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CAS No. : | 4355-31-1 | MDL No. : | MFCD00077243 |
Formula : | C8H10O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 154.16 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 37.83 |
TPSA : | 43.37 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) : | -6.54 cm/s |
Log Po/w (iLOGP) : | 1.31 |
Log Po/w (XLOGP3) : | 0.99 |
Log Po/w (WLOGP) : | 0.88 |
Log Po/w (MLOGP) : | 1.39 |
Log Po/w (SILICOS-IT) : | 1.55 |
Consensus Log Po/w : | 1.22 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.42 |
Solubility : | 5.87 mg/ml ; 0.0381 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.49 |
Solubility : | 5.0 mg/ml ; 0.0324 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.14 |
Solubility : | 11.2 mg/ml ; 0.0726 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.33 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
8.3 g | at 70℃; | A solution of <strong>[4355-31-1]3-oxabicyclo[3.3.1]nonane-2,4-dione</strong> Intermediate A3 (12.9 g, 83.8 mmol) in methanol (100 mL) was stirred at 70 C overnight. The solvent was removed to give a residue, which was purified by silica gel column chromatography (petroleum ether : ethyl acetate = 10 : ito 3 : 1) to give the title compound (8.3 g, 54 % yield) as yellow solids. ?H NIVIR (400 1VIHz, CDC13) 3.68 (s, 3H), 2.38 - 2.30 (m, 2H), 2.28 - 2.25 (m, iH), 2.05 - i.98 (m, 2H), 1.93 - i.89 (m, iH), i.62 - i.52 (m, iH), i.42 - 1.30(m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In dichloromethane; at 20℃; for 4h; | A solution of dicyclohexylcarbodiimide (200 g, 1.16 mol) in CH2Cl2 (1000 ml) was added dropwise to a suspension of compound from preparation 1 (257 g, 1.25 mol) in CH2Cl2 (550 ml), and the mixture was stirred at room temperature for 4 hours.The precipitated dicyclohexylurea was filtered and washed several times with cold CH2Cl2 (200 ml*3).The combined organic layer was concentrated to give a white solid, which was suspended in MTBE (900 ml).This solid was collected by filtration, washed with MTBE (250 ml), and dried under house vacuum to give the title compound (137 g).The filtrate was concentrated to a residue, which was suspended in MTBE (250 ml) to give another 31 g of anhydride.The total yield was 168 g (94%).m.p. 138-140 C. 1H NMR: (300 MHz, CDCl3) delta 3.06 (m, 2H), 2.25 (d, 1H), 2.11 (m, 2H), 1.65-1.86 (m, 4H), 1.40-1.60 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.7% | With toluene-4-sulfonic acid; In ethanol; at 60℃; | To a solution of compound from preparation 2 (31 g, 0.2 mol) in ethanol (anhydrous, 310 ml) was added p-toluenesulfonic acid monohydrate (1.9 g, 10 mmol, 0.05 equiv.) and triethyl orthoformate (50 ml, 0.3 mol).The reaction mixture was stirred at 60 C. overnight.The volatiles were stripped and the residue was diluted with ethyl acetate (250 ml), washed with water (120 ml) and brine (100 ml), and dried over MgSO4.After filtration and evaporation, the residue was purified by chromatography.Eluding the column with 10% ethyl acetate in hexane afforded the title compound (40 g, 87.7% yield). 1H NMR: (500 MHz, CDCl3) delta 4.11 (q, J=7.0 Hz, 4H), 2.29 (dt, 2H), 2.11 (dd, 1H), 1.97 (m, 2H), 1.98 (m, 1H), 1.53 (q, J=12.5 Hz, 2H), 1.30-1.40 (m, 2H), 1.25 (t, J=7.0 Hz, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.5% | With acetic anhydride; at 140℃; for 3h;Heating / reflux; | A suspension of <strong>[3971-31-1]1,3-cyclohexanedicarboxylic acid</strong> (490 g, 2.88 mol) in acetic anhydride (1500 ml) was heated to 140 C., refluxing for 2 hours.acetic anhydride was then removed with distillation (oil bath 180 C.).To the residue was added acetic anhydride (1000 ml) and refluxed at 140 C. for 1 hour.The acetic anhydride was removed again with distillation (under house vacuum, about 50 C.).After crystals appeared, the mixture was cooled to room temperature and MTBE (400 ml) was added.The mixture was then cooled to 0-5 C. The crystals were filtered, washed with MTBE (250 ml), and dried under house vacuum to give the title compound (382 g).The filtrate was concentrated to a residue and suspended in MTBE (100 ml) to give the second crop of the title compound (14.0 g).The total yield was 396 g (90.5%). Mp 138-140 C. 1H NMR: (300 MHz, CDCl3) delta 3.06 (m, 2H), 2.25 (d, 1H), 2.11 (m, 2H), 1.65-1.86 (m, 4H), 1.40-1.60 (m, 1H). |
