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CAS No. : | 155130-15-7 | MDL No. : | |
Formula : | - | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NSODVVYOWINKAG-UHFFFAOYSA-N |
M.W : | - | Pubchem ID : | 15198040 |
Synonyms : |
PEG5-Tos
|
Num. heavy atoms : | 26 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.65 |
Num. rotatable bonds : | 16 |
Num. H-bond acceptors : | 8.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 94.35 |
TPSA : | 108.9 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) : | -8.57 cm/s |
Log Po/w (iLOGP) : | 3.98 |
Log Po/w (XLOGP3) : | 0.17 |
Log Po/w (WLOGP) : | 1.84 |
Log Po/w (MLOGP) : | 0.18 |
Log Po/w (SILICOS-IT) : | 2.29 |
Consensus Log Po/w : | 1.69 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.5 |
Solubility : | 12.6 mg/ml ; 0.032 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.01 |
Solubility : | 3.8 mg/ml ; 0.00967 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.81 |
Solubility : | 0.00602 mg/ml ; 0.0000153 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.66 |
Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
79% | With sodium iodide; silver(I) oxide; In dichloromethane; at 0 - 20℃; for 1h; | To a solution of 3,6,9,12-tetraoxatetradecane-1,14-diol (10 g, 41.96 mmol, CAS4792-15-8), silver oxide (14.6 g, 62.94 mmol) and NaI (7 g, 46.56 mmol) in DCM (250 mL) was added tosyl chloride (8.5 g, 41.96 mmol) at 0 C. The reaction mixture was then allowed to warm to rt and stirred for 1 h. The reaction mixture was then filtered through celite and the filtrate was washed with 10% NaHCO3 solution (125 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was then evaporated under reduced pressure and the crude product was purified using silica gel column chromatography (3% MeOH-DCM) to give 14-hydroxy-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate as a yellow oil (13 g, 79%). LC-MS (ESI+) m/z 394.3 (M+H)+. |
77% | With potassium iodide; silver(I) oxide; In dichloromethane;Cooling; | To a cold and stirred solution of pentaethylene glycol (1 eq) in DCM (amount×10 mL) were added Ag2O (1.5 eq), TsCl (1.1eq) and KI (0.2 eq). After stirring for 30 to 60 min, the precipitated silver salts were removed by filtration through a pad of Celite and washed thoroughly with EtOAc. The combined filtrate was concentrated under vacuum, and the residue was purified by silica gel chromatography to give a colorless oil, yield 77%. LC/MS (ESI) m/z: 393.2 [M+1] +; 1H-NMR (400MHz, CDCl3) d 2.45 (s, 3H), 3.59-3.73 (m, 18H), 4.16 (t, J = 4.8 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 7.80 (d, J = 8.0 Hz, 2H). |
75% | With potassium iodide; silver(I) oxide; In dichloromethane; at 0℃; for 0.333333h; | 14-Hydroxy-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate (26) To a chilled (0 C.) solution of pentaethylene glycol (2.13 g, 8.92 mmol) in DCM (89 mL) were added TsCl (1.87 g, 9.81 mmol), Ag2O (3.10 g, 0.134 mmol), and KI (0.296 g, 1.78 mmol). After stirring for 20 min the reaction mixture was filtered through a 4 cm pad of celite and flushed with EtOAc. The resulted filtrate was concentrated under reduced pressure to give a yellow oil. The crude product was purified via silica flash chromatography using 3:2 DCM/acetone as an eluent, providing 26 (2.63 g, 75%): 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=8.2 Hz, 2H), 7.34 (d, J=8.2 Hz, 2H), 4.20-4.11 (m, 2H), 3.76-3.54 (m, 18H), 2.44 (s, 3H). |
