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CAS No. : | 14273-90-6 | MDL No. : | MFCD00187528 |
Formula : | C7H13BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KYLVAMSNNZMHSX-UHFFFAOYSA-N |
M.W : | 209.08 | Pubchem ID : | 4170292 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.86 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.92 |
TPSA : | 26.3 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) : | -6.24 cm/s |
Log Po/w (iLOGP) : | 2.57 |
Log Po/w (XLOGP3) : | 1.88 |
Log Po/w (WLOGP) : | 2.11 |
Log Po/w (MLOGP) : | 2.12 |
Log Po/w (SILICOS-IT) : | 2.14 |
Consensus Log Po/w : | 2.16 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.92 |
Solubility : | 2.49 mg/ml ; 0.0119 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.05 |
Solubility : | 1.84 mg/ml ; 0.00882 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.84 |
Solubility : | 0.303 mg/ml ; 0.00145 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.2 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-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 |
---|---|---|
90% | With hydrogen chloride (gas) In methanol | 1. Preparation of methyl 6-bromocaproate (methyl 6-bromohe:Kanoate). Hydrogen chloride (gas) was added to a solution of 5.01 g (25.7 mmol) of 6-bromocaproic acid in 250 ml of methanol via vigorous bubbling for 2-3 minutes. The mixture was stirred at 15-25° C. for 3 hours and then concentrated to afford 4.84 g of the product as a yellow oil (90percent): H-NMR (DMSO) 3.58 (3H, s), 3.51 (2H, t), 2.29 (2H, t), 1.78 (2H, pentet), and 1.62-1.27 ppm (4H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Heating / reflux | To a solution 6-bromohexanoic acid (10 g, 50 mmol) in MeOH was added few drops of concentrated H2SO4. The mixture was then refluxed overnight. Methanol was EPO <DP n="83"/>evaporated and the residue was taken in dichloromethane and washed with saturated solution of sodium bicarbonate and dried over MgSO4. The solvent was then evaporated to give the desired ester (10.7 g) as slightly yellow oil in quantitative yield. 1H NMR: (CDCI3) δ (ppm): 3.6 (s, 3H); 3.3 (m, 2H); 2.4 (m, 2H); 1.5-1.8 (m, 4H); 1.3 (m, 2H). |
100% | at 20℃; Cooling with ice | Synthesis of Methyl 6-bromohexanoate [0064] Add 6-bromohexanoic acid (4.1 g, 21.1 mmol) into 100 mL absolute methanol solution and then slowly drop 30 mL thionyl chloride into the solution with an ice bath. Stir the solution at room temperature overnight, concentrate the solution and add chloroform to dissolve. After suction filtration, take and concentrate the filtrate to get the product methyl 6-bromohexanoate (4.4 g, 100percent). Compound Data of the Product: [0065] IR (neat) v 11739 (CO) cm−1. [0066] 1H NMR (CDCl3) δ 3.64 (s, 3H, OCH3), 3.38 (t, 2H, BrCH2), 2.30 (t, 2H, CH2COOCH3), 1.82 (m, 2H, CH2CH2CH2CH2CH2), 1.63 (m, 2H, CH2CH2CH2CH2CH2), 1.46 (m, 2H, CH2CH2CH2CH2CH2). [0067] 13C NMR (CDCl3) δ 173.77 (CO), 51.73 (COOCH3), 33.72 (BrCH2), 33.34 (CH2CH2CH2CH2CH2), 32.30 (CH2CH2 CH2CH2CH2), 27.56 (CH2CH2CH2CH2CH2), 23.98 (CH2CH2CH2CH2CH2). |
96% | at 0 - 20℃; for 24 h; Inert atmosphere | To a stirred solution of 6-bromohexanoic acid 24 (5.00 g, 25.6 mmol) in methanol (75 mL) at 0 °C, thionyl chloride (1.86 mL, 25.6 mmol) was added dropwise. The mixture was warmed to room temperature and stirred for 24 h. The solvent wasremoved in vacuo and the residue was dissolved in ethyl acetate (20 mL), washedwith water (2 x 10 mL), sat. NaHCO3 (10 mL), brine (10 mL) and dried (MgSO4).The solvent was removed in vacuo to give the title product 23 (5.13 g, 96°h) as ayellow oil which was used without further purification. 1H NMR (300 MHz; CDCI3)1.42-1.52 (2H, m, CH2), 1.56-1.66 (2H, m, CH2), 1.85-1.90 (2H, m, CH2), 2.33(2H, t, J = 3.0 Hz, CH2), 3.41 (2H, t, J = 6.0 Hz, CH2), 3.67 (3H, s, CH3). The 1H values are in agreement with literature.5 |
