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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.
Synonyms: Ceryl Alcohol
4.5
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| CAS No. : | 506-52-5 |
| Formula : | C26H54O |
| M.W : | 382.71 |
| SMILES Code : | CCCCCCCCCCCCCCCCCCCCCCCCCCO |
| Synonyms : |
Ceryl Alcohol
|
| English Name : | 1-Hexacosanol |
| MDL No. : | MFCD00002940 |
| InChI Key : | IRHTZOCLLONTOC-UHFFFAOYSA-N |
| Pubchem ID : | 68171 |
* 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 |
|---|---|---|
| With hydrogen bromide at 150℃; | ||
| With phosphorus pentabromide at 200℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | With dicyclohexyl-carbodiimide In dichloromethane 1. 30 min, 0 deg C 2. 90 min, 25 deg C; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dicyclohexyl-carbodiimide In pyridine at 50 - 55℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 83% | With 2-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one In chloroform for 8h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With pyridinium chlorochromate | ||
| 4.97 g | With silica gel; pyridinium chlorochromate In dichloromethane at 25℃; for 20h; | 1.4; 1.1 Hexacosanal Add silica gel (5 g) and pyridinium chlorochromate (PCC) (5.63 g, 26.12 mmol) to a DCM solution (350 mL) ofhexacosan-1-ol (5 g, 13.06 mmol). Stir the mixture at 25°C for 20 h. Filter the reaction solution through diatomaceous earth,and concentrate the filtrate to obtain hexacosanal (4.97 g, 13.06 mmol), which is a white solid with no need for furtherpurification. 1H NMR (400 MHz, CDCl3) δ = 9.76 (s, 1H), 2.45 - 2.34 (m, 2H), 1.70 - 1.57 (m, 2H), 1.34 - 1.20 (m, 44H), 0.88 (t, J= 6.8 Hz, 3H). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogen In ethyl acetate at 25℃; |
[ 112-95-8 ]
[ 629-97-0 ]
[ 630-01-3 ]
[ 593-45-3 ]
[ 646-31-1 ]
[ 630-02-4 ]
[ 638-68-6 ]
[ 112-92-5 ]
[ 629-96-9 ]
[ 593-50-0 ]
[ 661-19-8 ]
[ 506-51-4 ]
[ 506-52-5 ]
[ 557-61-9 ]| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 12.4% 2: 13.4% 3: 7.8% 4: 3.2% 5: 1% 6: 0.2% 7: 0.05% | Stage #1: icosane; n-docosane; n-hexacosane; octadecane; tetracosane; octacosane; n-triacontane With oxygen at 30 - 50℃; for 3h; Stage #2: With sulfuric acid; water |
[ 112-95-8 ]
[ 629-97-0 ]
[ 630-01-3 ]
[ 629-50-5 ]
[ 593-45-3 ]
[ 646-31-1 ]
[ 630-02-4 ]
[ 638-68-6 ]
[ 112-92-5 ]
[ 629-96-9 ]
[ 593-50-0 ]
[ 661-19-8 ]
[ 506-51-4 ]
[ 506-52-5 ]
[ 557-61-9 ]| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 17.66% 2: 19.46% 3: 13.62% 4: 6.93% 5: 2.04% 6: 0.48% 7: 0.1% | Stage #1: icosane; n-docosane; n-hexacosane; octadecane; tetracosane; octacosane; n-triacontane With oxygen at 30 - 50℃; for 0.5h; Stage #2: Tridecane With titanium(IV) isopropylate at 30 - 50℃; for 6.86667h; Stage #3: With sulfuric acid; water at 80℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 1-methyl-1H-imidazole; 1-(mesitylene-2-sulfonyl)-3-nitro-1H-1,2,4-triazole In dichloromethane at 20℃; for 25h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 93% | With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18.5h; Inert atmosphere; | 5 Hexacosyl oleate. To a solution of commercially available 1-hexacosanol (0.03 g, 1 equiv.) in dry CH2Cl2(2.5 ml) and pyridine (1 ml) under argon atmosphere