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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents. 1-Octanol is a highly attractive biofuel with diesel-like properties.
Synonyms: Octanol
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Cure, Hannah L ; Shell, Thomas A ;
Abstract: Substituting hydrogen atoms with fluorine alters physicochemical properties often resulting in improved drug action relative to the parent molecule. The high electronegativity of fluorine changes the electron density distribution of the molecule; however, the substitution does not significantly change the size of the molecule because hydrogen and fluorine have similar atomic radii. A trifluoroacetamido derivative (TFA-phenacetin) of phenacetin, an analgesic antipyretic drug, was synthesized to compare its lipophilicity to the parent molecule by determining octanol–water partition coefficients. TFA-phenacetin is over seven times more lipophilic than phenacetin, which suggests that TFA-phenacetin would have better bioavailability relative to phenacetin. The kinetics of cytochromes P-450 (CYP) catalyzed oxidation of phenacetin and TFA-phenacetin were compared using Sprague Dawley (SD) rat liver microsomes. Phenacetin and TFA-phenacetin have the same apparent binding affinity for the SD rat liver microsome CYP proteome and undergo CYP catalyzed oxidation at the same rate in the presence of SD rat liver microsomes.
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Keywords: Phenacetin ; Fluorine derivative ; Lipophilicity
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CAS No. : | 111-87-5 |
Formula : | C8H18O |
M.W : | 130.23 |
SMILES Code : | CCCCCCCCO |
Synonyms : |
Octanol
|
MDL No. : | MFCD00002988 |
InChI Key : | KBPLFHHGFOOTCA-UHFFFAOYSA-N |
Pubchem ID : | 957 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H227-H319-H402-H412 |
Precautionary Statements: | P210-P264-P273-P280-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501 |
* 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 dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | General procedure: To a solution of Tscl (2.86 g, 15 mmol) and DMAP (166 mg,1 mmol) in DCM (30 mL), triethylamine (2.1 mL, 15 mmol) and hexyl alcohol (1.58 mL, 10 mmol) in DCM (20 mL) was addeddropwise at 0 C, and the mixture was allowed warm to rt andstirred for 1 h, the solvent was evaporated in vacuo, the residuewasdissolved by ethyl acetate (EA) and washed with satd aq NaHCO3,the organic layer was dried with Na2SO4, filtered, concentrated, andpurified by column chromatography to afford 11 as yellow solid(2.7 g, 95%). |
With pyridine; In dichloromethane; | General procedure: Alcohol (8.74 g of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanol or 3.13 g of octanol, 24 mmol) and tertiary amine (30 mmol, triethylamine (4.2 ml) in the case of fluorinated alcohol and pyridine (2.4 ml) in the case of octanol) were dissolved in 50 ml of dichloromethane and p-toluenesulfonyl chloride (4.77 g, 25 mmol) was added in small portions. The reaction mixture was stirred overnight. The dichloromethane solution was then washed with water, dried over anhydrous MgSO4 and evaporated in vacuo. The crude product was crystallized from methanol in the case of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl tosylate. Crude octyl tosylate was used in the next step without further purification. | |
With pyridine; at 10 - 20℃; for 3h; | General procedure: 4-Methylbenzenesulphonyl chloride (55 mmol) was added slowly to a mixture of a primary alcohol (50 mmol) and 20 ml of pyridine at 10 C. The reaction mixture was stirred for 3 h at 20 C. After that 120 ml of 25 % hydrochloric acid was slowly added. The reaction mixture was then extracted with chloroform, organic layer dried with Na2SO4 and evaporated to yield alkyl 4-methylbenzenesulphonate as colourless oily liquid or white solid, which was used without further purification. Ethyl 4-methylbenzenesulphonate was purchased from Fluka. |
