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CAS No. : | 10601-80-6 | MDL No. : | MFCD00009865 |
Formula : | C9H18O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SIALOQYKFQEKOG-UHFFFAOYSA-N |
M.W : | 190.24 | Pubchem ID : | 66389 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.89 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.83 |
TPSA : | 44.76 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) : | -6.74 cm/s |
Log Po/w (iLOGP) : | 2.89 |
Log Po/w (XLOGP3) : | 1.02 |
Log Po/w (WLOGP) : | 1.34 |
Log Po/w (MLOGP) : | 0.95 |
Log Po/w (SILICOS-IT) : | 1.41 |
Consensus Log Po/w : | 1.52 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.13 |
Solubility : | 14.0 mg/ml ; 0.0734 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.55 |
Solubility : | 5.37 mg/ml ; 0.0282 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.88 |
Solubility : | 2.5 mg/ml ; 0.0131 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.41 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P370+P378-P362+P364-P403+P233-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335-H227 | 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 |
---|---|---|
92% | Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 10 - 20℃; for 1 h; Stage #2: With water In tetrahydrofuran for 2 h; |
In the following, tetrahydrofuran (THF) to be used was dehydrated on molecular sieves of 4 angstrom overnight. Inside of a 5 L four-neck flask was substituted with nitrogen gas and 2.2 kg of THF was placed therein, followed by cooling to 10° C. or lower. Then, 50 g of lithium aluminum hydride was placed therein and 250 g of ethyl 3,3-diethoxypropionate was added dropwise so that inner temperature did not exceed 10° C. After completion of the dropwise addition, temperature was elevated to 20° C. and reaction was carried out for 1 hour. After the reaction, 420 g of distilled water was added and the whole was stirred for 2 hours, then filtration was performed through No. 2 filtration paper, and subsequently a cake was washed with 1.1 kg of THF. The filtrate was concentrated at 40° C. to obtain 213 g of crude 3,3-diethoxy-1-propanol (hereinafter 33DEP).Then, 200 g of crude 33DEP was placed in a 5 L four-neck flask and 1 kg of hexane was added thereto, followed by stirring for 1 hour (step (A)). After 1 kg of a 0.1M phosphate buffer (pH 7.5) was added and the whole was stirred for 20 minutes, it was transferred to a 5 L separatory funnel and allowed to stand until it was separated into layers. After an aqueous layer was taken out, a hexane layer was returned to the 5 L four-neck flask and 1 kg of the 0.1M phosphate buffer (pH 7.5) was again added. After stirring for 20 minutes, the whole was again transferred to the 5 L separatory funnel and allowed to stand until it was separated into layers and then an aqueous layer was recovered. The aqueous layer was recovered into the 5 L four-neck flask (step (B)). Then, 2 kg of chloroform was added thereto and, after stirring for 30 minutes, the whole was transferred to the 5 L separatory funnel and allowed to stand for 15 minutes to separate it into layers. A chloroform layer was recovered and an aqueous layer was returned to the 5 L four-neck flask and the same operations were performed with 2 kg of chloroform to recover a chloroform layer (step (C)). Then, the recovered chloroform layer was concentrated at 40° C. using an evaporator and, after evaporation ceased, the solvent was evaporated by bubbling with a minute amount of nitrogen. Thereafter, the product was stirred with 20 g of molecular sieves of 4 angstrom for 5 hours and then filtration was performed to obtain 188 g of 33DEP.Then, 150 g of 33DEP obtained by the above operations was placed in a 300 ml four-neck flask and distillation was started under reduced pressure. A first fraction begun to be distilled at a degree of vacuum of 0.4 kPa, a bath temperature of 38° C., an inner temperature of 36° C., and a column top temperature of 33° C. After the distillation ceased, the bath temperature was gradually elevated and a main fraction begun to be distilled at a degree of vacuum of 0.2 kPa, a bath temperature of 58° C., an inner temperature of 55° C., and a column top temperature of 54° C. Thereafter, distillation was performed so that the column top temperature did not exceed 60° C. to obtain 138 g of the main fraction (step (D)). GC analysis was performed for the obtained main