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CAS No. : | 624-08-8 | MDL No. : | MFCD00046734 |
Formula : | C17H36O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WTWWTKPAEZQYPW-UHFFFAOYSA-N |
M.W : | 256.47 | Pubchem ID : | 136435 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 1.0 |
Num. rotatable bonds : | 14 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 84.99 |
TPSA : | 20.23 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -2.52 cm/s |
Log Po/w (iLOGP) : | 4.72 |
Log Po/w (XLOGP3) : | 7.53 |
Log Po/w (WLOGP) : | 5.85 |
Log Po/w (MLOGP) : | 4.7 |
Log Po/w (SILICOS-IT) : | 5.92 |
Consensus Log Po/w : | 5.74 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.25 |
Solubility : | 0.00144 mg/ml ; 0.00000562 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -7.79 |
Solubility : | 0.00000416 mg/ml ; 0.0000000162 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -5.8 |
Solubility : | 0.000407 mg/ml ; 0.00000159 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.4 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 - 20℃; for 1h; | To a solution of 25 g tridecane-7-one (1 eq) dissolved in MeOH/THF, 1.5 eq. sodium borohydride was added at 0 C. and the resulting solution was stirred at room temperature for 1 hour. Progress of the reaction was monitored by TLC (10% EtOAc in hexane; Rf: 0.5). Reaction mass was quenched with saturated NH4Cl solution (75 ml). Solvent was removed under reduced pressure and the resulting crude was portioned between EtOAc(150 ml) and water (100 ml). Organic layer was separated and the aqueous layer was washed with EtOAc (3×100 ml). Combined organic layers were concentrated under reduced pressure to get white solid. Quantity produced, 22 g; yield, 90%. |
90% | With methanol; sodium tetrahydroborate; In tetrahydrofuran; at 0 - 20℃; for 1h; | To a solution of 25 g tridecane-7-one (1 eq) dissolved in MeOH/THF, 1.5 eq. sodium borohydride was added at 0 C. and the resulting solution was stirred at room temperature for 1 hour.Progress of the reaction was monitored by TLC (10% EtOAc in hexane; Rf: 0.5). Reaction mass was quenched with saturated NH4Cl solution (75 ml). Solvent was removed under reduced pressure and the resulting crude was portioned between EtOAc(150 ml) and water (100 ml). Organic layer was separated and the aqueous layer was washed with EtOAc (3×100 ml). Combined organic layers were concentrated under reduced pressure to get white solid. Quantity produced, 22 g; yield, 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Heptadecan-9-ol (2): In a 250 mL three neck flame-dried,magnesium turnings (2.21 g, 91 mmol) was put into dry diethylether(60 mL). After 30 min a solution of bromooctane (15 mL,87 mmol) in diethylether (45 mL)was then added dropwise and the reaction mixture was allowed to stir for 1 more hour. Finally, a solution of ethyl formate (3 mL, 37.1 mmol) was added dropwise and stirred at room temperature overnight. The reaction mixture was poured in water (300 mL) and extracted 3 times with 150 mL of ethyl acetate, dried over magnesium sulfate and the solvent was removed under vacuum to give a white solid which was used for the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triethylamine; In dichloromethane; for 2h; | 9-Heptadecane p-Toluenesulfonate (3): p-toluenesulfonyl chloride (14.7 g, 77 mmol) in CH2Cl2 (60 mL) was added dropwise to a solution of <strong>[624-08-8]heptadecan-9-ol</strong> (2) (18.00 