With trimethylamine hydrochloride; triethylamine; In acetonitrile; at 0℃; for 1h; | General procedure: The reaction of 1-octanol, 2-octanol, phenol and piperidine was performed according to the method described by Yoshida et al. 20 The activating agent, TsCl or CymCl, was present in 1.50 molar equivalents and dissolved in 1 mL of the chosen solvent. The solution was added drop-wise to a reagent mixture composed of 1.00 mmol of the chosen nucleophile, 1 molar equivalent of Me3N.HCl in 2.5 molar equivalents of Et3N, all dissolved in 1 mL of the chosen solvent in ice bath under magnetic stirring. The solvent was toluene, p-cymene or acetonitrile. After one hour, the reaction mixture was quenched with water, extracted with ethyl acetate, then washed with brine, dried with MgSO4 and concentrated in vacuo to give the crude arylsulphonyl derivative of the substrate that was analyzed by GC-FID, GC-MS, NMR spectroscopy and IR spectroscopy as appropriate. The conversion was calculated using GC-FID of the crude mixture against a calibration curve. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid; In toluene; at 80 - 125℃; | In step 1 of Figure 1, in a 1 liter round bottom flask, 136 g of 1-octanol was mixed with 350 g of toluene, the flask was placed in a heating mantle and maintained on a magnetic stirrer,The mixture was stirred vigorously at 80 DEG C to form a mixed solution.As step 120 of Figure 1,86 g of 2-cyanoacetic acid and 0.5 g of p-toluenesulfonic acid were gradually added to the flask, and a water condenser was connected to the flask through a trap and a calcium chloride guide tube.The temperature was 125 CAnd the esterification reaction was carried out.As step 130 of Figure 1, the water formed during the esterification reaction was azeotrope-formed and removed while azeotropic distillation was continued until the total amount of water collected was 17 mL. The distillation was then stopped and the flask was cooled to room temperature. The contents of the flask were filtered with a Buchner funnel, and the filtrate was extracted three times with a 10% sodium hydrogencarbonate solution and water using a 1 liter separatory funnel, respectively. The obtained organic layer was dried over anhydrous magnesium sulfate for 12 hours.Then toluene was added to 85In And then removed by rotary evaporation.Results 1-Octyl-2-cyanoacetate was analyzed by FT-IR spectrophotometer and the results are shown in FIG. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Description 14-(octyloxy)-3-(trifluoromethyl)benzoic acid (D1)A 1.5M solution of NaHM with THF (4.5 vol) and n- octanol (1.52 vol; 2eq) is charged and heated to 55-600C. A solution of 4-fluoro-3- (trifluoromethyl)benzoic acid (1 wt, 1eq) in THF (2 vol) is charged, washing through with further THF (1 vol). The reaction mixture is stirred at 57+/-3 0C until deemed <n="12"/>complete by HPLC (ca. 24h, <4% area <strong>[67515-55-3]4-fluoro-3-(trifluoromethyl)benzoic acid</strong> remaining). The reaction is then cooled to 20-250C and solvent swapped into water (10vol) by vacuum distillation (remove ca. 15vol distillate) to afford a tan slurry which is extracted into TBME (10vol). Water (10vol) is charged to the organic layer, and the product is extracted into the aqueous layer. The aqueous layer is washed with TBME (4 x 5vol), then acidified with 5N HCI (3 vol) and extracted into TBME (2x5vol). The combined organic extracts are washed with water (3x5vol) and 15% brine solution (4vol), then dried over magnesium sulphate (0.2 wt) and filtered, washing through with further TBME (2 vol). The volatiles are removed under vacuum to afford a tan solid of D1 (1.02 kg; 96%th.; 146% w/w). | |