74% | With triethylamine; In dichloromethane; at 0 - 20℃; for 18h;Inert atmosphere; | Protocole 2 A solution of pentaethylene glycol (0.04 mmol ; 25.00 g) in dry CH2Cl2 (15 mL), under argon, was cooled to 0C with an ice bath and triethylamine (0.015 mmol ; 2.10 mL). Subsequently p-toluenesulfonyl chloride (0.0104 mmol ; 1.98 g) was added in the portions to the cooled reaction mixture. After complete addition, the solution was allowed to warm to room temperature and was stirred for 18 h. The mixture was washed with water (3 x 100 mL), the aqueous layers were re-extracted with CH2Cl2 and the combined organic layers washed with 5% citric acid (3 x 25 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The product was purified by flash column chromatography on silica gel (99% CH2Cl2/MeOH) to give the desired compound 3e as a colorless oil in 74% yield (3.01 g). |
69% | To a solution of 2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethanol (15 g, 62.95 mmol, 13.27 mL, 2 eq) in tetrahydrofuran (150 mL) was added sodium hydride (1.26 g, 31.48 mmol, 60% purity, 1 eq) at 0 C. The mixture was stirred at 0 C for 0.5 hour. Then p- toluenesulfonyl chloride (6.00 g, 31.48 mmol, 1 eq) was added, the mixture was stirred at 25 C for 2 hours. The mixture was poured into saturated ammonium chloride aqueous solution (100 mL), the water layer was extracted with ethyl acetate (80 mL x 2). Then the organic phase was dried over anhydrous sodium sulfate, filtered and the filtrate was condensed to get the residue. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 3/1 to dichloromathane/methanol = 10/1) to get 2-[2-[2-[2-(2- hydroxyethoxy)ethoxy] ethoxy] ethoxy] ethyl 4-methylbenzenesulfonate (8.62 g, 21.96 mmol, 69% yield) as a light yellow oil. | |
66% | With triethylamine; In dichloromethane; at 20℃; for 15h; | The compound tetrapentaethylene glycol (6.0 g, 25.2 mmol) was dissolved in 20 mL of dichloromethane, and triethylamine (4.9 g, 48, 4 mmol) was added dropwise while TsCl was placed in dichloromethane. The funnel was slowly added dropwise to the solution and stirred at room temperature for 15 h.The reaction was monitored by thin layer chromatography (EA) and the TsCl portion of the compound remained.The solution was adjusted to pH = 7 with 4M HCl, 10 mL of water was added, and extracted three times with 30 mL of dichloromethane.Column chromatography (EA) gave a product of 6.52 g, yield 66%. |
61.22% | With silver(I) oxide; In dichloromethane; at 0 - 20℃; for 2h; | Into a 500-mL round-bottom flask, was placed 3,6,9,12-tetraoxatetradecane-1,14-diol (9.53 g, 39.995 mmol, 1 equiv) in dichloromethane (200 mL), to which was added Ag2O (13.90 g, 59.982 mmol, 1.50 equiv) and TsCl (7.78 g, 40.808 mmol, 1.02 equiv) at 0 in a water/ice bath. Then KI (1.33 g, 8.012 mmol, 0.20 equiv) was added. The resulting mixture was stirred for 2 hr at room temperature. The solids were filtered out and the filtrate was concentrated under vacuum. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (12/1). This resulted in 9.61 g (61.22%) of 14-[(4- methylbenzenesulfonyl)oxy]-3,6,9,12-tetraoxatetradecan-1-ol as a light yellow oil. MS (ES+): m/z 392.95[MH+] |
51% | With potassium iodide; In dichloromethane; at 20℃; | Into a 250-mL round-bottom flask, was placed a solution of 3,6,9,12-tetraoxatetradecan-1,14-diol (5.0 g, 20.98 mmol, 1.00 equiv) in dichloromethane (100 mL), Ag2O (7.3 g, 31.50 mmol, 1.50 equiv), 4-methylbenzene-1-sulfonyl chloride (4.0 g, 20.99 mmol, 1.00 equiv ), KI (695.0 mg, 4.19 mmol, 0.30 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of water (80 mL). The solids were filtered out. The resulting solution was extracted with dichloromethane (60 ml x 3) and the organic layers combined. The resulting mixture was washed with brine (60 ml x 1), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1/1). This resulted in 4.2 g (51 %) of 14-[[4-methylbenzenesulfonyl]oxy]-3,6,9,12-tetraoxatetradecan-1-ol as yellow oil. |
