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CAS No. : | 33036-62-3 | MDL No. : | MFCD00015387 |
Formula : | C4H9BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 153.02 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 6 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 30.37 |
TPSA : | 20.23 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) : | -6.8 cm/s |
Log Po/w (iLOGP) : | 1.7 |
Log Po/w (XLOGP3) : | 0.61 |
Log Po/w (WLOGP) : | 1.15 |
Log Po/w (MLOGP) : | 1.35 |
Log Po/w (SILICOS-IT) : | 1.14 |
Consensus Log Po/w : | 1.19 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.98 |
Solubility : | 16.2 mg/ml ; 0.106 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.61 |
Solubility : | 37.6 mg/ml ; 0.246 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.76 |
Solubility : | 2.66 mg/ml ; 0.0174 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.99 |
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210-P302+P352-P305+P351+P338 | UN#: | 1987 |
Hazard Statements: | H315-H319-H335-H225 | Packing Group: | Ⅱ |
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% | With toluene-4-sulfonic acid In diethyl ether at 0 - 20℃; for 3 h; | To refluxing THF, (0,5 L) 48percent HBr (358 g, 3.9 mol) was added dropwise over a 3.50 hour period. The reaction was refluxed a further 1.5 hours, and then cooled, neutralized with [NAHC03,] partitioned with water, washed with brine, and dried over [MGS04. 83.] 1 g were obtained as a colourless liquid. Then, dyhydropyran (31 mL, 339 mmol) was added via syringe to a cooled solution [(0XB0; C) OF 4-BROMOBUTANOL] (40 g, 261 mmol) in 200 mL of anhydrous ether containing 90 mg [OFP-TOLUENESULFONIC] acid. After 1 hour at [0XB0;C] and 2 h at room temperature, the reaction mixture was washed with saturated sodium bicarbonate solution [(2X80] mL) and brine (1x80 mL). The organic layer was dried over anhydrous [MGS04.] The solution was filtered, and the solvent was removed in vacuo to give 57,4 g (93percent) of product as a colourless oil. The title compound may be obtained as described in Grieco, P. A. , Larsen, S. D. , J. [ORG. CHEM,] 51,3553-3555 (1986). [NMR LH (CDCI3)] : 1.50-1. 65 (m, 4H), 1.65-1. 90 (m, 4H), 1.90-2. 10 (m, 2H), 3.40- 3.60 (m, 4H), 3.75-3. 90 (m, 2H), 4.55-4. 58 (m, 1H). |
92% | With toluene-4-sulfonic acid In dichloromethane at 20℃; | 2-(4-Bromobutoxy)-tetrahydro-2H-pyran (2): 3,4-Dihydro-2H-pyran (8.5 mL, 90.96 mmol) was added dropwise to the dichloromethane (20 mL) solution of 1 (10.7 g, 69.93 mmol) and p-toluenesulfonic acid monohydrate (26.5 mg, 0.1372 mmol). The mixture was stirred at room temperature over night. After removing the solvent, the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent to yield product 2 as a colorless oil (15.3 g, 92 percent). 1H NMR (400 MHz, CDCI3): δ 1.48-1.62 (m, 4H), 1.68-1.85 (m, 4H), 1.94-2.02 (m, 2H), 3.40-3.53 (m, 4H), 3.74-3.88 (m, 2H), 4.57-4.59 (m, 1 H). |
92% | With p-toluenesulfonic acid monohydrate In dichloromethane | 2-(4-Bromobutoxy)-tetrahydro-2H-pyran (52). 3,4-Dihydro-2H-pyran (8.5 mL, 90.96 mmol) was added dropwise to the dichloromethane (20 mL) solution of 51 (10.7 g, 69.93 mmol) and p-toluenesulfonic acid monohydrate (26.5 mg, 0.1372 mmol). The mixture was stirred at room temperature over night. After removing the solvent, the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent to yield product 52 as a colorless oil (15.3 g, 92percent). 1H NMR (400 MHz, CDCl3): δ 1.48-1.62 (m, 4H), 1.68-1.85 (m, 4H), 1.94-2.02 (m, 2H), 3.40-3.53 (m, 4H), 3.74-3.88 (m, 2H), 4.57-4.59 (m, 1H). |