With potassium tert-butylate; In tetrahydrofuran; at 75℃; for 3 - 4h;Product distribution / selectivity; | 1-octanol (315 muL, 2.0 mmol), THF (5 mL), potassium -butoxide (5 mL, IM solution in THF), 4-Fluoro-3-trifluoromethylbenzoic acid (417 mg, 2.0 mmol) were mixed and heated at 75 0C for 3-4hrs. The reaction mixture was then diluted with ethyl acetate and washed with water. The water layer was acidified and extracted with ethyl acetate. The <n="151"/>organic layer was washed with brine and dried OVCrNa2SO4 and concentrated to afford the title compound (632 mg, HPLC purity > 95%), which was used for next reaction without further purification. HPLC retention time on a C8(2) column (30 x 3.00 mm, 3 mu) was 3.28 min with gradient 50-98% acetonitrile-H2O (0.1% trifluoroacetic acid (TFA)) in 3.5 min as mobile phase. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With triphenylphosphine; In dichloromethane; | REFERENCE EXAMPLE 12 Synthesis of ethyl 6-methoxy-4-octyloxyquinoline-3-carboxylate The quinolinol derivative (2.47 g, 10 mmol) synthesised in Reference Example 2 was dissolved in methylene chloride (70 ml). Thereto were added, at room temperature, 1-octanol (3.26 g, 25 mmol), triphenylphosphine (3.93 g, 15 mmol) and diethyl azodicarboxylate (2.61 g, 15 mmol). The mixture was stirred at room temperature for 4 hours and then diluted with chloroform (200 ml). The resulting material was washed with water. The organic layer was dried over anhydrous magnesium sulfate and then subjected to vacuum concentration. The residue was purified by silica gel column chromatography (equivalent product of Merck C-300: 100 g, ethyl acetate:hexane=1:5) to obtain an intended title compound (2.82 g, 79%) as a light yellow transparent syrup. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In methanol; ethanol; hexane; dichloromethane; water; acetone; | Reference Example 11 Production of (+-)-1-(cyclohexyloxycarbonyloxy)ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimidazole-7-carboxylate [Compound B] To the solution of (+-)-<strong>[170791-09-0]1-(cyclohexyloxycarbonyloxy)ethyl 2-ethoxy-1-[[2'-(1-triphenylmethyl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate</strong> [Compound B(T)] obtained in Reference Example 10, were added methylene chloride (28 L) and methanol (161 L), and the solution was cooled to -5+-5 C. while stirring. To the solution was added dropwise methanolic hydrogen chloride (hydrogen chloride 4.4 kg dissolved in methanol 47 L) at 0 C. or less for 15+-5 minutes. The solution was stirred at -5+-5 C. for about 2 hours. To the reaction solution were added methylene chloride (209 kg) and pure water (303 L), and the pH of the solution was adjusted to pH about 6.3 at 5 C. or less with 7.0 w/v % sodium bicarbonate solution. The methylene chloride layer was separated, and the aqueous layer was extracted with methylene chloride (209 kg). The methylene chloride layers were combined and washed with water (157 L) and concentrated to 173 kg or less. To the residue was added acetone (124 kg), and the solution was concentrated to 154 kg. To the residue were added ethanol (24 L) and seed crystals, and the solution was stirred at room temperature for 3-5 hours to precipitate crystals. To the resulting mixture was added ethanol (12 L), and the solution was stirred at room temperature for about 30 minutes. To the mixture was added dropwise hexane (363 kg) for about 30 minutes, and the solution was stirred at room temperature for about 1 hour and then at 5+-5 C. for about 2 