46% | With triethylamine; In dichloromethane; at 0 - 20℃; for 16h; | The title compound (6.1 g, 46%) was furnished as a colorless oil. It was prepared from 3,6,9,12-tetraoxatetradecane-1,14-diol (8.0 g, 33.57 mmol) following the procedure outlined for Example 2, Step 1. 1H NMR (400 MHz, CDCl3): δ 7.80 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 4.16 (t, J = 4.8 Hz,, 2H), 3.72 - 3.58 (m, 18H), 2.45 (s, 3H). |
43% | With N-Trimethylamine hydrochloride; triethylamine; In dichloromethane; for 18h; | A solution of pentaethylene glycol (35g, 147mmol), TEA (41mL, 294mmol) and trimethylamine-HCl (1.4g, 14.7mmol) in CH2C12 (600mL) was treated with tosyl chloride (29.4g, 154mmol). After stirring (18h) the reaction mixture was washed with H20-brine (1 :1), dried (MgS04), filtered, concentrated and subjected to chromatography to yield 82 (24.6g, 43%) as a pale yellow oil. Rf 0.8 (10% CH30H-CH2C12). |
43% | With N-Trimethylamine hydrochloride; triethylamine; In dichloromethane; for 18h; | A solution of pentaethylene glycol (35g, 147mmol), TEA (41mL, 294mm ol) and trimethylamine-HCl (1.4g, 14.7mmol) in CH2CI2 (600mL) was treated with tosyl chloride (29.4g, 154mmol). After stirring (18h) the reaction mixture was washed with EbO-brine (1 : 1), dried (MgS04), filtered, concentrated and subjected to chromatography to yield 82 (24.6g, 43%) as a pale yellow oil. Rf 0.8 (10% CH3OH-CH2CI2). |
43% | With N-Trimethylamine hydrochloride; triethylamine; In dichloromethane; for 18h; | A solution of pentaethylene glycol (35g, 147mmol), TEA (41mL, 294mmol) and trimethylamine-HCl (1.4g, 14.7mmol) in CH2CI2 (600mL) was treated with tosyl chloride(29.4g, 154mmol). After stirring (18h) the reaction mixture was washed with EhO-brine (1 : 1), dried (MgS04), filtered, concentrated and subjected to chromatography to yield 82 (24.6g, 43%) as a pale yellow oil. Rf 0.8 (10% CH3OH-CH2CI2). |
43% | With N-Trimethylamine hydrochloride; triethylamine; In dichloromethane; for 18h; | A solution of pentaethylene glycol (35g, 147mmol), TEA (41mL, 294mmol) and trimethylamine-HCl (1.4g, 14.7mmol) in CH2Cl2 (600mL) was treated with tosyl chloride (29.4g, 154mmol). After stirring (18h) the reaction mixture was washed with H2O-brine (1:1), dried (MgSO4), filtered, concentrated and subjected to chromatography to yield 82 (24.6g, 43%) as a pale yellow oil. Rf 0.8 (10% CH3OH-CH2Cl2). |
42% | With triethylamine; | To a stirred solution of 3,6,9,12-tetraoxatetradecane-1,14-diol (70 g, 293.8 mmol) in DCM (500 mL) was added TEA (29.7 g, 293.8 mmol) followed by the addition of a solution of 4- methylbenzene-1-sulfonyl chloride (56.0 g, 293.8 mmol) in DCM (500 mL) over 30 min at room temperature under nitrogen atmosphere. The resulting solution was stirred for an additional 16 h at room temperature. Upon completion, the resulting solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluted with EtOAc to afford 14-[(4-methylbenzenesulfonyl)oxy]-3,6,9,12-tetraoxatetradecan-1-ol (48 g, 42%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) d 7.81 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 4.17 (t, J = 4.9 Hz, 2H), 3.80-3.56 (m, 18H), 2.50 (d, J = 4.4 Hz, 1H), 2.46 (s, 3H) LC/MS (ESI, m/z): [(M + 1)]+ = 393.00 |