96% | for 2 h; Heating / reflux | 6-Bromohexanoic acid methyl ester (27a). To a solution of acetyl chloride (1. 0 mL, 14 mmol) in methanol (150 mL) at 0°C was added a solution of 6-bromohexanoic acid (10.0 g, 51 mmol) in methanol (50 mL). The mixture was heated at reflux for 2 hours, then allowed to cool down to room temperature and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 mL) and washed consecutively with saturated aqueous sodium hydrogen carbonate (2 x 50 mL), distilled water (50 mL), and brine (50 mL). The organic layer was dried over anhydrous MgS04, filtered and concentrated under reduced pressure to give the title compound (10.3 g, 96percent) as a colourless oil. |
93% | for 8 h; Reflux | 6-bromohexanoic acid 18 (4.886 g, 25.100 mmol) was dissolvedin methanol (75 mL). To this solution, Conc. H2SO4 (0.3 mL) was added and reaction mixture refluxed for 8 h. Then solvent evaporatedand residue was dissolved in ethyl acetate (200 mL). Theorganic part was then washed with saturated solution of NaHCO3(50 mL 3), dried and evaporated to give pure ester compound(4.626 g, 22.200 mmol). For making Wittig salt, bromo-estercompound was dissolved in dry CH3CN (70 mL) followed by additiontriphenylphosphine (7.000 g, 26.600 mmol). The reactionmixturewas then refluxed for 36 h. After that solvent evaporated togive gummy residue which was washed with hexanes (20 mL 3)to give compound 19. |
92% | Heating / reflux | Example 15a; General Procedure for the Esterification of Bromoalkanoic Acids (I); Appropriate bromo alkanoic acid (1 equiv) was dissolved in methanol and a catalytic amount of conc.H2SO4 (0.1 mL/g) was added and the reaction mixture was refluxed for overnight. Upon reaction completion, methanol was removed in rotary evaporation and the crude product was washed with aq. NaHCO3, brine solution and extracted with ethyl acetate. The product was used further without column purification.; Example 15d; Synthesis of Methyl 6-Bromohexanoate (11); As mentioned in the general procedure (I), 6-bromohexanoic acid (15 g, 76.9 mmol, 1 equiv) was dissolved in methanol (150 mL), and a catalytic amount of conc.H2SO4 (2 mL) was added and the reaction was carried out. The product was taken to next step without column purification. Yield 14.8 g (92percent). 1H NMR (400 MHz, CDCl3): δ 3.66 (s, 3H), 3.42-3.38 (m, 2H), 2.32 (t, J=7.2 Hz, 2H), 1.90-1.83 (m, 2H), 1.68-1.61 (m, 2H), 1.50-1.44 (m, 2H). 13C NMR (100 MHz, CDCl3); δ 173.9, 51.5, 33.8, 33.4, 32.3, 27.6, 24.0. EI/MS m/z (r.i.) 211 (M+2, 98), 210 (M+1, 8), 209 (M+, 100), 178 (16), 161 (33), 129 (51), 97 (28), 87 (9), 74 (23), 69 (23). |
91% | at 0 - 20℃; | Step 1 Methyl 6-bromohexanoate: At about 0° C., thionyl chloride (11.9 g; 100 mmol; 1.00 equiv) was added dropwise to a stirred solution of 6-bromohexanoic acid (19.5 g; 100 mmol; 1.00 equiv) in methanol (100 mL). The resulting solution was stirred at ambient temperature for about 1 hour and then concentrated in vacuo, to give the title product as a colorless oil (19 g; 91percent yield). 1H NMR (300 MHz, CDCl3) δ 3.68 (s, 3H), 3.41 (t, J=6.6 Hz, 2H), 2.43 (t, J=6.6 Hz, 2H), 1.88 (m, 2H), 1.64 (m, 2H), 1.49 (m, 2H). |
87% | for 16 h; Reflux; Inert atmosphere | General procedure: Typical procedure: After refluxing the mixture of 4a (7.64g, 45.7mmol), methanol (78.4mL), and conc. sulfuric acid (0.77mL) for 16h under a dry argon atmosphere, it was cooled to room temperature. Then, aqueous solution of sodium bicarbonate (78mL) was added to the reaction mixture and the crude product was extracted with ethyl acetate. After washing the combined organic layer with sodium bicarbonate aqueous solution, water, and brine, it was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluted with a mixed solvent of chloroform/methanol (10/1v/v). The fraction with an Rf value of 0.86 was collected and dried under reduced pressure to afford methyl 4-bromobutanoate (5a) |