g, 70 mmol) and triethylamine (Et3N) (24.4 mL, 181 mmol) in CH2Cl2 (90 mL) in a dry 250 mL flask. The mixture was stirred for 2 h, 250 mL of water was added, and the mixture was extracted three times with CH2Cl2 (3 * 150 mL). ;The organic phase was washed with water, dried (Na2SO4), and concentrated under reduced pressure. The crude product was purified by silica-gel flash chromatography (cyclohexane-ethyl acetate, 95-5 as eluent) to give 22.5 g of colorless oil, which crystallized as the title product (yield: 78%). 1H NMR (400 MHz, CDCl3): delta (ppm) 7.78 (d, J = 8.3 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H), 4.54 (p, J = 6.0 Hz, 1H), 2.43 (s, 3H), 1.55 (m, 4H), 1.21 (m, 24H), 0.88 (t, 6H). 13C NMR (101 MHz, CDCl3): delta (ppm) 144.38, 134.97, 129.74, 127.85, 84.78, 70.82, 34.26, 31.97, 29.48, 29.42, 29.28, 24.81, 22.78, 21.71, 14.23. FT-IR (ATR): nu = 2954, 2923, 2852, 1598, 1521, 1495, 1465, 1354, 1305, 1173, 1097, 1020, 895, 816, 766, 720, 662, 575, 554 cm-1. |
64% | With triethylamine; In dichloromethane; at 0℃; for 1.5h; | From 0 C in a round flask was added the p- toluenesulfonyl chloride (5.5g) and the mixture was stirred and then placed in methylene chloride (150mL). Put Then, hepta-decane-9-ol followed by the addition of (5g) and slowly diluted in methylene chloride (5mL), triethylamine (7mL) and triethylamine hydrochloride (3.71g), and the mixture was stirred for 90 minutes . MC and the organic layer with brineAnd then extracted to remove the remaining water over anhydrous magnesium sulfate, and after evaporation of the solvent was recrystallized from a MC and MeOH to give the Heptadecane-9-yl 4-methlybenzenesulfornate (compound f-4) as a white solid (yield: 64% ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; trimethylamine; In water; toluene; benzene; | PRODUCTION EXAMPLE 11 (1-Octyl)nonyl 2-trimethylammonioethyl phosphate <strong>[624-08-8]9-Heptadecanol</strong> (2.56 g, 10 mmol) and bromoethyl phosphorodichloridate (4.11 g, 17 mmol) were dissolved in dry benzene (20 ml). To the solution was added dropwise dry pyridine (1.34 g, 17 mmol) under stirring. The mixture was stirred at room temperature for three hours, then to which was added water. The mixture was again stirred for thirty minutes at 80 C. The solvent was evaporated off, and the residue was dissolved in ether. The ether solution was washed with water, and then concentrated to dryness. The residue was dissolved in toluene (25 ml) containing trimethylamine (5 g), and the solution was left standing for three days. The reaction solution was concentrated under reduced pressure. The residue was subjected to a silica-gel chromatography [eluent: chloroform-methanol-water (65:25:4 by volume)] to yield 0.76 g of the object compound as colorless solid matter. IR(KBr)cm-1: 2925, 2860, 1465, 1380, 1230, 1085, 970, 760. NMR(90 MHz, CDCl3)delta: 0.87(t, 6H), 1.24(m, 28H), 3.37(s, 9H), 3.79(br, 2H), 4.0-4.4(br, 3H). Elemental Analysis: C22 H48 NO4 P*0.5H2 O. Calcd.: C, 61.37; H, 11.47; N, 3.25; P, 7.19. Found: C, 61.59; H, 11.68; N, 3.37; P, 7.26. