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CAS No. : | 4934-99-0 | MDL No. : | MFCD00512755 |
Formula : | C6H10O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 130.14 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.83 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 31.29 |
TPSA : | 46.53 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.13 cm/s |
Log Po/w (iLOGP) : | 1.56 |
Log Po/w (XLOGP3) : | -0.05 |
Log Po/w (WLOGP) : | -0.07 |
Log Po/w (MLOGP) : | 0.0 |
Log Po/w (SILICOS-IT) : | 0.33 |
Consensus Log Po/w : | 0.35 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.48 |
Solubility : | 42.8 mg/ml ; 0.329 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.48 |
Solubility : | 43.4 mg/ml ; 0.334 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.01 |
Solubility : | 133.0 mg/ml ; 1.02 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.51 |
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 |
---|---|---|
88% | With lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at -78 - -60℃; for 3 h; | Methyl 3-carbonyl-cyclobutanecarboxylate (307.5 g, 2.4 mol, 1.0 eq.) was dissolved in 3 L of tetrahydrofuran and cooled to -After 78--60°C, a 3.5 L solution of lithium tri-tert-butoxyaluminum hydride (915.4 g, 3.6 mol, 1.5 eq.) in tetrahydrofuran was added dropwise.After 3h incubation, the TLC reaction was completed and 1L of 2.5mol was added dropwise.L-1 hydrochloric acid quenches the reaction and adjusts the pH of the reaction solution at 5Between ~6, and control the temperature at about 0°C, add 3L of ethyl acetate and dilute for 30 min.Pad diatomaceous earth filtration, filter cakeThe ethyl acetate was washed 3 times and the filtrate was partitioned.The aqueous phase is extracted with ethyl acetate, all organic phases are combined, dried and concentratedPale yellow liquid methyl cis-3-hydroxycyclobutylcarboxylate (273.3 g, 2.1 mol), yield 88percent, purity 95percent. |
68.5% | With sodium tetrahydroborate In methanol at 0 - 20℃; for 1 h; Inert atmosphere | Under N2 atmosphere, to a solution of methyl 3-oxocyclobutanecarboxylate (11.5 g,89.8 mmol) in MeOH (50 mL) was added sodium borohydride (3.72 g, 98.6 mmol) at 0 °C. Themixture was stirred at 0 oc for 30 min, and the reaction was allowed to warm to roomtemperature for another 30 min. The reaction mixture was quenched by the addition of thesaturated NH4Cl aqueous solution (50 mL), and then extracted with EtOAc (200 mL x 3). Thecombined organic layers were washed with brine (100mL) and dried over anhydrous Na2S04,filtered and then concentrated in vacuo. The residue was purified by silica gel columnchromatography ((PE/EtOAc (v/v) = 3/1) to give the title compound as a brown solid (8.00g,yield 68.5percent).1HNMR (400 MHz, CDCh) 8 (ppm): 4.20-4.16(m, 1H), 3.68 (s, 3H), 2.59 (t, J= 5.8 Hz, 3H),2.31 (s, 1H), 2.20-2.12 (m, 2H). |
68.5% | at 0 - 20℃; for 1 h; Inert atmosphere | In a nitrogen atmosphere,To a solution of methyl 3-oxocyclobutanecarboxylate (11.5 g, 89.8 mmol) in MeOH (50 mL) at 0 ° C was added sodium borohydride (3.72 g, 98.6 mmol).The reaction mixture was stirred at 0 & lt; 0 & gt; C for 30 min,And then moved to room temperature to continue stirring for 30 minutes.The resulting mixture was quenched by the addition of saturated aqueous ammonium chloride solution (50 mL)And then extracted with ethyl acetate (200 mL x 3).The combined organic phases were washed with saturated brine (100 mL)Then dried over anhydrous sodium sulfate,filter,The filtrate was concentrated under reduced pressure.The resulting residue was purified by silica gel column chromatography (PE / EtOAc (v / v) = 3/1)The title compound was obtained as a brown solid (8.00 g, 68.5percent yield). |
39% | With methanol; sodium tetrahydroborate In tetrahydrofuran at 0℃; for 2 h; | At 0 , the 3-oxo-cyclobutane carboxylate (8g, 62.5mmol, 1eq.) In THF / MeOH (1 / 2,240mL) was added sodium borohydride (4.75g, 125mmol, 2eq.). The reaction was stirred at 0 2h, saturated ammonium chloride solution was added 50mL, and then concentrated under reduced pressure, theThe residue was slurried with EtOAc 150mL, and then purified by silica gel column chromatography (eluent: PE / EtOAc (V / V) = 3/1) to give the title as a colorless oilCompound (3.2g, 39percent). |
39% | With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 2 h; | A solution of methyl 3-oxocyclobutanecarboxylate (8 g, 62.5 mmol) in THF / MeOH (v / v = 1/2, 240 mL) was added sodium borohydride (4.75 g, 125 mmol) at 0 ° C The temperature was continued for 2 h.After completion of the reaction, a saturated aqueous solution of ammonium chloride (50 mL) was added to the mixture, and the solvent was removed under reduced pressure to give the crude product. The crude product was beaten with ethyl acetate (150 ml) and filtered. The filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified with silica gel The title compound (3.2 g, 39percent) was purified by column chromatography (petroleum ether / ethyl acetate (v / v) = 3/1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5 h; Stage #2: With triethylamine In dichloromethane at -78 - 20℃; for 2 h; |
To a solution of oxalyl chloride (5.25 mL, 60.0 mmol) in DCM (200 ml) at -78° C. was added DMSO (7.10 mL, 100 mmol). After 30 minutes, a solution of methyl 3-hydroxycyclobutanecarboxylate (6.51 g, 50 mmol) in methylene chloride (50 mL) was added. The mixture was stirred for 30 minutes at -78° C. and TEA (27.9 mL, 200 mmol) was then added. The mixture was allowed to warm to room temperature over 2 hours. To the reaction mixture was then added water and the layers separated. The organic phase was washed with water, dried over Na2SO4 and concentrated to give product (quantitative yield). 1H NMR (400 MHz, CDCl3): 3.14-3.32 (m, 3H) 3.32-3.46 (m, 2H) 3.73 (s, 3H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; | Methyl cis-3-hydroxycyclobutylcarboxylate prepared in Example 1 (273.3 g, 2.1 mol, 1 eq.) was dissolvedIn H2O/THF (1L/1.5L),Lithium hydroxide monohydrate (218.2 g, 5.2 mol, 2.5 eq.) was then added.Stir overnight at room temperatureWhen the reaction is complete, remove THF.Adjust pH = 4 ~ 5,Then the mixture was extracted with a 4:1 volume ratio of chloroform/isopropanol.Combine the organic phase,Dry and concentrate to get crude product.The crude product was beaten with ethyl acetate/n-heptane,An off-white solid (197.4 g, 1.7 mol) was obtained,For the final product,Yield 81percent,97percent purity |
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