67 g of brown solid in 96percent yield. 1H NMR (CDCl3) (300 MHz) δ 2.53 (s, 3H), 5.30 (s, 2H), 7.49 (s 1H), 7.54 (d, 3JHCCH=7.9 Hz, 1H), 7.47 (d, 3JHCCH=7.9 Hz, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tris-(o-tolyl)phosphine In N,N,N,N,N,N-hexamethylphosphoric triamide at 50℃; for 2 h; | Tris(dibenzylideneacetone)dipalladium (0) (30 mg, 0.033 mmol), tri-o-tolylphosphine (40 mg, 0.13 mmol), and tetramethyltin (600 mg, 3.35 mmol) were dissolved in hexamethylphosphoramide (0.6 ml), and 6-bromo-1(3H)-isobenzofuranone (144 mg, 0.676 mmol) obtained from Example 26-(2) was added thereto, then the mixture was heated at 50°C for 2 hours. After cooling the reaction mixture, the mixture was diluted with ethyl acetate, and washed successively twice with water and twice with an aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was subjected to chromatography on a silica gel (5 g) column (eluent; hexane : ethyl acetate = 3 : 1). The fractions containing the target compound were concentrated, and the obtained solid was recrystallized to afford the title compound (88.3 mg, 88percent yield) as a crystalline solid. NMR spectrum (400 MHz, CDCl3) δ ppm: 2.472 (3H, s), 5.284 (2H, s), 7.376 (1H, d, J=8 Hz), 7.497 (1H, d, J=8 Hz), 7.721 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triethylamine In acetonitrile at 250℃; for 24 h; Autoclave | General procedure: A magnetic stirring bar, 2-iodobenzyl alcohol (1a, 116.0 mg, 0.5 mmol), NEt3 (251.6 mg, 2.5 mmol), and MeCN (10 mL) were placed in a stainless steel autoclave equipped with an inserted Pyrex glass liner. The autoclave was closed, purged three times with carbon monoxide, pressurized with 65 atm of CO and then heated at 250 °C by salt bath with stirring for 16 h. After the reaction, excess CO was discharged at room temperature. The solvent was removed under reduced pressure, and the residue was purified by flash chromatography on silica gel (hexane/EtOAc = 3/1) to give 2a (60.4 mg, 91percent) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With ammonium iodide; Oxone; potassium bromide In 2,2,2-trifluoroethanol; acetonitrile at 20℃; for 12 h; Green chemistry | General procedure: To a mixture of MeCN and CF3CH2OH (6:4) (5.0 mL), carboxylic acid 1 (0.5 mmol), NH4I (0.25mmol), KBr (0.4 mmol) and Oxone○® (0.75 mmol) were added. The resulting solution was stirred at room temperature for 12 h and then solvents were removed under reduced pressure. Water (10mL), sat. aq Na2S2O3 (4 mL) and sat. aq Na2CO3 (4 mL) were added to the residue and the mixture was stirred for another 5 min. The mixture was extracted with CH2Cl2 (3×10 mL) and the combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative TLC on silica gelusing (hexane-AcOEt 3:1) as eluant to give the pure product of aryl lactone 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29.9% | With calcium carbonate In 1,4-dioxane; water for 5 h; Reflux | 6. 6-Methylisobenzofuran- 1 (3H)-one; A heterogeneous, colorless solution of methyl 2-(bromomethyl)-5- methylbenzoate and regioisomer (27.2 mmol) and calcium carbonate (16.33 g, 163 mmol) in 1,4-dioxane (194 mL) and water (194 mL) was refluxed. After 5 hr, the reaction was cooled to room temperature. The insolubles were filtered, and the filtrate wasconcentrated in vacuo. The residue was extracted with CH2CL2 (2 x 200 mL). The organic layers were combined, dried over MgSO4, and concentrated in vacuo to give an oil which was purified by flash chromatography using an ISCO 220g column eluting with 10-50percent EtOAc/hexanes. Appropriate fractions were collected and concentrated in vacuo to give the desired product (1.205 g, 8.13 mmol, 29.9percent yield) as a white solid. |
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