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.2% | With di-isopropyl azodicarboxylate; triphenylphosphine; In diethyl ether; at 20℃;Inert atmosphere; | A solution of 1 (10 g, 39 mmol), triphenylphosphine (10.22 g, 39 mmol), and phthalimide (5.74 g, 39 mmol) in dry diethyl ether (60 mL) was purged with N2, and a solution of DIAD (7.70 mL, 39 mmol) in dry diethyl ether (30 mL) was added slowly. After stirring overnight, the precipitate was filtered off, and then washed thoroughly with diethyl ether. After removal of the solvent by rotary evaporator, the crude product was purified by column chromatography (silica) using hexane/dichloromethane (9:1) as an eluent to give a viscous and colorless oil (10.85 g, 72.2%). 1H NMR (300 MHz, CDCl3), delta (ppm): 7.82 (dd, J=3.3, 5.7 Hz, 2H), 7.70 (dd, J=3.0, 5.4 Hz, 2H), 4.21-4.14 (m, 1H), 2.10-1.99 (m, 2H), 1.78-1.64 (m, 2H), 1.25-1.26 (m, 24H), 0.84 (t, J=6.3 Hz, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.3% | A solution of ethyl formate (10 g, 135 mmol) in dry THF (80 mL) was added dropwise to a fresh solution of octyl magnesium bromide, which was prepared from 1-bromooctane (58 g, 300 mmol) and magnesium (8.15 g, 340 mmol) in 150 mL dry THF. After then, the reaction mixture was stirred overnight at room temperature. Next, the reaction mixture was quenched by the addition of MeOH, followed by saturated aqueous NH4Cl. The crude compound was extracted three times with ethyl acetate. The combined organic fractions were washed with brine and dried over MgSO4. After removal of the solvent, the residue was purified by recrystalization from acetonitrile to afford heptadecane-9-ol (1) as white solids (30.91 g, 89.3%). 1H NMR (300 MHz, CDCl3), delta (ppm): 3.58 (m, 1H), 1.43-1.25 (m, 29H), 0.88 (t, J=6.6 Hz, 6H). | |
64% | With magnesium; In ethylene dibromide; | Insert the round Mg powder in the last sample condenser is mounted makes the vacuum. Then, after taking up the activation of the Mg through the vacuum of 1,2-dibromoethane, to slowly inject the octylbromide 43.3mL makes the R-MgBr. Then, it gives to slowly inject 10mL ethyl formate. After completion of the reaction through a sulfuric acid solution, after extraction via the ether and aqueous NaCl solution, when recrystallized by hexane extraction and the organic layer can be obtained through a white solid heptadecan-9-ol (compound f-3). (Yield: 64%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 3h; | To a 250 mL round flask was added compound 1 (4.43 g, 16.0 mmol), <strong>[624-08-8]heptadecan-9-ol</strong> (4.92 g, 19.2 mmol) and PPh3 (5.04 g, 19.2 mmol) were charged, and then 50 mL of tetrahydrofuran was injected. Diisopropyl azodicarboxylate (3.88 g, 19.2 mmol) was slowly added at 0 C and stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was fractionally distilled off through methylene chloride, and the remaining water was removed with anhydrous magnesium sulfate. The solvent was evaporated and purified by column chromatography to obtain 4,7-dibromo-5,6 2-heptadecan-9-yl) -2Hbenzo [d] [1,2,3] triazole (Compound 2). (Yield: 60%). 1H NMR (300 MHz, CDCl3, delta): 4.90 (m, 1H), 2.35 (m, 2H), 2.01 (m, 2H), 1.31-1.21 (m, 22H), 1.08-0.96 (m, 2H), 0.86 (t, 6H). 13C NMR (75 MHz, CDCl3, delta): 143.31, 129.22, 110.11, 69.54, 35.59, 31.75, 29.22, 29.14, 29.01, 26.05, 22.62, 14.16. Anal. Calcd for C23H37Br2N3: C, 53.60; H, 7.24; Br, 31.01; N, 8.15. Found: C, 53.80; H, 7.30; N, 8.10. |
