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CAS No. : | 82578-45-8 | MDL No. : | MFCD00040559 |
Formula : | C8H16O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PKPVFILAHLKSNJ-LURJTMIESA-N |
M.W : | 160.21 | Pubchem ID : | 10154184 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.88 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.05 |
TPSA : | 46.53 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) : | -6.72 cm/s |
Log Po/w (iLOGP) : | 2.2 |
Log Po/w (XLOGP3) : | 0.78 |
Log Po/w (WLOGP) : | 1.1 |
Log Po/w (MLOGP) : | 1.08 |
Log Po/w (SILICOS-IT) : | 0.9 |
Consensus Log Po/w : | 1.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.06 |
Solubility : | 13.9 mg/ml ; 0.087 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.34 |
Solubility : | 7.36 mg/ml ; 0.0459 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.03 |
Solubility : | 14.8 mg/ml ; 0.0925 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.27 |
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 |
---|---|---|
80.3% | With Rhizopus arrhizus In ethanol; water at 24 - 25℃; for 72 h; Microbiological reaction; Enzymatic reaction | General procedure: The laboratory scale-up bioreduction of ketones 1–7 was carried out as follows. After 72h of fermentation, R. arrhizus mycelia were separated from the culture broth. The 10percent wet mycelia were put in a 1.5L sterilized fresh culture medium as working volume in 5L Erlenmeyer flask under aseptic conditions and incubated at room temperature for 72h under static conditions. After the growth of the fungus, the substrate (1g) in ethanol was added directly to the medium and then incubated at room temperature on a rotary shaker (100rpm) for 8days. At the end of the incubation period, the mycelia were separated by filtration. Mycelia was washed with water and then the combined aqueous medium was extracted with chloroform. The chloroform extract washed with water and dried over Na2SO4. After removal of the solvent under reduced pressure, the product alcohol was isolated, purified, and characterized as described earlier. The absolute configuration was determined by the sign of the specific rotation and comparison with the literature data. Isolated yield: 0.81g, [α]D26=+28.6 (c 0.483, CHCl3) >99percent ee {lit.2f=+32.3 (c 1.03, CHCl3), 99.0percent ee}; 1H NMR (CDCl3, 200MHz): δ 1.25 (d, 3H, CH3), 1.48 (s, 9H, CH3), 2.27–2.49 (m, 2H, CH2), 3.09 (s, 1H, OH),, 4.08–4.22 (m, 1H, CHOH); 13C NMR (CDCl3, 200MHz, ppm): 22.21, 27.93, 43.79, 64.18, 80.94, 172.15; methoxyl resonances of MTPA ester, 1H NMR: δ 3.55 [major, (S)-isomer] |
97 % ee | With D-Glucose In water at 30℃; for 2.73333 h; Flow reactor; Enzymatic reaction | General procedure: A solution of 5 g of glucose in 100 mL of distilled water was prepared and the β-ketoester [ethyl 3-oxohexanoate (1) or tert-butyl 3-oxobutanoate (2)] were added to the solution (0.025 mol L-1 or 4 g L-1). The starting mixture was stirred for 5 min while the instrument Asia Flow Reactor was equipped with Omnifit column (volume: 12.3 mL) containing the immobilized cells from Kluyveromyces marxianus [for the bioreduction of ethyl 3-oxohexanoate (1)] and Rhodotorula rubra [for the bioreduction of tert-butyl 3-oxobutanoate (2)]. The temperature (30 °C) was selected on the flow reactor and for each flow tested (0.2 mL min‑1, 0.1 mL min-1 and 0.075 mL min-1), first only the pure solvent (glucose 5percent) was pumped through the system. At this point, the reaction mixture [ethyl 3-oxohexanoate (1) ortert‑butyl 3-oxobutanoate (2)] was pumped through the system and aliquots were collected in different times depending on the flow rate tested (0.2 mL min-1 = 62 min; 0.1 mL min‑1 = 123 min; 0.075 mL min-1 = 164 min). The reaction mixture was extracted with ethyl acetate. The organic phase was dried (anhydrous Na2SO4), filtered, and concentrated under vacuum. Products were analyzed by (chiral) gas chromatography (GC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84 % ee | With hydrogen; acetic acid In tetrahydrofuran at 100℃; for 20 h; Autoclave | General procedure: Nickel powders (5 μm) purchased from Aldrich were directly subjected to chiral modification without any pretreatment, such as hydrogen activation. The chiral modification was performed under the conditions optimized previously for this type of catalyst.26 Thus, the non-activated nickel powders (0.5 g) were immersed in an aqueous solution (50 cm3) of (R,R)-tartaric acid (0.5g) and NaBr (2.0 g) at 100 °C, the pH of which was pre-adjusted to 3.2 with an aqueous 1M NaOH solution. NaBr was added to the modification solution to block the non-enantiodifferentiating sites of tartaric acid/Ni catalyst, thus preventing the generation of racemic products.39 After immersion for 1 h, the modification solution was removed by decantation and the catalyst was successively washed once with deionized water (10 cm3), twice with methanol (25 cm3), and twice with tetrahydrofuran (THF) (10 cm3). The modified catalyst was added to a mixture of alkyl acetoacetate (43 mmol for methyl ester and 21.5 mmol for other esters), acetic acid (0.1g), and THF (10 cm3) placed in an autoclave equipped with a magnetically coupled mechanical stirrer. The hydrogenation was run for 20h at 100 or 110 °C and at a hydrogen pressure of 9MPa. The hydrogenation product, a mixture of alkyl (R)- and (S)-3-hydroxybutyrates, was isolated from the reaction mixture by distillation. The conversion was determined by gas-liquid chromatography (GLC) on a GL Science model GC-4000 equipped with a CP Chirasil DEX-CB capillary column (0.25 mm × 25 m) at 90 °C, while the enantioselectivity was determined by chiral GLC after acetylation of the reaction product using acetyl chloride and pyridine. A portion of the acetylated sample was subjected to the chiral GLC analysis on a CP Chirasil DEX-CB column (0.25 mm × 25 m) operated at 90 °C. The ee value was calculated from the peak integration of the corresponding enantiomer peaks. The reproducibility of the ee value was found to be within ±2percent. |
89.2 % ee | With hydrogen In isopropyl alcohol at 50℃; for 10 h; Autoclave; Glovebox | General procedure: As a typical run for asymmetric hydrogenation of β-keto esters, 0.026 g Ru/5-BINAPPOPs-1 catalyst, 0.20 g methyl acetoacetate, and 2 mL of isopropanol (ipro) were added to a 30-mL autoclave in a glove box. After the reactor was purged with H2 four times, its pressure was finally adjusted to the desired value, heated from room temperature to the reaction temperature of 50 °C, and stirred for 10 h. The catalyst was separated by centrifugation, and the product was analysed using gas chromatography (GC; Agilent 7890B gas chromatograph equipped with a flame ionization detector and a Cyclosil-B capillary column). |
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