fraction. Results are shown in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydride In diethyl ether at 0 - 20℃; for 15 h; | 12.6 g of sodium hydride (purity: 60percent, 525.0 mmoles) was washed with diethyl ether by decantation several times and then made into a solution in 500 ml of diethyl ether. Thereto were added, in a nitrogen current at 0 to 10°C, 194 g (2.6 moles) of ethyl formate and 50 g (262.0 mmoles) of ethyl 3,3-diethoxy-propionate. The resulting mixture was stirred at room temperature for 15 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by washing with diethyl ether. The resulting aqueous layer was allowed to have a pH of 1 with hydrochloric acid, followed by extraction with dichloromethane. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 37.6 g (yield: 100percent) of crude (ethoxycarbonyl)malondialdehyde as a dark red oily substance. 1H-NMR [CDCl3/TMS, δ (ppm)]: 9.09 (2H,s), 5.26 (1H,s), 4.27 (2H,q), 1.28 (3H,t) |
100% | With sodium hydride In diethyl ether at 0 - 20℃; for 15 h; | REFERENCE EXAMPLE 28 Production of (ethoxycarbonyl)malondialdehyde; 12.6 g of sodium hydride (purity: 60percent, 525.0 mmoles) was washed with diethyl ether by decantation several times and then made into a solution in 500 ml of diethyl ether. Thereto were added, in a nitrogen current at 0 to 10° C., 194 g (2.6 moles) of ethyl formate and 50 g (262.0 mmoles) of ethyl 3,3-diethoxy-propionate. The resulting mixture was stirred at room temperature for 15 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by washing with diethyl ether. The resulting aqueous layer was allowed to have a pH of 1 with hydrochloric acid, followed by extraction with dichloromethane. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 37.6 g (yield: 100percent) of crude (ethoxycarbonyl)malondialdehyde as a dark red oily substance. 1H-NMR [CDCl3/TMS, δ (ppm)]: 9.09 (2H,s), 5.26 (1H,s), 4.27 (2H,q), 1.28 (3H,t) |
99.7% | With sodium hydride In tetrahydrofuran at 0 - 20℃; | [00442] To a stirred suspension of sodium hydride (60percent, 1.68 g, 42.1 mmol) in THF (20 mL) was added ethyl formate (8.5 mL, 105.7 mmol). The solution was cooled to 0 °C and a solution of ethyl 3,3-diethoxypropanoate (4 g, 21.0 mmol) in THF (10 mL) was added dropwise over 30 mins and the reaction mixture stirred at r.t. overnight. 2M aq HCl (30 mL) was added under whilst cooling with ice and the reaction stirred at r.t. for 30 mins. The reaction mixture was extracted with diethyl ether (2 x 50 mL) and the combined organic extracts were dried over MgS04 and concentrated in vacuo to afford the title compound (3.02 g, 99.7percent) as an amber liquid. [00443] 1H NMR (250 MHz, Chloroform-d) δ 9.13 (s, 2H), 4.29 (q, J = 7.1 Hz, 2H), 1.37 - 1.28 (m, 3H). |
74.2% | With sodium hydride In diethyl ether; hexane at 20℃; for 15 h; Cooling with ice | Weighed out sodium hydride (2.46 g, 61.5 mmol) in a dry 100-mL pear flask. Washed with hexanes then with diethyl ether. Suspended in ether (100 mL), cooled in ice bath then ethyl formate (24.84 ml, 308 mmol) was added then ethyl 3,3-diethoxypropanoate (5.98 ml, 30.8 mmol). The resulting mixture was stirred at room temperature for 15 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by washing with diethyl ether. The resulting aqueous layer was allowed to have a pH of 1 with hydrochloric acid, followed by extraction with dichloromethane. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate, filtered and concentrated to give ethyl 2-formyl-3-oxopropanoate (3.29 g, 22.83 mmol, 74.2 percent yield) as a golden syrup |
70% | Stage #1: With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: With hydrogenchloride In water |
EXAMPLE 1Preparation of Ethyl-2-formyl-3-oxopropionate[0059] A three- or four-neck round bottom flask equipped with magnetic stir bar, thermocouple, digital thermometer, gas inlet and outlet and addition funnel was flushed <n="19"/>with argon. Ethyl 3,3-diethoxypropionate (64.5 g) in tetrahydrofuran were charged to the addition funnel. Sodium hydride (21.2 g of a 60percent dispersion) was charged to the reaction flask followed by tetrahydrofuran. The contents of the flask were cooled to 0- 5°C in an ice-bath, and ethyl formate (257 g) was added. The mixture was cooled to 0- 50C and the contents of the addition funnel added drop wise, maintaining an internal temperature of less than 5°C. The ice-bath was removed and the contents allowed to warm to ambient temperature. Consumption of ethyl 3,3-diethoxypropionate was monitored by TLC analysis. The reaction was quenched by addition of ice-water (10.6 vol), and extracted three times with methyl t-butyl ether (5.4 vol each), and the organic layers discarded. The aqueous phase was acidified with cone, hydrochloric acid to a pH of 1 to 1.5. The acidified aqueous layer was extracted three times with dichloromethane and the combined organic layers dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue distilled under vacuum, to provide ethyl 2-formyl-3-oxopropionate, 27.92 g, 70percent yield. |