50% | With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0℃; for 3h;Inert atmosphere; | Diisopropyl azodicarboxylate (0.77 g, 19.2 mmol) was added to a magnetically stirred solution of 1 (1.00 g, 16.0 mmol), <strong>[624-08-8]heptadecan-9-ol</strong> (1.00 g, 19.2 mmol), and triphenyl phosphine (1.00 g,19.2 mmol) in tetrahydrofuran (50 mL) at 0 C under nitrogen. After stirring for 3 h, the reaction mixture was poured into water (200 mL), and the product was extracted with diethyl ether. The organic layer was washed with brine, driedover anhydrous MgSO4, and concentrated under reduced pressure. The crude product was purified by column chromatographyand then crystallized from an isopropanol/hexane mixture to give compound 2 as colorless crystals (1.10 g, 50% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; | Example 58a: In a 500 ml round-bottom flask equipped with a stir bar, <strong>[624-08-8]9-heptadecanol</strong> (1.12 g, 4.37 mmol) was dissolved in DCM (30 ml). 4-(ferf-butoxy)-4-oxobutanoic acid (0.913 g, 5.24 mmol) and DMAP (0.107 g, 0.873 mmol) were added, followed by DIPEA (3.05 ml, 17.47 mmol). The mixture is stirred at rt for a minute before addition of EDC.HCI (1.172 g, 6.1 1 mmol). The mixture is then stirred at rt overnight. The mixture was concentrated under reduced pressure, and the concnetrate was purified on silica gel with ethyl acetate / heptane as eluent to provide the title compound. 1H NMR (400 MHz, CDCI3) delta = 4.89 (quin, J=6.27 Hz, 1 H), 2.48 - 2.65 (m, 4 H), 1.48 - 1.57 (m, 4 H), 1.42 - 1.48 (m, 9 H), 1 .18 - 1.38 (m, 24 H), 0.84 - 0.96 (m, 6 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; hexane; | Preparation of 5-(heptadecan-9-yl)-5H-dithieno[3,2-c:2',3'-e][1,2]thiazine 4,4-dioxide (6) The compound 6e was synthesized according to Scheme 2b below. Specifically, a 10 ml Schlenk flask was charged with a magnetic stirrer bar, sulfonamide 1 (123 mg, 0.5 mmol), <strong>[624-08-8]heptadecan-9-ol</strong> (153.9 mg, 0.6 mmol, 1.2 equiv) and triphenylphosphine (157.2, 0.6 mmol, 1.2 equiv). The flask was evacuated and backfilled with N2 3 times and 10 ml of dry THF was added. The mixture was cooled down to 0 C. Then, a solution of diisopropyl azodicarboxylate (DIAD, 123 mg 0.6 mmol, 1.2 equiv) in 2 ml of THF was slowly added (over 1 h) to the reaction mixture. The reaction mixture was stirred at 0 C. for 2 h, after which it was allowed to warm up to room temperature and stirred at this temperature for 12 h. Then, the mixture was diluted with H2O and extracted with diethyl ether, then dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified via column chromatography on silica gel using a 1:1 hexane/DCM mixture as the eluent to afford the product 6e (127 mg, 0.27 mmol) as a colorless viscous oil at 53% yield. 1H NMR (499 MHz, CDCl3) delta 7.30-7.34 (m, 2H), 7.29 (d, J=5.3 Hz, 1H), 7.09 (d, J=5.4 Hz, 1H), 4.23-4.33 (m, 1H), 1.60-1.79 (m, 2H), 1.47-1.58 (m, 2H), 1.01-1.30 (m, 24H), 0.84 (t, J=7.1 Hz, 6H). 13C NMR (101 MHz, CDCl3) delta 136.37, 130.14, 124.56, 124.34, 122.01, 121.66, 34.41, 31.79, 29.26, 29.02, 26.26, 22.59, 14.07. Some signals may overlap. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 15h;Schlenk technique; Inert atmosphere; | Specifically, a 10 ml Schlenk flask was charged with a magnetic stirrer bar, sulfonamide 1 (123 mg, 0.5 mmol), <strong>[624-08-8]heptadecan-9-ol</strong> (153.9 mg, 0.6 mmol, 1.2 equiv) and triphenylphosphine (157.2, 0.6 mmol, 1.2 equiv). The flask was evacuated and backfilled with N2 3 times and 10 ml of dry THF was added. The mixture was cooled down to 0 C. Then, a solution of diisopropyl azodicarboxylate (DIAD, 123 mg 0.6 mmol, 1.2 equiv) in 2 ml of THF was slowly added (over 1 h) to the reaction mixture. The reaction mixture was stirred at 0 C. for 2 h, after which it was allowed to warm up to room temperature and stirred at this temperature for 12 h. Then, the mixture was diluted with -H2O and extracted with diethyl ether, then dried over -Na2SO4. The solvent was removed under reduced pressure and the residue was purified via column chromatography on silica gel using a 1:1 hexane/DCM mixture as the eluent to afford the product 6e (127 mg, 0.27 mmol) as a colorless viscous oil at 53% yield. 