38% | With potassium iodide; silver(I) oxide; In dichloromethane; at 0 - 20℃; for 16h; | To a solution of 3,6,9,12-tetraoxatetradecan-1,14-diol (0.50 g, 2.1 mmol), potassium iodide (69 mg, 0.42 mmol), and silver oxide (48 mg, 0.21 mmol) in methylene chloride (50 ml) was added p-toluenesulfonyl chloride (0.36 g, 1.9 mmol) at 0 C., and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was purified by preparative TLC (methylene chloride:methanol=10:1) to give Compound (p-2) (0.31 g, 38% yield). (1171) 1H-NMR (CDCl3, 400 MHz) δ: 7.80 (d, J=8.4 Hz, 2H), 7.34 (d, J=8.4 Hz, 2H), 4.17-4.15 (m, 2H), 3.71-3.60 (m, 19H), 2.45 (s, 3H). |
With triethylamine; In tetrahydrofuran; | FIGURE 36 shows the synthetic scheme used to obtain IBA-GN3. Pentaethylene glycol was treated with tosyl chloride in the presence of base to give the mono-tosylated alcohol, which was then treated with sodium azide at elevated temperature to give the azidoalcohol. This compound was then oxidized using Jones reagent, then reduced with Palladium on carbon under hydrogen atmosphere to give a carboxylic acid-amine. Separately, indole butyric acid was treated with N-hydroxysuccinimide, EDC, and DIPEA to give the NHS-ester indole, which was then reacted with the above carboxylic acid-amine. The product was again reacted with N-hydroxysuccinimide, EDC, and DIPEA to give a NHS ester. This NHS ester was reacted with NH2-GN3, which was prepared as described previously. The subsequent amide was deprotected with NaOMe in MeOH to give compound IBA-GN3. | |
With sodium hydroxide; In tetrahydrofuran; water monomer; at 0 - 20℃; for 2h; | General procedure: Tetraethylene glycol (10.0g, 51.5mmol) was dissolved in tetrahydrofuran (30mL) at 0C. An aqueous solution of sodium hydroxide (0.3g, 7.7mmol) and TsCl (1.0g, 5.2mmol) were added to the reaction solution, stirred at 0C for 5min, and then stirred at room temperature for 2h. After the completion of the reaction, the reaction solution was filtered, and the filter cake was rinsed with dichloromethane. The filtrate was concentrated and washed twice with 10% NaHCO3 solution. The organic phase was concentrated and dried to obtain 1.7g of a colorless oil V-1 with a yield of 93%. | |
With sodium hydroxide; In tetrahydrofuran; water monomer; at 0 - 20℃; for 2h; | General procedure: Tetraethylene glycol (10.0g, 51.5mmol) was dissolved in tetrahydrofuran (30mL) at 0C. An aqueous solution of sodium hydroxide (0.3g, 7.7mmol) and TsCl (1.0g, 5.2mmol) were added to the reaction solution, stirred at 0C for 5min, and then stirred at room temperature for 2h. After the completion of the reaction, the reaction solution was filtered, and the filter cake was rinsed with dichloromethane. The filtrate was concentrated and washed twice with 10% NaHCO3 solution. The organic phase was concentrated and dried to obtain 1.7g of a colorless oil V-1 with a yield of 93%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With pyridinium p-toluenesulfonate; In dichloromethane; for 3h;Reflux; | 14-(Tetrahydro-2H-pyran-2-yloxy)-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate (27) To a solution of 26 (2.613 g, 6.66 mmol) in DCM (100 mL) were added pyridinium p-toluenesulfonate (0.335 g, 1.33 mmol) and 2,3-dihydro-2H-pyran (0.91 mL, 9.99 mmol). The resulting mixture was refluxed for 3 h. After cooling the solution was concentrated under vacuum, poured into ice-water, and extracted with DCM. The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and concentrated to give a yellow oil. The crude product was purified via silica flash chromatography using 4:1 EtOAc/Hex as an eluent, furnishing 27 (2.91 g, 92%): 1H NMR (300 MHz, CDCl3) δ 7.79 (d, J=8.2 Hz, 2H), 7.33 (d, J=8.2 Hz, 2H), 4.67-4.57 (m, 1H), 4.19-4.11 (m, 2H), 3.93-3.78 (m, 2H), 3.71-3.54 (m, 18H), 2.44 (s, 3H), 1.92-1.41 (m, 6H). |
