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CAS No. : | 67751-23-9 | MDL No. : | MFCD00085024 |
Formula : | C8H15NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DFZIBCAWOSFLFR-AATRIKPKSA-N |
M.W : | 173.21 | Pubchem ID : | 5709580 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.62 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 45.36 |
TPSA : | 38.77 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) : | -7.23 cm/s |
Log Po/w (iLOGP) : | 2.29 |
Log Po/w (XLOGP3) : | 0.18 |
Log Po/w (WLOGP) : | 0.25 |
Log Po/w (MLOGP) : | -0.29 |
Log Po/w (SILICOS-IT) : | 0.05 |
Consensus Log Po/w : | 0.5 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.7 |
Solubility : | 34.8 mg/ml ; 0.201 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.55 |
Solubility : | 48.6 mg/ml ; 0.28 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.33 |
Solubility : | 81.2 mg/ml ; 0.469 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.77 |
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 |
---|---|---|
70% | With sodium hydroxide In water at 20℃; | methyl hydrazine (24 cm3, 19.5 g, 0.423 mol) was added dropwise to a solution of 17.0 g NaOH (0.423 mol) in 225 cm3 H2O upon cooling. Compound 16 (73.3 g,0.423 mol) was then added dropwise at rt, and the mixture was stirred overnight. Aq. HCl (36 percent, 28.2 g, 0.278 mol) was added upon cooling, the reaction mixture was stirred at rt for 1 h, and then extracted with CH2Cl2 (4 9 100 cm3). The combined organic phases were dried over Na2SO4, and the solvent was evaporated under reduced pressure. The residue was dissolved in 420 cm3 1 M aq. HCl and stirred at rt for 3 h. Then 10 percent aq K2CO3 was added to adjust pH = 10, and the mixture was extracted with CH2Cl2 (3 9 200 cm3). The organic layer was dried in vacuo and evaporated. The residue was distilled in vacuo to give 10a. Yield 32.8 g (70 percent); colorless liquid; b.p.: 70–72 °C (3 mbar); MS (ESI):m/z = 111 ([M+H]+); 1H NMR (500 MHz, CDCl3):d = 9.84 (s, 1H), 7.36 (d, J = 1.4 Hz, 1H), 6.68 (d,J = 1.4 Hz, 1H), 3.91 (s, 3H) ppm; 13C NMR (126 MHz,CDCl3): d = 185.8, 150.9, 131.8, 105.8, 39.2 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Stage #1: With sodium hydroxide In water at 0 - 20℃; Stage #2: With hydrogenchloride In water for 4 h; Stage #3: With sodium hydroxide In water |
12. Preparation of 1-methylpyrazole-3-carbaldehyde from 4-(dimethylamino)-1,1-dimethoxybut-3-en-2-oneWith cooling, methylhydrazine (151.3 g, 3.29 mol) was added dropwise to a solution of NaOH (131.4 g, 3.29 mol) in water (1700 ml). 4-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one (569 g, 3.28 mol) was then added dropwise at room temperature, and the mixture was stirred overnight. Hydrochloric acid (36percent strength, 219.6 g, 2.17 mol) was added, and the reaction mixture was stirred for 4 h. Using aqueous sodium hydroxide solution (10percent strength), the reaction mixture was then adjusted to a pH of 9.4. After four extractions with methylene chloride (500 ml), the organic phases were washed with water, dried over magnesium sulfate and filtered, and the solvent was removed under reduced pressure. According to GC analysis, the oily residue had a purity of 73percent. In addition to the desired 1-methylpyrazole-3-carbaldehyde, the residue contained, as a byproduct, 10.7percent of the 5-carbaldehyde. This was removed by distillation under reduced pressure (transition temperature: 55° C. at 2.5 to 2.3 mbar). The yield of 1-methylpyrazole-3-carbaldehyde was 53percent. 1H-NMR (CDCl3): δ=4.05 (s, 3H) 6.8 (s, 1H), 7.5 (s, 1H), 9.95 ppm (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Stage #1: With sodium hydroxide In water at 0 - 20℃; Stage #2: With hydrogenchloride In water for 4 h; Stage #3: With sodium hydroxide In water |