hours to precipitate crystals and age. The separated crystals were separated, washed with a mixture of ethanol-hexane (1:9) (247 L) and dried to give crude crystals of (+-)-1-(cyclohexyloxycarbonyloxy)ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate [Compound B] (49.5 kg; 88.0%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium tert-butylate; In tetrahydrofuran; at 115℃; for 0.0166667h;Microwave irradiation; | <strong>[67515-59-7]4-fluoro-3-(trifluoromethyl)benzonitrile</strong> (1 equiv) and the alcohol (1 equiv) were added to a microwave vial and cooled in an ice bath, then 0.5M potassium tert- butoxide in tetrahydrofuran (1.1 equiv) was carefully added and allowed to warm to room temperature. The contents were then heated to 115 C for 1 minute in the microwave. After cooling, celite was added and the solvent was removed under reduced pressure. The resulting powder was subjected to flash chromatography on silica gel. |
96% | With potassium tert-butylate; In tetrahydrofuran; at 115℃; for 0.0166667h;Cooling with ice; Microwave irradiation; | General procedure: <strong>[67515-59-7]4-fluoro-3-(trifluoromethyl)benzonitrile</strong> (1 equiv) and the alcohol (1 equiv) were added to a microwave vial and cooled in an ice bath, then 0.5M potassium tert-butoxide in tetrahydrofuran (1.1 equiv) was carefully added and allowed to warm to room temperature. The contents were then heated to 1 15 C for 1 minute in the microwave. After cooling, celite was added and the solvent was removed under reduced pressure. The resulting powder was subjected to flash chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | Preparation of 4-{5-[Bis-(chloroethyl)-amino]-l-methyl-lH-benzimidazol-2-yl}butyric aid octyl ester (<strong>[3543-75-7]bendamustine</strong> Cg ester): A 250 mL three neck round bottom flask was equipped with an overhead stirrer, thermocouple, temperature controller and nitrogen sweep then charged with 10.0 g (25.34 mmol) of <strong>[3543-75-7]<strong>[3543-75-7]bendamustine</strong> hydrochloride</strong>, 3.33 g (4.03 mL, 25.6 mmol, 1.01 eq) of 1-octanol, 5.3 g (25.6 mmol, 1.01 eq) of dicyclohexylcarbodiimide (DCC), 100 mL of MDC and 0.3 1 g (2.54 mmol, 0.1 eq) of DMAP. The reaction was stirred at room temperature overnight at which time an in process analysis indicated the reaction was complete. Solids were removed by vacuum filtration and washed with 25 mL of MDC. The filtrate was washed with saturated aqueous sodium bicarbonate solution (2 X 100 mL), DI water (1 X 100 mL) and brine (1 X 100 mL) before drying over sodium sulfate, filtering and concentrating to dryness in vacuo to a brown oil. The oil was triturated with 25 mL of MDC and the solid impurities were removed by vacuum filtration and washed with 5 mL of MDC. The filtrate was concentrated to dryness in vacuo to yield 9.7 g (20.5 mmol, 81%) of the product as a clear light brown oil with an HPLC purity of 91.9A%. NMR (400 MHz, CDC13) delta 7.17 (d, J= 8.76 Hz, 1H), 7.08 (d, J = 2.28 Hz, 1H), 6.77 (dd, J = 2.4, 8.76 Hz, 1H), 4.05 (t, J= 6.8 Hz, 2 H), 3.72 (m, 4H), 3.69 (s, 3H), 3.63 (m, 4H), 2.91 (t, J= 7.44 Hz, 2H), 2.49 (t, J = 7.12 Hz, 2H), 2.18 (m, 2H), 1.60 (m, 2H), 1.32 (m, 10H), 0.89 (t, J= 6.72 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 16h; | [00222] To a mixture of <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (700 mg, 5.4 mmol, 1.0 eq), octan-1-ol (1.05 g, 8.1 mmol, 1.5 eq), PPh3 (2.8 g, 10.8 mmol, 2.0 eq) and triethylamine (1.63 g, 16.2 mol, 3.0 eq) in THF (14 mL) was added dropwise DIAD (2.18 g, 10.8 mmol, 2.0 eq) at 0 °C. The mixture was allowed to warm up to rt and stirred for 16 h. The solvent was then removed under reduced pressure and the residue was purified by column