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CAS No. : | 26825-95-6 | MDL No. : | MFCD01838179 |
Formula : | C13H25BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QNXOHINFQALBQN-UHFFFAOYSA-N |
M.W : | 293.24 | Pubchem ID : | 11022721 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.92 |
Num. rotatable bonds : | 12 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 73.76 |
TPSA : | 26.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.29 cm/s |
Log Po/w (iLOGP) : | 3.98 |
Log Po/w (XLOGP3) : | 5.35 |
Log Po/w (WLOGP) : | 4.46 |
Log Po/w (MLOGP) : | 3.82 |
Log Po/w (SILICOS-IT) : | 4.69 |
Consensus Log Po/w : | 4.46 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.24 |
Solubility : | 0.017 mg/ml ; 0.000058 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.66 |
Solubility : | 0.000649 mg/ml ; 0.00000221 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.25 |
Solubility : | 0.00164 mg/ml ; 0.00000558 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.85 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H312-H315-H319-H332-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 |
---|---|---|
93% | for 15 h; Inert atmosphere; Reflux | Methyl 12-bromododecanoate (7) was synthesized via a standard procedure by dissolving 12-bromododecanoic acid (6) (1.0 g, 3.59 mmol) in dry MeOH (10 ml) containing concentrated H2SO4 (200 μl) under argon atmosphere and heating to reflux for 15 h. MeOH was removed under reduced pressure, the residual was diluted with EtOAc (100 ml), washed with a saturated NaHCO3 solution (3 * 20 ml) and brine (2 * 20 ml), and dried with MgSO4. The solvent was removed under reduced pressure. Chromatography on silica gel with PE/EtOAc (97.5:2.5) provided the desired ester 7 (974 mg, 3.32 mmol, 93percent) as a colorless oil. The analytical data were generally consistent with those reported previously [52–54]. TLC: Rf 0.45 (PE/EtOAc, 9:1); IR (ATR, film): 2926, 2854, 1740 (C=O), 1459, 1436, 1362, 1252, 1242, 1197, 1171, 1120, 1103, 1012, 881, 723 cm-1; 1H NMR (CDCl3): δ = 1.23-1.35 (m, 12 H, 4-H to 9-H), 1.42 (tt, J = 7.4, 7.2 Hz, 2 H, 10-H), 1.62 (tt, J = 7.6, 7.4 Hz, 2 H, 3-H), 1.85 (tt, J = 7.4, 6.9 Hz, 2 H, 11-H), 2.30 (t, J = 7.6 Hz, 2 H, 2-H), 3.41 (t, J = 6.9 Hz, 2 H, 12-H), 3.67 (s, 3 H, OCH3) ppm; 13C NMR (CDCl3): δ = 25.1 (C-3), 28.3 (C-10), 28.9, 29.3, 29.4, 29.5, 29.5, 29.6 (C-4-C-9), 33.0 (C-11), 34.2 (C-12), 34.3 (C-2), 51.6 (OCH3), 174.5 (C-1) ppm; HRMS (ESI): calcd. for [C13H26O279Br/81Br]+ ([M+H]+): 293.11107/295.10902; found: 293.11113/295.10908. |
92% | With sulfuric acid In tetrahydrofuran at 65℃; for 2 h; | To a solution of 12-bromododecanoic acid (2.5 g, 8.95 mmol) in THF (7 mL) was added methanol (7.2 mL, 179 mmol). Sulfuric acid (0.50 mL, 8.95 mmol) was added dropwise and the reaction was allowed to stir at 65 °C for two hours. The reaction mixture was washed with 5percent NaHCC and brine. The organic layer was dried over anhydrous Na2SC>4, filtered, and concentrated in vacuo. Purification by silica gel chromatography (0-20percent EtOAc/hexanes) provided methyl 12-bromododecanoate (2.40 g, 92percent). lH NMR (300 MHz, CDC13) δ: ppm 3.69 (s, 3H); 3.44 (t, 2H); 2.33 (t, 2H); 1.88 (br. m, 2H); 1.64 (br. m, 2H); 1.45 (br. m, 2H); 1.31 (br. m, 12H). |
92% | With sulfuric acid In tetrahydrofuran at 65℃; for 2 h; | Step 1 : Methyl 12-bromododecanoate Chemical Formula: Ci3H25Br02 Molecular Weight: 293.25 [00618] To a solution of 12-bromododecanoic acid (2.5 g, 8.95 mmol) in THF (7 mL) was added methanol (7.2 mL, 179 mmol). Sulfuric acid (0.50 mL, 8.95 mmol) was added dropwise and the reaction was allowed to stir at 65 °C for two hours. The reaction mixture was washed with 5percent NaHCCb and brine. The organic layer was dried over anhydrous Na2SC>4, filtered, and concentrated in vacuo. Purification by ISCO silica flash chromatography (0-20percent EtOAc/hexanes) provided methyl 12-bromododecanoate (2.40 g, 92percent). Ti-NMR (300 MHz, CDCI3) δ: ppm 3.69 (s, 3H); 3.44 (t, 2H); 2.33 (t, 2H); 1.88 (br. m, 2H); 1.64 (br. m, 2H); 1.45 (br. m, 2H); 1.31 (br. m, 12H). |
92% | With sulfuric acid In tetrahydrofuran at 65℃; for 2 h; | Nonyl 8-((2-hydroxyethyl)((9Z,12Z)-octadeca-9,12-dien-l- yl)amino)octanoate [00165] To a solution of 12-bromododecanoic acid (2.5 g, 8.95 mmol) in THF (7 mL) was added methanol (7.2 mL, 179 mmol). Sulfuric acid (0.50 mL, 8.95 mmol) was added dropwise and the reaction was allowed to stir at 65 °C for two hours. The reaction mixture was washed with 5percent NaHCCb and brine. The organic layer was dried over anhydrous Na2S04, filtered, and concentrated in vacuo. Purification by silica gel chromatography (0-20percent EtOAc/hexanes) provided methyl 12-bromododecanoate (2.40 g, 92percent). [00166] NMR (300 MHz, CDCb) δ: ppm 3.69 (s, 3H); 3.44 (t, 2H); 2.33 (t, 2H); 1.88 (br. m, 2H); 1.64 (br. m, 2H); 1.45 (br. m, 2H); 1.31 (br. m, 12H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triphenylphosphine In toluene | (1) Methyl 12-hydroxydodecanoate (2.30 g, 10.0 mmol), triphenylphosphine (3.93 g, 1.5 eq), carbon tetrabromide (4.97 g, 1.5 eq) were stirred in toluene (10 ml) at room temperature for 3 hr. The reaction solution was filtered, followed by concentration to dryness. The residue was purified by column chromatography on silica gel (toluene-ethyl acetate (99: 1)) to give 2.65 g (90percent) of methyl 12-bromododecanoate. 1H-NMR (CDCl3) δ: 1.20-1.35 (12H, m), 1.39-1.43 (2H, m), 1.56-1.63 (2H, m), 1.82-1.88 (2H, m), 2.30 (2H, t, J = 7.6 Hz), 3.41 (2H, t, J = 7.6 Hz), 3.73 (3H, s) IR (KBr): 1742 cm-1EI-MS m/z: 293 (M+) |