79% | With pyridinium p-toluenesulfonate; In dichloromethane; at 20℃; for 16h; | Into a 250-mL round-bottom flask, was placed 14-[(4-methylbenzenesulfonyl)oxy]- 3,6,9,12-tetraoxatetradecan-1-ol (9.22 g, 23.493 mmol, 1 equiv) in dichloromethane (150 mL), to which was added DHP (2.17 g, 25.798 mmol, 1.10 equiv) and PPTS (1.18 g, 4.696 mmol, 0.20 equiv) in sequence. The resulting mixture was stirred for 16 hr at room temperature. The mixture was quenched by 100 mL water and extracted with ethyl acetate (50 mL x 3). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (3/2). This resulted in 8.84 g (79%) of the title compound as a light yellow oil. MS (ES+): m/z 499.10 [MNa+] |
12.5 g | With pyridinium p-toluenesulfonate; In dichloromethane; at 0 - 25℃; for 16h; | To a solution of 2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 4- methylbenzenesulfonate (13 g, 33.12 mmol, 1 eq) in dichloromethane (100 mL) was added pyridine 4-methylbenzenesulfonate (416 mg, 1.66 mmol, 0.05 eq) and 3,4-dihydro-2H-pyran (3.34 g, 39.75 mmol, 3.63 mL, 1.2 eq) at 0C. Then the mixture was stirred at 25 C for 16 hours. The mixture was filtrated to get the filtrate. The filtrate was quenched by water (300 mL) and then diluted with dichloromethane (500 mL) and extracted with dichloromethane (500 mL x 2). The combined organic layers were washed with brine (300 mL), dried over, filtered and concentrated under reduced pressure to give a residue. The residue was purified by chromatography on silica gel (petroleum ether /ethyl acetate=3:l) to afford 2-[2-[2-[2-(2- tetrahydropyran-2-yloxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate (12.5 g, 26.23 mmol) as yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With Caswell No. 744A; In N,N-dimethyl-formamide; at 80℃; for 12h; | To a mixture of <strong>[155130-15-7]2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate</strong> (4.50 g, 11.5 mmol) in DMF (30 mL) was added sodium azide (1.86 g, 28.6 mmol). Then the reaction mixture was stirred at 80 C. for 12 h. On completion, the reaction mixture was diluted with water (30 mL) and extracted with a mixture of dichloromethane and methanol (10:1, 3×30 mL). The organic layer was concentrated in vacuo to give the title compound (3.00 g, 99% yield) as a yellowish oil. LC-MS (ESI+) m/z 264.1 (M+H)+. |
94% | With Caswell No. 744A; In ethanol; water monomer; at 80℃; for 16h; | A solution of <strong>[155130-15-7]14-[(4-methylbenzenesulfonyl)oxy]-3,6,9,12-tetraoxatetradecan-1-ol</strong> (44 g, 112.1 mmol) and NaN3 (29.2 g, 448.5 mmol) in EtOH (300 mL) and H2O (300 mL) was stirred for 16 h at 80 oC under nitrogen atmosphere. Upon completion, the resulting solution was concentrated under reduced pressure to remove EtOH. The residue was diluted with water (200 mL) and extracted with EtOAc (4 x 400 mL). The combined organic layers was washed with brine (500 mL) and dried over anhydrous Na2SO4. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluted with 5% methanol in dichloromethane to afford 14-azido-3,6,9,12-tetraoxatetradecan-1-ol (27.7 g, 94%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) d 3.71 (t, J = 4.5 Hz, 2H), 3.66 (s, 14H), 3.60 (t, J = 4.5 Hz, 2H), 3.38 (t, J = 5.1 Hz, 2H), 2.65 (br s, 1H). LC/MS (ESI, m/z): [(M + 1)]+ = 264.00 |