chromatography on silica gel (PE/EA=10/1) to give the title compound as a yellow oil (847 mg, 65percent yield). LCMS mlz 243.1 [M+H] 1H NMR (CDC13, 400 MHz) 5: 8.28 (s, 2H), 4.05 (t, J= 6.8 Hz, 2H), 1.85-1.78 (m, 2H), 1.42-1.26 (m, 1OH), 0.90-0.86 (m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.8% | With CBV600; at 110℃; for 0.0833333h;Microwave irradiation; Inert atmosphere; | 10143] A mixture of 3.0 mmol of <strong>[3027-21-2]methylphenyldi(methoxy)silane</strong> (Ia), 3.3 mmol of octanol (lie) and 10mg of CBV 600 (by Zeolyst International) was charged into a reaction tube, with stirring for 5 minutes at 1100 C., using a microwave irradiation device (Discover by CEM Corporation), understream of nitrogen gas at a flow rate of 50 mE/minute, in an open system. The resulting product was analyzed using a gas chromatograph and a gas chromatographlmass spectrometet The analysis results revealed that octoxysilane (Ille) (mixture of IIIe-1: methylphenyl(methoxy)(octoxy)silane and IIIe-2:methylphenyldi(octoxy)silane, IIIe-1: IIIe-2=97:3) was generated with a yield of 95.8percent. |
With CBV600; at 80℃; for 0.0833333h;Microwave irradiation; | General procedure: di(methoxy)(methyl)(phenyl) silane (IIIa) 1.6mmol, 2-methoxyethanol (IVa) 3.2mmol, CBV780 (Zeolyst Co., Ltd.) 5 mg of the mixture in the reaction tube, 10 minutes at room temperature (25 °C ). An analysis result of a product gas chromatograph (GC), gas chromatograph/mass spectrometer (GC-MS), in nuclear magnetic resonance spectrum analyzer (NMR)and, as a product, di(2-methoxyethoxy)silane(phenyl)(methyl) (Va-2) (= (Ia-1) alkoxysilanes of partially substd. (methoxyacetic) (2-methoxyethoxy) (methyl)(phenylpropionic) silane (Va- 1) (=Ia-1) and generates a total substd. alkylalkoxy silane yield (Va-1: Va-2 = 74:26)of total 68percent, (refer to Table 1) in the part substituted alkoxysilane substd. (Ia-1) 12 50percent of the yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Amberlyst 15; at 110℃; for 0.0833333h;Microwave irradiation; | 10096] A mixture of 1.65 mmol of <strong>[3027-21-2]methylphenyldi(methoxy)silane</strong> (Ia), 6.6 mmol of butanol (ha) and 5 mg of CBV 780 (by Zeolyst International) was charged into a reaction tube, with stirring for 1 minute at room temperature (23° C.). The resulting product was analyzed using a gas chromatograph and a gas chromatographlmass spectrometer. The results revealed that a mixture of butoxysilane (lila) (lila-i:methylphenyl(methoxy)(butoxy)silane and IIIa-2: methylphenyldi(butoxy)silane, lila-i :IIIa-2=90: 10) had been generated with a yield of 88.5percent (see Table 1).10097] Reactions and analyses were carried out in the sameway as in Example 1, but modi1,?ing reaction conditions(starting materials, catalysts, temperature, time and so forth).The results of measurements of product yields are given inTable 1. | |
With CBV720; at 110℃; for 0.0833333h;Microwave irradiation; | 10096] A mixture of 1.65 mmol of <strong>[3027-21-2]methylphenyldi(methoxy)silane</strong> (Ia), 6.6 mmol of butanol (ha) and 5 mg of CBV 780 (by Zeolyst International) was charged into a reaction tube, with stirring for 1 minute at room temperature (23° C.). The resulting product was analyzed using a gas chromatograph and a gas chromatographlmass spectrometer. The results revealed that a mixture of butoxysilane (lila) (lila-i:methylphenyl(methoxy)(butoxy)silane and IIIa-2: methylphenyldi(butoxy)silane, lila-i :IIIa-2=90: 10) had been generated with a yield of 88.5percent (see Table 1).10097] Reactions and analyses were carried out in the sameway as in Example 1, but modi1,?ing reaction conditions(starting materials, catalysts, temperature, time and so forth).The results of measurements of product yields are given inTable 1. | |