92% | at 20℃; | 2-(4-Bromobutoxy)-tetrahydro-2H-pyran (23): 3,4-Dihydro-2H-pyran (8.5 mL, 90.96 mmol) was added dropwise to the dichloromethane (20 mL) solution of 22 (10.7 g, 69.93 mmol) and p-toluenesulfonic acid monohydrate (26.5 mg, 0.1372 mmol). The mixture was stirred at room temperature over night. After removing the solvent, the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent to yield product 23 as a colorless oil (15.3 g, 92percent). 1H NMR (400 MHz, CDCl3): 1.48-1.62 (m, 4H), 1.68-1.85 (m, 4H), 1.94-2.02 (m, 2H), 3.40-3.53 (m, 4H), 3.74-3.88 (m, 2H), 4.57-4.59 (m, 1H). |
92% | With toluene-4-sulfonic acid In dichloromethane at 20℃; | 3,4-Dihydro-2H-pyran (8.5 mL, 90.96 mmol) was added dropwise to the dichloromethane (20 mL) solution of 19 (10.7 g, 69.93 mmol) and p-toluenesulfonic acid monohydrate (26.5 mg, 0.1372 mmol). The mixture was stirred at room temperature over night. After removing the solvent, the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent to yield product 20 as a colorless oil (15.3 g, 92percent). 1H NMR (400 MHz, CDCl3): 1.48-1.62 (m, 4H), 1.68-1.85 (m, 4H), 1.94-2.02 (m, 2H), 3.40-3.53 (m, 4H), 3.74-3.88 (m, 2H), 4.57-4.59 (m, 1H). |
88% | With toluene-4-sulfonic acid In dichloromethane at 0℃; | 3,4-Dihydro-2H-pyran (8.0 g, 95.36 mmol) was added to a 0°C solution of 4-bromobutan-1-ol (12.0 g, 79.47 mmol) in dichloromethane (150 mL) followed by p-toulenesulphonic acid (20 mg). After 1 h, the reaction was carefully quenched with sat. aq. NaHCO3 solution (5 mL), washed with water (100 mL), brine (70 mL), and concentrated in vacuo. The residue was purified by SiO2 column chromatography using 2percent EtOAc/hexanes as eluent to give 2-(4-bromobutoxy)tetrahydro-2H-pyran (16.57 g, 88percent) as colorless oil. TLC: 10percent EtOAc/hexanes, Rf 0.50; 1H NMR (CDCl3, 300 MHz) δ 4.58 (t, J = 2.5 Hz, 1H), 3.90-3.72 (m, 2H), 3.38-3.50 (m, 4H), 1.92-2.04 (m, 2H), 1.65-1.80 (m, 4H), 1.60-1.50 (m, 4H). Lit. ref:. |
33% | With pyridinium p-toluenesulfonate In dichloromethane | 4-bromo-l-butanol (1), 3g, was treated with 1.5 eq of 3, 4-dihydro-2H-pyran and 0.1 eq of pyridinium j>αroe tuloenesulfonate (PPTS) in 135 mL Of CH2Cl2. After work-up and purification, 1.45 g (33percent) of product 2 was obtained. 1.0 eq of diethylmethylmalonate was deprotonated with 1 eq of NaH and 1.0 eq of bromide 2 was added along with catalytic amount of KI at 5O0C. A complete conversion was observed after 10 hours and a 90percent yield was obtained. Deprotection of tetrahydo pyran (THP) with PPTS in ethanol at 550C went smoothly. After work-up, a quantitative yield of alcohol 4 was obtained and directly used for the mesylation reaction. With the mesylate 5 in hand, a kryptofix- mediated fluorination was performed. Compound 6 was obtained in 68percent yield. |
0.9 g | With toluene-4-sulfonic acid In dichloromethane at 0 - 20℃; for 0.5 h; Inert atmosphere | To a stirred solution of 4-bromobutanol (1 g, 6.53 mmol) in CH2CI2 (15 mL) was added 3,4- dihydro-2H-pyran (824 mg, 9.79 mmol) followed by p-TSA (124 mg, 0.65 mmol) at 0 °C under inert atmosphere. The resulting reaction mixture was stirred for 30 min at RT. After completion of the reaction (by TLC), the reaction mixture was diluted with water and extracted with CH2C12 (2x25 mL). The combined organic extracts were dried over anhydrous Na2S04 and concentrated under reduced pressure to furnish the crude. The crude material was purified by silica gel column chromatography eluting with 5percent EtOAc/hexane as eluent to afford 2-(4-bromobutoxy)tetrahydro-2H-pyran (0.9 g, 3.79 mmol, 58.4percent) as a colorless syrupy mass. *H NMR (500 MHz, CDC13): δ 4.57-4.56 (m, 1H), 3.87-3.74 (m, 2H), 3.51-3.40 (m, 4H), 2.00-1.94 (m, 2H), 1.84-1.68 (m, 4H), 1.61-1.51 (m, 4H). |