12. Preparation of 1-methylpyrazole-3-carbaldehyde from 4-(dimethylamino)-1,1-dimethoxybut-3-en-2-oneWith cooling, methylhydrazine (151.3 g, 3.29 mol) was added dropwise to a solution of NaOH (131.4 g, 3.29 mol) in water (1700 ml). 4-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one (569 g, 3.28 mol) was then added dropwise at room temperature, and the mixture was stirred overnight. Hydrochloric acid (36percent strength, 219.6 g, 2.17 mol) was added, and the reaction mixture was stirred for 4 h. Using aqueous sodium hydroxide solution (10percent strength), the reaction mixture was then adjusted to a pH of 9.4. After four extractions with methylene chloride (500 ml), the organic phases were washed with water, dried over magnesium sulfate and filtered, and the solvent was removed under reduced pressure. According to GC analysis, the oily residue had a purity of 73percent. In addition to the desired 1-methylpyrazole-3-carbaldehyde, the residue contained, as a byproduct, 10.7percent of the 5-carbaldehyde. This was removed by distillation under reduced pressure (transition temperature: 55° C. at 2.5 to 2.3 mbar). The yield of 1-methylpyrazole-3-carbaldehyde was 53percent. 1H-NMR (CDCl3): δ=4.05 (s, 3H) 6.8 (s, 1H), 7.5 (s, 1H), 9.95 ppm (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | at 110 - 120℃; for 4 h; | 4-(Dimethoxymethyl)pyrimidine (C11) A mixture of (3E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (C10) (147 g, 0.85 mol) and formamidine acetate (131 g, 1.26 mol) was heated at 110-120° C. for 4 hours. After cooling to room temperature, the reaction was poured into water (250 mL) and extracted with chloroform (5*100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Distillation of the residue under vacuum afforded the product as an oil. Yield: 84 g, 0.54 mol, 64percent. Boiling point: 45-50° C./0.2 torr. NMR data was obtained using the product of a reaction run under similar conditions. 1H NMR (400 MHz, CDCl3) δ 3.30 (s, 6H), 5.21 (s, 1H), 7.46 (dd, J=5.1, 1.4 Hz, 1H), 8.68 (d, J=5.1 Hz, 1H), 9.12 (d, J=1.4 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | at 110℃; for 3 h; | 1,1-dimethoxy-N,N-dimethylmethanamine (100 g, 839 mmol, 1.02 equiv.) and 1,1-dimethoxypropan-2-one (97 g, 821 mmol) were added and stirred at 110° C. for 3 hours. The produced methanol was removed by a Dean-Stark apparatus. After the solution was cooled to room temperature, the remaining volatile materials were removed in vacuo to provide 130 g of the crude product, (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (1) (130 g, 143 g theoretical, 91percent). LC-MS m/z 283 (M+1). Reference: WO 2006/0097341A1 (incorporated by reference), pg 67. |
68% | for 20 h; Reflux | (3E)-4-(Dimethylamino)-1,1-dimethoxybut-3-en-2-one (C10) A solution of N,N-dimethylformamide dimethyl acetal (147 g, 1.23 mol) and 1,1-dimethoxyacetone (146 g, 1.24 mol) in 2-butanol (1 L) was heated at reflux for 20 hours. After removal of solvent in vacuo, the residue was distilled under vacuum to provide the product as an oil. Yield: 145 g, 0.837 mol, 68percent. Boiling point: 132-140° C./0.15 torr. NMR and MS data were obtained using the product of a reaction run under similar conditions. LCMS m/z 174.0 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.77 (br s, 3H), 3.02 (br s, 3H), 3.30 (s, 6H), 4.47 (s, 1H), 5.23 (br d, J=12.6 Hz, 1H), 7.63 (d, J=12.6 Hz, 1H). |
68% | at 110℃; for 3 h; Inert atmosphere | A stuffed solution of 1,1-dimethoxy-N,N-dimethylmethanamine (5 g, 42 mmol) was mixed with 1,1-dimethoxypropan-2-one (4.95 g, 42 mmol) under nitrogen atmosphere. The reaction mixture was heated to 110 °C for 3 h. The methanol produced was removed by Dean-Stark apparatus. After completion the solution was cooled to rt and volatiles were removed under reduced pressure to obtain oily residue. The crude material was purified by column chromatography (60-120 silica gel, 0-5percent Methanol/DCM) to afford 2.3g of the title compound (68percent). LCMS: mlz=174 [M+1]. ‘H-NMR (400MHz, CDC13) ö: 7.6 1-7.58 (d, 1H), 5.19-5.16 (d, 1H), 4.43 (s, 1H), 3.26 (s, 6H), 3.10-3.08 (d, 3H), 2.79 (s, 3H), 1.15 (s, 6H). |
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