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CAS No. : | 243984-10-3 | MDL No. : | MFCD16039229 |
Formula : | C15H17ClFNO4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LEEIJTHMHDMWLJ-AWEZNQCLSA-N |
M.W : | 361.82 | Pubchem ID : | 11545031 |
Synonyms : |
|
Num. heavy atoms : | 23 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 86.83 |
TPSA : | 80.85 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.38 cm/s |
Log Po/w (iLOGP) : | 2.71 |
Log Po/w (XLOGP3) : | 2.99 |
Log Po/w (WLOGP) : | 4.57 |
Log Po/w (MLOGP) : | 2.44 |
Log Po/w (SILICOS-IT) : | 2.58 |
Consensus Log Po/w : | 3.06 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.76 |
Solubility : | 0.0623 mg/ml ; 0.000172 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.35 |
Solubility : | 0.0161 mg/ml ; 0.0000445 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.89 |
Solubility : | 0.00465 mg/ml ; 0.0000129 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.9 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P270-P301+P312-P330 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-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 |
---|---|---|
With triethylamine; In ethyl acetate; for 14.5h; | A solution of ethyl 2-(chlorosulfonyl)cyclohex-l-enecarboxylate (3 g, 11.88 mmol) in ethyl acetate (20 mL) was added dropwise over 30 min to a solution of 2-chloro-4-fluoroaniline (2.07 g, 14.25 mmol) and Et3N (2.99 g, 29.70 mmol) in ethyl acetate (20 mL) at 0 0C under nitrogen and the mixture was stirred for 14 hours. Standard extractive work up gave a crude residue which was purified by silica gel column chromatography (8% ethyl acetate in petroleum ether), followed by trituration with hexane to give an off-white solid (0.6 g, 14%). Preparative HPLC (CHIRALPAK AD-H, 4.6 x 250 mm, hexane/ethanol (9:1), 1.0 ml/min) gave the S-enantiomer at 10.27 min and the R- enantiomer at 11.70 min. These were further purified by silica gel column chromatography (8% ethyl acetate in petroleum ether) to give the title compounds (i?-enantiomer: 30 mg; S- enantiomer: 38 mg) as off-white solids.[00274] (i?)-Ethyl 6-(lambda/-(2-chloro-4-fluorophenyl)sulfamoyl)cvclohex- 1 -enecarboxylate: m.p. 47-49 0C; MD20 +106.1 (c 1.0, methanol); 1H NMR (400 MHz, DMSO-d6) delta 1.04 (t, J = 6.3 Hz, 3H), 1.58-1.80 (m, 2H), 2.01-2.43 (m, 4H), 3.99 (q, J= 6.6 Hz, 2H), 4.27-4.32 (m, IH), 7.09 (s, IH), 7.20-7.59 (m, 3H), 9.74 (s, IH, exchangeable with D2O); IR (KBr) upsilon 3239, 2985, 2944, 1704, 1498, 1333, 1256, 1148 cm"1.(S)-Ethyl 6-(A/-(2-chloro-4-fluorophenyl)sulfamoyl)cyclohex-l -enecarboxylate: m.p. 47-49 C; HD20 -104.3 (c 1.0, methanol); 1H NMR (400 MHz, DMSO-d6) delta 1.05 (t, J = 7.0 Hz, 3H), 1.58-1.80 (m, 2H), 2.01-2.45 (m, 4H), 3.99 (q, J = 7.1 Hz, 2H), 4.28-4.32 (m, IH), 7.09 (s, IH), 7.22-7.58 (m, 3H), 9.74 (s, IH, exchangeable with D2O); IR (KBr) upsilon 3238, 2986, 2943, 1704, 1498, 1332, 1255, 1148 cm"1. |