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CAS No. : | 143537-62-6 | MDL No. : | MFCD00171363 |
Formula : | C10H15NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YRYOXRMDHALAFL-QMMMGPOBSA-N |
M.W : | 213.23 | Pubchem ID : | 688505 |
Synonyms : |
OHHL;N-(3-Oxohexanoyl)homoserine lactone;3-O-C6-(L)-HSL;N-(β-ketocaproyl)-L-Homoserine lactone
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.7 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 52.56 |
TPSA : | 72.47 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) : | -6.99 cm/s |
Log Po/w (iLOGP) : | 1.1 |
Log Po/w (XLOGP3) : | 0.86 |
Log Po/w (WLOGP) : | 0.18 |
Log Po/w (MLOGP) : | -0.17 |
Log Po/w (SILICOS-IT) : | 1.29 |
Consensus Log Po/w : | 0.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.31 |
Solubility : | 10.5 mg/ml ; 0.0492 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.97 |
Solubility : | 2.31 mg/ml ; 0.0108 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.95 |
Solubility : | 2.41 mg/ml ; 0.0113 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.39 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P270-P280-P301+P312+P330-P305+P351+P338-P337+P313-P501 | 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 |
---|---|---|
61% | With dihydrogen peroxide; vanadia; ammonium bromide In dichloromethane; water at 0℃; for 3h; chemoselective reaction; | 3.3.3. Synthesis of α-Bromo-β-keto-AHLs 2a-f General procedure: To a stirred solution of vanadium pentoxide (1.9 mmol) in water was added 50% solution of hydrogen peroxide in water (76 mmol) at ice-bath temperature while stirring. The color changed from light orange to deep red after 25-30 min. Then, ammonium bromide (5.7 mmol) was added and the reaction mixture was stirred for another 10 min. Subsequently, β-keto-AHL 1a-f (3.8 mmol) was added in dichloromethane and the reaction mixture was then stirred further for 3 h at the same temperature. After completion of the reaction, as monitored by TLC, the mixture was extracted twice with dichloromethane (25 mL) and the organic layer was washed with saturated sodium metabisulfite solution (15 mL). Finally, it was washed with water and dried with MgSO4. The organic phase was evaporated and the crude products were purified via column chromatography on silica gel (EtOAc:petroleum ether 4:1) to yield the desired 2a-f. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium hypobromide In water; acetic acid; acetone at 0℃; for 2h; | 3.3.4. Synthesis of α,α-Dichloro-β-keto and α,α-Dibromo-β-keto-AHLs 11a-f and 3a-f General procedure: To a solution of the appropriate β-keto-AHL 1a-f (1.20 mmol) in acetone (5 mL) and glacial acetic acid (2 mL) cooled to 0 °C was added dropwise sodium hypochlorite solution (3.6 mmol). The mixture was stirred for 2 h at 0 °C, then poured into saturated Na2CO3 solution and extracted with dichloromethane. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether 2:3) to afford the dichlorinated products 11a-f. Brominations were conducted as described above using freshly prepared sodium hypobromite solution (7.2 mmol). The stock solution of sodium hypobromite was prepared by slowly adding bromine (16.6 mmol) to a solution of sodium hydroxide (50 mmol) in water (25 mL) at 0 °C. The mixture was stirred for 15 min and used immediately. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With N-iodo-succinimide at 20℃; for 3h; | 3.3.5. Synthesis of α-Iodo-β-keto-AHLs 10a-f General procedure: In a porcelain mortar 1 mmol of the appropriate β-keto-AHL 1a-f was ground for 5 min with N-iodosuccinimide (1 mmol) and the mixture was left to react at room temperature for 3 h. The formed paste was subsequently extracted with dichloromethane and the organic phase was washed with water. The collected organic phase was dried with MgSO4 and evaporated. Crude products were purified by column chromatography on silica gel (EtOAc:petroleum ether 4:1) to yield the desired α-iodo-β-keto AHLs 10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sodium hypochlorite In water; acetic acid; acetone at 0℃; for 2h; | 3.3.4. Synthesis of α,α-Dichloro-β-keto and α,α-Dibromo-β-keto-AHLs 11a-f and 3a-f General procedure: To a solution of the appropriate β-keto-AHL 1a-f (1.20 mmol) in acetone (5 mL) and glacial acetic acid (2 mL) cooled to 0 °C was added dropwise sodium hypochlorite solution (3.6 mmol). The mixture was stirred for 2 h at 0 °C, then poured into saturated Na2CO3 solution and extracted with dichloromethane. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether 2:3) to afford the dichlorinated products 11a-f. Brominations were conducted as described above using freshly prepared sodium hypobromite solution (7.2 mmol). The stock solution of sodium hypobromite was prepared by slowly adding bromine (16.6 mmol) to a solution of sodium hydroxide (50 mmol) in water (25 mL) at 0 °C. The mixture was stirred for 15 min and used immediately. |
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