1H NMR (499 MHz, -CDCl3) delta 7.30-7.34 (m, 2H), 7.29 (d, J=5.3 Hz, 1H), 7.09 (d, J=5.4 Hz, 1H), 4.23-4.33 (m, 1H), 1.60-1.79 (m, 2H), 1.47-1.58 (m, 2H), 1.01-1.30 (m, 24H), 0.84 (t, J=7.1 Hz, 6H). 13C NMR (101 MHz, -CDCl3) delta 136.37, 130.14, 124.56, 124.34, 122.01, 121.66, 34.41, 31.79, 29.26, 29.02, 26.26, 22.59, 14.07. Some signals may overlap. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 3h; | A 250mL round bottom flask 4,7-dibromo -2H- benzo [1,2,3] triazole (Compound i-2) 4.43g, <strong>[624-08-8]heptadecan-9-ol</strong> 4.92g, after inserting the respective PPh3 5.04g, vacuum the makes. Thereafter, the THF anhydours 100mL injected, slowly inject diisopropylazodicarboxylate 3.88g under ice-base. 3 hours of stirring, through the water to terminate the reaction, and after extraction via the ether, the product clean colorlesscrystal 4,7-dibromo-2- (hepka decan-9-yl) -2H- benzo through a column chromatography [d ] [2,3] to give the triazole (compound i-3). (Yield: 50%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h; | To a solution of 8-bromooctanoic acid (1.04 g, 4.6 mmol) and <strong>[624-08-8]heptadecan-9-ol</strong> (1.5 g, 5.8 mmol) in dichloromethane (20 mL) was added N-(3-dimethylaminopropyl)-N- ethylcarbodiimide hydrochloride (1.1 g, 5.8 mmol), NN-diisopropylethylamine (3.3 mL, 18.7 mmol) and DMAP (114 mg, 0.9 mmol). The reaction was allowed to stir at rt for 18 h. The reaction was diluted with dichloromethane and washed with saturated sodium bicarbonate. The organic layer was separated and washed with brine, and dried over MgSC The organic layer was filtered and evaporated in vacuo. The residue was purified by silica gel chromatography (0- 10% ethyl acetate in hexanes) to obtain heptadecan-9-yl 8-bromooctanoate (875 mg, 1.9 mmol, 41%). XH NMR (300 MHz, CDC13) delta: ppm 4.89 (m, 1H); 3.42 (m, 2H); 2.31 (m, 2H); 1.89 (m, 2H); 1.73-1.18 (br. m, 36H); 0.88 (m, 6H). |
41% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h; | To a solution of 8-bromooctanoic acid ( 1 .04 g, 4.6 mmol) and <strong>[624-08-8]heptadecan-9-ol</strong> ( 1 .5 g, 5.8 mmol) in dichloromethane (20 mL) was added N-(3-dimethylaminopropyl)-N'- ethylcarbodiimide hydrochloride (1 .1 g, 5.8 mmol), N,N-diisopropylethylamine (3.3 mL, 1 8.7 mmol) and DMAP ( 1 14 mg, 0.9 mmol). The reaction was allowed to stir at rt for 1 8 h. The reaction was diluted with dichloromethane and washed with saturated sodium bicarbonate. The organic layer was separated and washed with brine, and dried over MgS04. The organic layer was filtered and evaporated in vacuo. The residue was purified by silica gel chromatography (0- 10% ethyl acetate in hexanes) to obtain heptadecan-9-yl 8- bromooctanoate (875 mg, 1 .9 mmol, 41 %). N MR (300 M Hz, CDCI3) delta: ppm 4.89 (m, 1 H); 3.42 (m, 2H); 2.3 1 (m, 2H); 1 .89 (m, 2H); 1 .73- 1 . 1 8 (br. m, 36H); 0,88 (m, 6H). |
41% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h; | Step 1 : Heptadecan-9- -bromooctanoate [00862] To a solution of 8-bromooctanoic acid (1.04 g, 4.6 mmol) and <strong>[624-08-8]heptadecan-9-ol</strong> (3223) (1.5 g, 5.8 mmol) in dichloromethane (20 mL) was added N-(3-dimethylaminopropyl)-N- ethylcarbodiimide hydrochloride (1.1 g, 5.8 mmol), NN-diisopropylethylamine (3.3 mL, 18.7 mmol) and DMAP (114 mg, 0.9 mmol). The reaction was allowed to stir at room temperature for 18 h. The reaction was diluted with dichloromethane and extracted with saturated sodium bicarbonate. The organic layer was separated, washed with brine and dried over MgSC The organic layer was filtered and the filtrate was evaporated in vacuo. The residue was purified by silica gel chromatography (0-10% ethyl acetate in hexanes) to obtain heptadecan-9-yl 8- bromooctanoate (875 mg, 1.9 mmol, 41%). (3224) lH NMR (300 MHz, CDC13) delta: ppm 4.89 (m, 1H); 3.42 (m, 2H); 2.31 (m, 2H); 1.89 (m, 2H); 1.73-1.18 (br. m, 36H); 0.88 (m, 6H). |
41% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h; | To a solution of 8-bromooctanoic acid (1.04 g, 4.6 mmol) and <strong>[624-08-8]heptadecan-9-ol</strong> (1.5 g, 5.8 mmol) in dichloromethane (20 mL) was added N-(3-dimethylaminopropyl)- N?-ethylcarbodiimide hydrochloride (1.1 g, 5.8 mmol), N,N-diisopropylethylamine (3.3 mL, 18.7 mmol) and DMAP (114 mg, 0.9 mmol). The reaction was allowed to stir at rt for 18 h. The reaction was diluted with dichloromethane and washed with saturated sodium bicarbonate. The organic layer was separated and washed with brine, and dried over MgSO4. The organic layer was filtered and evaporated in vacuo. The residue was purified by silica gel chromatography (0-10% ethyl acetate in hexanes) to obtain heptadecan-9-yl 8-bromooctanoate (875 mg, 1.9 mmol, 4 1%).107201 ?HNMR (300 IVIFIz, CDC13) : ppm 4.89 (m, 1H); 3.42 (m, 2H); 2.31 (m, 2H);1.89 (m, 2H); 1.73-1.18 (br. m, 36H); 0.88 (m, 6H). |
41% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h; | To a solution of 8-bromooctanoic acid (1.04 g, 4.6 mmol) and <strong>[624-08-8]heptadecan-9-ol</strong> (1.5 g, 5.8 mmol) in dichloromethane (20 mL) was added N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (1.1 g, 5.8 mmol), N,N-diisopropylethylamine (3.3 mL, 18.7 mmol) and DMAP (114 mg, 0.9 mmol). The reaction was allowed to stir at rt for 18 h. The reaction was diluted with dichloromethane and washed with saturated sodium bicarbonate. The organic layer was separated and washed with brine, and dried over MgSO4. The organic layer was filtered and evaporated in vacuo. The residue was purified by silica gel chromatography (0-10% ethyl acetate in hexanes) to obtain heptadecan-9-yl 8-bromooctanoate (875 mg, 1.9 mmol, 41%).1H NMR (300 MHz, CDCl3) : ppm 4.89 (m, 1H); 3.42 (m, 2H); 2.31 (m, 2H); 1.89 (m, 2H); 1.73-1.18 (br. m, 36H); 0.88 (m, 6H). |
41% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h; | To a solution of 8-bromooctanoic acid (1.04 g, 4,6 mmol) and <strong>[624-08-8]heptadecan-9-ol</strong> (1.5 g, 5.8 mmol) in dichloromethane (20 rnL) was added N-(3 dimethylaminopropyl)APethylcarbodiimide hydrochloride (1.1 g, 5.8 mmoi), AN-diisopropylethylarnine (3.3 mL, 18.7 rnmoi) and DMAP (114 mg, 0.9 mmol). The reaction was allowed to stir at rt for 18 h. The reaction was diluted with dichioromethane and washed with saturated sodium bicarbonate. The organic layer was separated and washed with brine, and dried over MgSO4. The organic layer was filtered and evaporated in vacuo. The residue was purified by silica gel chromatography (0-10% ethyl acetate in hexanes) to obtain heptadecan-9-yl 8-bromooctanoate (875 mg, 1.9 mmol, 41%).?H N]?[R (300 MHz, CDCI3) ppm 4.89 (in, 11-1); 342 (m, 2EI) 2.31 (in, 21-1); 189 (m, 2E{) 1.73-1.18 (br. m, 36H); 0.88 (in, 6H). |
41% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h; | [1111] To a solution of 8-bromooctanoic acid (1.04 g, 4.6 mmol) and <strong>[624-08-8]heptadecan-9-ol</strong> (1.5 g, 5.8 mmol) in dichloromethane (20 mL) was added N-(3-dimethylaminopropyl)-N- ethylcarbodiimide hydrochloride (1.1 g, 5.8 mmol), N,N-diisopropylethylamine (3.3 mL, 18.7 mmol) and DMAP (114 mg, 0.9 mmol). The reaction was allowed to stir at rt for 18 h. The reaction was diluted with dichloromethane and washed with saturated sodium bicarbonate. The organic layer was separated and washed with brine, and dried over MgSO4. The organic layer was filtered and evaporated in vacuo. The residue was purified by silica gel chromatography (0- 10% ethyl acetate in hexanes) to obtain heptadecan-9-yl 8-bromooctanoate (875 mg, 1.9 mmol, 41%). [1112] 1H NMR (300 MHz, CDCl3) : ppm 4.89 (m, 1H); 3.42 (m, 2H); 2.31 (m, 2H); 1.89 (m, 2H); 1.73-1.18 (br. m, 36H); 0.88 (m, 6H). |
41% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 18h; | [0030] To a solution of 8-bromooctanoic acid (1.04 g, 4.6 mmol) and <strong>[624-08-8]heptadecan-9-ol</strong> (1.5 g, 5.8 mmol) in dichloromethane (20 mL) was added N-(3-dimethy laminopropy-N7- ethylcarbodiimide hydrochloride (1.1 g, 5.8 mmol), N,N-diisopropylethylamine (3.3 mL, 18.7 mmol) and DMAP (1 14 mg, 0.9 mmol). The reaction was allowed to stir at rt for 18 h. The reaction was diluted with dichloromethane and washed with saturated sodium bicarbonate. The organic layer was separated and washed with brine, and dried over MgS04. The organic layer was filtered and evaporated in vacuo. The residue was purified by silica gel chromatography (0- 10% ethyl acetate in hexanes) to obtain heptadecan-9-yl 8-bromooctanoate (875 mg, 1.9 mmol, 41%). NMR (300 MHz, CDCb) delta: ppm 4.89 (m, 1H); 3.42 (m, 2H); 2.31 (m, 2H); 1.89 (m, 2H); 1.73-1.18 (br. m, 36H); 0.88 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 20h;Inert atmosphere; | A solution of nonanedioic acid (500 mg, 2.66 mmol), <strong>[624-08-8]heptadecan-9-ol</strong> (681 mg, 2.66 mmol) and DMAP (65 mg, 0.53 mmol) in DCM (13 mL) was treated with EDC HC1 (509 mg, 2.66 mmol). The reaction was allowed to stir at room temperature under nitrogen for 20 hours. Quenched reaction with H20 and extracted three times with DCM. Washed organic layers with saturated aqueous NaHC03 followed by 10% citric acid and brine. Dried organic layers over a2S04, filtered and concentrated in vacuo.' The residue was purified by silica gel chromatography (0-20% MeOH in DCM) to afford 9-(heptadecan-9-yloxy)-9-oxononanoic acid (350 mg, 1.05 mmol, 40%).UPLC/ELSD: RT = 3.49 min. MS (ES): m/z (MET) 425.0 for C26H50O4 'H NMR (300 MHz, CDCI3) delta: ppm 1 1 .02 (br. s, l H); 4.89 (m, I H); 2.33 (m, 4H); 1 .66- 1 .64 (br. m, 4H); 1 .53-1 .51 (br. m, 4H); 1 .35- 1.28 (br. m, 30H); 0.90 (m, 6H). |
Tags: 624-08-8 synthesis path| 624-08-8 SDS| 624-08-8 COA| 624-08-8 purity| 624-08-8 application| 624-08-8 NMR| 624-08-8 COA| 624-08-8 structure
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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 |
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