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CAS No. : | 14205-39-1 | MDL No. : | MFCD00008072 |
Formula : | C5H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 115.13 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 29.67 |
TPSA : | 52.32 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) : | -6.58 cm/s |
Log Po/w (iLOGP) : | 1.58 |
Log Po/w (XLOGP3) : | 0.6 |
Log Po/w (WLOGP) : | 0.02 |
Log Po/w (MLOGP) : | -0.09 |
Log Po/w (SILICOS-IT) : | -0.39 |
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) : | -0.8 |
Solubility : | 18.3 mg/ml ; 0.159 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.27 |
Solubility : | 6.15 mg/ml ; 0.0534 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.02 |
Solubility : | 110.0 mg/ml ; 0.957 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | 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 |
---|---|---|
77% | With graphite oxide In neat (no solvent) at 80℃; for 2 h; | General procedure: A mixture of aldehyde 1a–1j (1 mmol), methyl 3-aminocrotonate(5 mmol), and amount of GO (as indicated inTable 2) was stirred in reflux of solvent under ambient airfor indicated time in Table 2. After completion of thereaction, the residue was dissolved in CH2Cl2 and filteredthrough a sintered funnel. The filtrate was evaporated andpurified by recrystallization from EtOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With graphite oxide In water for 7 h; Reflux | General procedure: A mixture of aldehyde 1a–1j (1 mmol), methyl 3-aminocrotonate(5 mmol), and amount of GO (as indicated inTable 2) was stirred in reflux of solvent under ambient airfor indicated time in Table 2. After completion of thereaction, the residue was dissolved in CH2Cl2 and filteredthrough a sintered funnel. The filtrate was evaporated andpurified by recrystallization from EtOH |
55% | With graphite oxide In water for 7 h; Reflux | General procedure: A mixture of aldehyde 1a–1j (1 mmol), methyl 3-aminocrotonate(5 mmol), and amount of GO (as indicated inTable 2) was stirred in reflux of solvent under ambient airfor indicated time in Table 2. After completion of thereaction, the residue was dissolved in CH2Cl2 and filteredthrough a sintered funnel. The filtrate was evaporated andpurified by recrystallization from EtOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With ammonia In methanol at 0 - 10℃; for 4 h; Large scale | 25kg of methyl acetoacetate and 20kg of methanol were pumped into the ammoniation reaction tank.The internal temperature was controlled to 0 to 10 ° C with iced water, stirred, and ammonia gas was introduced, and white crystals were precipitated, and the ammonia was stopped after 4 hours.After freezing overnight, the mixture was centrifuged to obtain white crystals, which was placed in an ammoniated refining tank, and 15 kg of methanol for purification was added thereto, and the mixture was heated to dissolve, and then freeze-crystallized at 0 to -10 ° C for 20 to 24 hours.The mixture was centrifuged and filtered, and the filter cake was dried in a hot air circulating oven at 50 to 60 ° C for 8 hours to obtain methyl 3-aminocrotonate of 18.6 to 21 kg, and the weight yield range was 74.4 to 84.0percent, and the molar yield range was 75.0 to 85.0percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With polyphosphoric acid In ethanolReflux; Inert atmosphere | General procedure: A solution of ethyl acetoacetate (3) (576 mg, 4.4 mmol),4-fluoro benzaldehyde (1a) (500 mg, 4 mmol) and thiourea(2) (306 mg, 4 mmol) in ethanol (5 mL) was heated under reflux (78-80 °C) in the presence of poly phosphoric acid(1350 mg, 4 mmol) for 12 h under nitrogen. The progress ofthe reaction was monitored by TLC (hexane: ethyl acetate,1:1 v/v). The reaction mixture, after being concentrated under vacuum at 60 °C, cooled to room temperature, it was poured into crushed ice (10 g) and stirred for 5-10 min. The solid separated was then filtered under suction, washed withice-cold water (20 mL) and then recrystallized from hot ethanol to afford pure product 4a (2.08 g, 88percent). The same experimental procedure was adopted for the preparation of remaining title compounds (4b-l & 9) (Scheme 1 & 2, Table3). |
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