Structure of 69917-80-2
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CAS No. : | 69917-80-2 |
Formula : | C8H11NO2 |
M.W : | 153.18 |
SMILES Code : | O=C(OC)CCC1=CC=CN1 |
MDL No. : | MFCD09841003 |
InChI Key : | UBOXXEGSGUIRAJ-UHFFFAOYSA-N |
Pubchem ID : | 14668764 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 5 |
Fraction Csp3 | 0.38 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 41.46 |
TPSA ? Topological Polar Surface Area: Calculated from |
42.09 ?2 |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.77 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.83 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.12 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.44 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.88 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.21 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.38 |
Solubility | 6.31 mg/ml ; 0.0412 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.3 |
Solubility | 7.74 mg/ml ; 0.0505 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.48 |
Solubility | 0.511 mg/ml ; 0.00333 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.65 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.51 |
* 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 |
---|---|---|
82% | With palladium on activated charcoal; hydrogen; In methanol; | (0071) The BODIPY acid 11, used for preparing the azole fluorescent probes, was synthesized depicted in Scheme 2, following the procedure disclosed in Vanessa Saura et al. (2017). |
5 g | With palladium 10% on activated carbon; hydrogen; In methanol; at 18℃; under 2585.81 Torr; for 10h;Inert atmosphere; | [0278] To a solution of compound 15.6 (8.60 g, 56.89 mmol, 1.00 eq) m MeOH (100.00 mL) was added Pd-C (10%, 0.9 g) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 (50psi) at 18C for 10 hours. The reaction mixture was filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (S1O2, petroleum ether/ethyl acetate=5: l) to afford compound 15.5 (5.00 g, 32.64 mmol, 57.37% yield) as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.10 g (82%) | The reaction mixture was filtered through a diatomaceous earth pad and the filtrate was concentrated under vacuum to give 5.10 g (82%) of compound 31 as a pale yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The 2,2'-bipyrrole is prepared as described in Rappaport et al., J. AM. CHEM. SOC., 84, 2178 (1962). The 2-(2-methoxycarbonylethyl)-5-formylpyrrole is prepared from 2-(2-methoxycarbonylethyl)pyrrole by the Vilsmeier-Haack formylation according to ORG. SYNTH. COLL. Vol. IV, p 831. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.05% | [0279] To a mixture of compound 15.5 (3.00 g, 19.58 mmol, 1 .00 eq) and compound 15.4 (2.65 g, 21.54 mmol, 1.10 eq) in DCM (60.00 mL) was added PGCL (3.30 g, 21.54 mmol, 2.00 iriL, 1.10 eq) in one portion at 18C under N2. The mixture was stirred at 18 C for 10 hours, followed by addition of BF3 Et20 (1 1.12 g, 78.32 mmol, 9.67 mL, 4.00 eq) and DIEA (10.63 g, 82.24 mmol, 14.36 mL, 4.20 eq) dropwise at 18 C. The mixture was stirred at 18 C for 10 hours. The reaction mixture was filtered, diluted with H20 (50 mL), and extracted with DCM (3 x 50 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (S1O2, petroleum ether/ethyl acetate=l :4) to afford compound 15.3 (3.00 g, 9.80 mmol, 50.05% yield) as a red solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With palladium on activated charcoal; hydrogen; In methanol; at 20℃; for 16h; | A solution of (E)-methyl 3-(1H-pyrrol-2-yl)acrylate 3 (3.15g, 21.1mmol) in MeOH (160mL) was placed under at atmosphere of argon. Pd/C (246mg, 10%) was added, followed by replacement of the argon with a hydrogen atmosphere. The reaction was then stirred at rt until completion as indicated by TLC analysis (16h). The crude mixture was filtered over a bed of Celite, and the Celite plug was eluted a further aliquot of MeOH (50mL). The combined MeOH washes were then concentrated in vacuo to afford ester 4 (3.13g, 100%) as a pale yellow oil, which required no further purification. The NMR data obtained for ester 4 is in accordance with the literature. 1H NMR (CDCl3, 400MHz) delta: 8.53 (1H, br s), 6.69-6.68 (1H, m), 6.13-6.10 (1H, m), 5.94-5.93 (1H, m), 3.71 (3H, s), 2.93 (2H, t, J=6.6Hz), 2.66 (2H, t, J=6.6Hz). 13C NMR (CDCl3, 100MHz) delta: 174.5, 130.9, 116.8, 108.0, 105.5, 51.8, 34.4, 22.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid; In dichloromethane; at 20℃; for 24h;Inert atmosphere; | Methyl 3-(1H-pyrrol-2-yl)propanoate 2b (250 mg, 1.6 mmol) and 4-diethylamino-benzaldehyde 3b (145 mg, 0.8 mmol) were dissolved in 150 mL dry CH2Cl2 (argon was bubbled through CH2Cl2 for 30 min) under argon atmosphere. One drop of TFA was added and the reaction mixture was stirred at room temperature for 24 h under argon. p-Chloranil (202 mg, 0.8 mmol) was added and stirring was continued for 30 min under argon. Then, triethylamine (2.0 mL) and BF3*OEt2 (2.0 mL) were added, and the reaction mixture was stirred at room temperature overnight under argon. The reaction mixture was washed with H2O (40 mL), brine (40 mL), dried over Na2SO4, filtered, and evaporated. The crude mixture was purified by column chromatography on SiO2 (Hexane: EtOAc = 6:1 ~ 3:1) to afford 4d (222 mg, 0.43 mmol, 53% yield) as a red solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20℃;Inert atmosphere; | A 0C solution of <strong>[69917-80-2]methyl 3-(1H-pyrrol-2-yl)propanoate</strong> 4 (2.64g, 17.5mmol) in Et2O (130mL) was treated by the slow addition of LiAlH4 (996mg, 26.3mmol). The resulting suspension was allowed to warm up to rt and stirred until completion as indicated by TLC analysis (16h). The reaction mixture was then quenched with the dropwise addition of 1M aq NaOH until pH neutral. The Et2O layer was decanted off, and the remaining aluminium salts were washed with Et2O (3×50mL). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo to yield alcohol 5 (2.15g, quant.) as a clear oil, which required no further purification. 1H NMR (CDCl3, 400MHz) delta: 8.24 (1H, br s), 6.70-6.68 (1H, m), 6.15-6.13 (1H, m), 5.95-5.94 (1H, m), 3.73 (2H, t, J=5.9Hz), 2.75 (2H, t, J=7.3Hz), 2.72 (1H, br), 1.93-1.87 (2H, m). 13C NMR (CDCl3, 100MHz) delta: 131.8, 116.4, 108.3, 105.2, 62.3, 32.2, 24.2. The NMR data is in accordance with the literature.8 |
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