With Caswell No. 744A; In N,N-dimethyl-formamide;Heating; | FIGURE 36 shows the synthetic scheme used to obtain IBA-GN3. Pentaethylene glycol was treated with tosyl chloride in the presence of base to give the mono-tosylated alcohol, which was then treated with sodium azide at elevated temperature to give the azidoalcohol. This compound was then oxidized using Jones reagent, then reduced with Palladium on carbon under hydrogen atmosphere to give a carboxylic acid-amine. Separately, indole butyric acid was treated with N-hydroxysuccinimide, EDC, and DIPEA to give the NHS-ester indole, which was then reacted with the above carboxylic acid-amine. The product was again reacted with N-hydroxysuccinimide, EDC, and DIPEA to give a NHS ester. This NHS ester was reacted with NH2-GN3, which was prepared as described previously. The subsequent amide was deprotected with NaOMe in MeOH to give compound IBA-GN3. |
With Caswell No. 744A; In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: V-1 (1.7g, 4.8mmol) was dissolved in DMF solution, NaN3 (0.5g, 7.2mmol) was added, and the reaction was heated and stirred at 100C. After 12h, H2O was added to the reaction solution to quench the reaction, and then DCM was added and extracted three times. The organic phases were combined and spin-dried to obtain 1.1g of light yellow oily substance V-5, which was directly subjected to the next reaction without purification. | |
With Caswell No. 744A; In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: V-1 (1.7g, 4.8mmol) was dissolved in DMF solution, NaN3 (0.5g, 7.2mmol) was added, and the reaction was heated and stirred at 100C. After 12h, H2O was added to the reaction solution to quench the reaction, and then DCM was added and extracted three times. The organic phases were combined and spin-dried to obtain 1.1g of light yellow oily substance V-5, which was directly subjected to the next reaction without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 16h; | Into a 250-mL round-bottom flask, was placed a solution of 14-[[4-methylbenzenesulfonyl]oxy]-3,6,9,12-tetraoxatetradecan-1-ol (2.0 g, 5.10 mmol, 1.00 equiv) in N,N-dimethylformamide (150 mL), potassium carbonate (2.2 g, 15.92 mmol, 3.00 equiv), 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1.5 g, 6.82 mmol, 1.50 equiv). The resulting solution was stirred for 16 h at 60C in an oil bath. The reaction was then quenched by the addition of water (100 mL) and extracted with ethyl acetate (50 mL x 3). The combined organic layers were washed with brine (80 mL x 2), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1/1). This resulted in 1.2 g (53%) of 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,4,7,10,13-pentaoxapentadecan-15-ol as yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tetrabutylammomium bromide; potassium bromide; In acetone; at 80℃; for 10h; | A solution of Compound (p-2) (0.13 g, 0.32 mmol), potassium bromide (0.11 g, 0.95 mmol), and tetrabutylammonium bromide (0.10 g, 0.32 mmol) in acetone (10 ml) was stirred at 80 C. for 10 hours. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1) to give Compound (p-3) (83 mg, 87% yield). (1174) 1H-NMR (CDCl3, 400 MHz) δ: 3.83-3.79 (m, 2H), 3.74-3.70 (m, 2H), 3.70-3.62 (m, 8H), 3.62-3.61 (m, 2H), 3.49-3.46 (m, 2H), 2.96 (br, 1H), 1.75 (s, 4H). |
Tags: 155130-15-7 synthesis path| 155130-15-7 SDS| 155130-15-7 COA| 155130-15-7 purity| 155130-15-7 application| 155130-15-7 NMR| 155130-15-7 COA| 155130-15-7 structure
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P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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