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CAS No. : | 1192-79-6 | MDL No. : | MFCD08236773 |
Formula : | C6H7NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LFWLUDLUCDRDAF-UHFFFAOYSA-N |
M.W : | 109.13 | Pubchem ID : | 14508 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 31.15 |
TPSA : | 32.86 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) : | -6.32 cm/s |
Log Po/w (iLOGP) : | 1.27 |
Log Po/w (XLOGP3) : | 0.91 |
Log Po/w (WLOGP) : | 1.14 |
Log Po/w (MLOGP) : | -0.18 |
Log Po/w (SILICOS-IT) : | 2.0 |
Consensus Log Po/w : | 1.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.49 |
Solubility : | 3.56 mg/ml ; 0.0326 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.19 |
Solubility : | 7.12 mg/ml ; 0.0652 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.88 |
Solubility : | 1.44 mg/ml ; 0.0132 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
56% | Stage #1: With trichlorophosphate In 1,2-dichloro-ethane at 0 - 20℃; for 0.25 h; Stage #2: at 0 - 80℃; for 0.5 h; Stage #3: With water; sodium acetate In 1,2-dichloro-ethane at 80℃; for 0.333333 h; |
DMF (8.54 g, 117 mmol) and dichloroethane (120 mL) were added to a 250-mL 3-necked round-bottom flask fitted with a magnetic stir bar. Phosphoryl chloride (17.9 g, 117 mmol) was added dropwise with stirring at 0° C. The resulting solution was stirred for 15 min at room temperature and then 2-methyl-1H-pyrrole (10.0 g, 123 mmol) was added dropwise with stirring at 0° C. The resulting solution was stirred at 80° C. for 30 min. A solution of sodium acetate (46 g, 561 mmol) in water (130 mL) was then added at room temperature. The resulting solution was stirred for 20 min at 80° C. then cooled to room temperature and quenched with water (100 mL). The resulting solution was extracted with dichloromethane (3×250 mL) and the organic layers were combined and washed with saturate aqueous sodium bicarbonate solution (150 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/hexane (1:5 v/v) to afford 5-methyl-1H-pyrrole-2-carbaldehyde (7.50 g, 56percent). LCMS (ESI) m/z 110 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | Stage #1: for 0.333333 h; Stage #2: for 0.25 h; Heating / reflux Stage #3: With sodium acetate In 1,2-dichloro-ethane at 80℃; for 0.333333 h; |
B. 2-Formyl-5-methyl-pyrrole To 0.54 ml of DMF, with ice cooling and under argon, was added dropwise 0.64 ml of POCl3. The reaction, which solidified during the addition, was warmed lightly with a warm water bath and the clear colorless solution stirred an additional 20 min after addition was completed. The mixture was diluted with 3 ml of 1,2-dichloroethane and, with cooling, a solution of 510 mg (6.3 mmol) of Compound A was added dropwise. The solution was heated at reflux for 15 min, ice cooled and a solution of 2.6 g (31.5 mmol) of sodium acetate was added with vigorous stirring. The mixture was heated at 80° C. for 20 min, cooled to rt and extracted with methylene chloride. The extracts were washed with brine, dried (MgSO4) and the solvent removed to give a dark oil residue. This material was subjected to flash chromatography on silica with 10percent EtOAc:hexane to afford 126 mg (18percent) of Compound B as a light tan solid. |
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