In acetic anhydride; | PREPARATION v 3-Oxabicyclo[3.3.1]nonane-2,4-dione A suspension of <strong>[3971-31-1]1,3-cyclohexanedicarboxylic acid</strong> (490 g, 2.88 mol) in acetic anhydride (1500 ml) was heated to 140 C., refluxing for 2 hours. Acetic anhydride was then removed with distillation (oil bath 180 C). To the residue was added acetic anhydride (1000 ml) and refluxed at 140 C. for 1 hour. The acetic anhydride was removed again with distillation (under house vacuum, about 50 C.). After crystals appeared, the mixture was cooled to room temperature and MTBE (400 ml) was added. The mixture was then cooled to 0-5 C. The crystals were filtered, washed with MTBE (250 ml), and dried under house vacuum to give the title compound (382 g). The filtrate was concentrated to a residue and suspended in MTBE (100 ml) to give the second crop of the title compound (14.0 g). The total yield was 396 g (90.5%). Mp 138-140 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3-Oxabicyclo[3.3.1]nonane-2,4-dione A solution of dicyclohexylcarbodiimide (200 g, 1.16 mol) in CH2Cl2 (1000 ml) was added dropwise to a suspension of compound from preparation 368 (257 g, 1.25 mol) in CH2Cl2 (550 ml), and the mixture was stirred at room temperature for 4 hours. The precipitated dicyclohexylurea was filtered and washed several times with cold CH2Cl2 (200 ml*3). The combined organic layer was concentrated to give a white solid, which was suspended in MTBE (900 ml). This solid was collected by filtration, washed with MTBE (250 ml), and dried under house vacuum to give the title compound (137 g). | ||
PREPARATION b 3-Oxabicyclo[3.3.1]nonane-2,4-dione A solution of dicyclohexylcarbodiimide (200 g, 1.16 mol) in CH2Cl2 (1000 ml) was added dropwise to a suspension of compound from preparation a (257 g, 1.25 mol) in CH2Cl2 (550 ml), and the mixture was stirred at room temperature for 4 hours. The precipitated dicyclohexylurea was filtered and washed several times with cold CH2Cl2 (200 ml*3). The combined organic layer was concentrated to give a white solid, which was suspended in MTBE (900 ml). This solid was collected by filtration, washed with MTBE (250 ml), and dried under house vacuum to give the title compound (137 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.7% | With p-toluenesulfonic acid monohydrate; In ethanol; hexane; ethyl acetate; | PREPARATION c cis-1,3-Cyclohexanedicarboxylic acid diethyl ester To a solution of compound from preparation b (31 g, 0.2 mol) in ethanol (anhydrous, 310 ml) was added p-toluenesulfonic acid monohydrate (1.9 g, 10 mmol, 0.05 equiv.) and triethyl orthoformate (50 ml, 0.3 mol). The reaction mixture was stirred at 60 C. overnight. The volatiles were stripped and the residue was diluted with ethyl acetate (250 ml), washed with water (120 ml) and brine (100 ml), and dried over MgSO4. After filtration and evaporation, the residue was purified by chromatography. Eluding the column with 10% ethyl acetate in hexane afforded the title compound (40 g, 87.7% yield). 1H NMR: (500 MHz, CDCl3) delta 4.11 (q, J=7.0 Hz, 4H), 2.29 (dt, 2H), 2.11 (dd, 1H) 1.97 (m, 2H), 1.98 (m, 1 H), 1.53 (q, J=12.5 Hz, 2H), 1.30-1.40 (m, 2H), 1.25 (t, J=7.0 Hz, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 120℃; for 1.5h; | A solution of <strong>[3971-31-1]cyclohexane-1,3-dicarboxylic acid</strong> (10.0 g, 58.1 mmol) in acetic anhydride (100 mL) was stirred at 120 C for 1.5 hours. The solvent was removed togive a residue (11.8 g, crude) as yellow solids. The residue was used in the next stepwithout further purification. ?H NIVIR (400 1VIHz, DMSO-d6) 2.35 - 2.27 (m, 1H), 2.26- 2.22 (m, 1H), 1.88 - 1.85 (m, 2H), 1.82 - 1.70 (m, 4H), 1.66 - 1.60 (m, 0.5H), 1.53 -1.44 (m, 0.5H), 1.30- 1.17 (m, 1H). |
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