With CBV600; at 110℃; for 0.0833333h;Microwave irradiation; | General procedure: di(methoxy)(methyl)(phenyl) silane (IIIa) 1.6mmol, 2-methoxyethanol (IVa) 3.2mmol, CBV780 (Zeolyst Co., Ltd.) 5 mg of the mixture in the reaction tube, 10 minutes at room temperature (25 °C ). An analysis result of a product gas chromatograph (GC), gas chromatograph/mass spectrometer (GC-MS), in nuclear magnetic resonance spectrum analyzer (NMR)and, as a product, di(2-methoxyethoxy)silane(phenyl)(methyl) (Va-2) (= (Ia-1) alkoxysilanes of partially substd. (methoxyacetic) (2-methoxyethoxy) (methyl)(phenylpropionic) silane (Va- 1) (=Ia-1) and generates a total substd. alkylalkoxy silane yield (Va-1: Va-2 = 74:26)of total 68percent, (refer to Table 1) in the part substituted alkoxysilane substd. (Ia-1) 12 50percent of the yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With Amberlyst 15; at 100℃; for 0.333333h;Microwave irradiation; Inert atmosphere; | 10263] A mixture of 3.3 mmolof<strong>[3027-21-2]methylphenyldi(methoxy)silane</strong> (Ia), 8.3 mmol of octanol (lie) and 10 mg of Amberlyst 15 (by Dow Chemical) was charged into a reaction tube, with stirring for 20 minutes at 100° C., using a microwave irradiation device (Discover by CEM Corporation), under a stream of nitrogen gas at a flow rate of 70 mE/minute, in an open system. The resulting product was post-processed and distilled in the same way as in Example 101. As a result there were obtained 2.8 mmol (yield 85percent) of methylphenyldi (octoxy)silane (IIIe-2).10264] The physical property values, spectral data and so forth of (IIIe-2) were as follows.10265] Boiling point: 165-175° C./0.6 mmHg (distillation temperature in short-path distillation)10266] Element analysis: C, 73.32; H, 11.21 (measured value); C, 72.95; H, 11.18 (calculated value C23H42O2Si);j0267] ?H-NMR (CDC13): oe 0.34 (s, 3H, SiCH3), 0.88 (t, J=7.i Hz, 6H, CCH3), 1.20-1.37 (m, 20H, OCC(CH2)5), 1.57 (quint, J=7.i Hz, 4H, OCCH2), 3.68-3.76 (m, 4H, OCH2), 7.35-7.43 (m, 3H, aromatic ring H), 7.60-7.65 (m, 2H, aromatic ring H)j0268] ?3C-NMR (CDC13): oe ?4.3, 14.1, 22.7, 25.8, 29.3, 29.4, 31.8, 32.6, 63.0, 127.8, 129.9, 134.0, 135.0j0269] 29Si-NMR (CDC13): oe ?18.0j0270] IR(liquidfilm): 1467,1429,1257,1121,1093,850,800, 778, 736, 699, 483, 437 cm?10271] GC-MS (El, 70 cv): mlz (relative intensity) 363(M-Me, 100), 300 (16), 285 (28), 243 (16), 139 (56), 137(56), 91(23), 77 (18), 69 (56), 57 (17), 55 (26), 43 (36), 41(36) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With rhodium(III) chloride trihydrate; copper diacetate; In N,N-dimethyl-formamide; at 90℃; under 760.051 Torr; for 10h;Sealed tube; | AddN-pyrimidinylpurine 1a (0.2 mmol), RhCl3•3H2O (0.004 mmol), Cu(OAc)2(0.4 mmol) andoctan-1-ol 2n (1.0 mmol) to 2.0 mL of DMF. after three times replacement of the carbon monoxide in the Young's tube, charged withcarbon monoxide (1 atm), the reaction and after 90 deg.] C oil bath for 10 hours, the reaction was stopped until the reaction was cooled to room temperature, was added acetic acidethyl ester and saturated brine several times Wash and extract.The organic phase was dried over anhydrous sodium sulfate and filtered.The solvent was evaporated to dryness, andethyl acetate / petroleum ether (1:10 to 1:1) was obtained.The product was a yellow oily liquid with ayield of 73%. |
Tags: 1-Octanol | Octanol | Aliphatic Chain Hydrocarbons | Alcohols | Aliphatic Acyl | Calcium Channel | Organic Building Blocks | Exosome | Neuronal Signaling | Lipids | Membrane Transporter/Ion Channel | 111-87-5
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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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