70% | With sodium hydride In tetrahydrofuran at 0 - 20℃; | [0066] A three- or four-neck round bottom flask equipped with magnetic stir bar, thermocouple, digital thermometer, gas inlet and outlet and addition funnel was flushed with argon. Ethyl 3,3- diethoxypropionate (64.5 g) in tetrahydrofuran were charged to the addition funnel. Sodium hydride (21.2 g of a 60percent dispersion) was charged to the reaction flask followed by tetrahydrofuran. The contents of the flask were cooled to 0-50C in an ice-bath, and ethyl formate (257 g) was added. The mixture was cooled to 0-50C and the contents of the addition funnel added dropwise, maintaining an internal temperature of less than 5°C. The ice-bath was removed and the contents allowed to warm to ambient temperature. Consumption of ethyl 3,3- diethoxypropionate was monitored by TLC analysis. The reaction was quenched by addition of ice-water (10.6 vol), and extracted three times with methyl t-butyl ether (5.4 vol each), and the organic layers discarded. The aqueous phase was acidified with cone, hydrochloric acid to a pH of 1 to 1.5. The acidified aqueous layer was extracted three times with dichloromethane and the combined organic layers dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue distilled under vacuum, to provide ethyl 2-formyl-3 -oxopropionate, 27.92 g, 70percent yield. |
59% | With sodium hydride In tetrahydrofuran at 0 - 30℃; for 24 h; | 4) In a 500 ml four-necked flask equipped with magnetic stirring, 160 ml of tetrahydrofuran and9.84g NaH, mass fraction of NaH in tetrahydrofuran solution is 60percent, the solution is cooled in an ice bath to 0 °C to 5 °C, and then 119g of ethyl formate is added to slowly increase the temperature, when the temperature stabilizes to 0 °C At 5 °C, 80 ml of a tetrahydrofuran solution containing D was continuously added dropwise into a 500 ml four-necked flask, wherein the mass fraction of D was 5percent. After the dropwise addition, the water bath was removed and heated to room temperature. At this time, a large amount of hydrogen was evolved. It will first rise to 30 °C and then gradually decrease to 25 °C. After 24 hours of reaction, the reaction solution was poured into ice water and quenched. 5) The resulting product is first extracted with 500 ml of tert-butyl methyl ether three times to remove the organic phase, and then with concentrated hydrochloric acid to adjust the pH of the aqueous phase to 1~1.5; then extract the aqueous phase with 300 ml of dichloromethane, twice The combined organic phases were combined; the combined organic phases were then dried over anhydrous sodium sulfate and evaporated to give a brown-red liquid which was evaporated in vacuo. GC yield was 99.3percent. The yield was 85.9percent. Finally, the 9 mm Hg diaphragm was distilled under reduced pressure. The colorless transparent liquid E, ethyl 2-formyl-3-oxopropanoate, was obtained in a yield of 59percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With tin(II) chloride dihdyrate In ethanol at 20 - 90℃; | Step 1: ethyl 6-bromoquinoline-3-carboxylate To a solution of 5-bromo-2-nitrobenzaldehyde (2 g, 9 mmol) in ethanol (46 mL) was added tin(II) chloride dihydrate (7.95 g, 35.2 mmol) and 3,3-diethoxypropionic acid ethyl ester (4.2 mL, 22 mmol). The reaction was heated to 90° C. for 16 hours. The reaction was then allowed to cool to room temperature and stir overnight. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The mixture was poured into saturated aqueous sodium bicarbonate. The resulting emulsion was filtered through Celite, rinsing with ethyl acetate. The layers were separated and the aqueous was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-50percent ethyl acetate/heptanes) gave the title compound (1.41 g, 60percent) as a solid. |
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