was added DMAP (0.01 g, 1 equiv.) and EDC×HCl (0.0380 g, 2.5 equiv.). Oleic acid (0.027 g in 0.5 ml dry CH2Cl2; 1.2 equiv.) was added dropwise. The resulting mixture was stirred o/n at rt. The reaction mixture was quenched after 18.5 h with H2O (5 ml) and diluted with CH2Cl2 (10 ml). The organic phase was separated and the aqueous layer extracted with CH2Cl2 (3 x 10 ml). The combined organic layers were washed with H2O (2 x 20 ml), dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (Hexane:EtOAc 95:5) and dried on the vacuum line to give the title compound as a white waxy solid (0.047 g, 93% yield). Mp 47.0-49.0 °C.1H NMR (500.13 MHz, CDCl3, 25 °C): 5.35 (dtt, 1H), 5.33 (dtt, 1H), 4.05 (t, 2H), 2.29 (t, 2H), 2.01 (ddt, 2H), 2.00 (ddt, 2H), 1.62 (tt, 2H), 1.60 (tt, 2H), 1.38-1.19 (m, 66H), 0.88 (t, 3H) and 0.88 (t, 3H) ppm.13C NMR (125.68 MHz, CDCl3): 13C NMR (125.68 MHz, CDCl3, 25 °C): 174.1, 130.1, 129.9, 64.5, 39.2, 34.6, 32.1-32.0, 29.9- 29.7, 29.5-29.4, 29.3-29.2, 28.8, 27.4-27.3, 26.1, 25.2, 22.8 and 14.3 ppm. HRMS m/z calculated for C44H86O2Na [M + Na]+669.6528, found 669.6693. |
| 93 % | With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; | 4 Hexacosyl oleate Hexacosyl oleate. To a solution of commercially available 1-hexacosanol (0.03 g, 1 equiv.) in dry CH2CI2 (2.5 ml) and pyridine (1 ml) under argon atmosphere was added DMAP (0.01 g, 1 equiv.) and EDC-HCI (0.0380 g, 2.5 equiv.). Oleic acid (0.027 g in 0.5 ml dry CH2CI2; 1.2 equiv.) was added dropwise. The resulting mixture was stirred o/n at rt. The reaction mixture was quenched after 18.5 h with H2O (5 ml) and diluted with CH2CI2 (10 ml). The organic phase was separated and the aqueous layer extracted with CH2CI2 (3 10 ml). The combined organic layers were washed with H2O (2 20 ml), dried over Na2S04, filtered and concentrated. The crude product was purified by column chromatography (Hexane: EtOAc 95:5) and dried on the vacuum line to give the title compound as a white waxy solid (0.047 g, 93% yield). Mp 47.0- 49.0 °C. NMR (500.13 MHz, CDCb): d 5.35 (dtt, 1H), 5.33 (dtt, 1H), 4.05 (t, 2H),2.29 (t, 2H), 2.01 (ddt, 2H), 2.00 (ddt, 2H), 1.62 (tt, 2H), 1.60 (tt, 2H), 1.38-1.19 (m, 66H), 0.88 (t, 3H) and 0.88 (t, 3H) ppm. 13C NMR (125.68 MHz, CDCb): d 13C NMR (125.68 MHz, CDCb): d 174.1, 130.1, 129.9, 64.5, 39.2, 34.6, 32.1-32.0, 29.9-29.7, 29.5-29.4, 29.3-29.2, 28.8, 27.4-27.3, 26.1, 25.2, 22.8 and 14.3 ppm. HRMS (El) m/z calculated for C44Hss02Na [M + Na]+ 669.6528, found 669.6693. |
| 93 % | With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; | 4 Hexacosyl oleate Hexacosyl oleate. To a solution of commercially available 1-hexacosanol (0.03 g, 1 equiv.) in dry CH2CI2 (2.5 ml) and pyridine (1 ml) under argon atmosphere was added DMAP (0.01 g, 1 equiv.) and EDC-HCI (0.0380 g, 2.5 equiv.). Oleic acid (0.027 g in 0.5 ml dry CH2CI2; 1.2 equiv.) was added dropwise. The resulting mixture was stirred o/n at rt. The reaction mixture was quenched after 18.5 h with H2O (5 ml) and diluted with CH2CI2 (10 ml). The organic phase was separated and the aqueous layer extracted with CH2CI2 (3 10 ml). The combined organic layers were washed with H2O (2 20 ml), dried over Na2S04, filtered and concentrated. The crude product was purified by column chromatography (Hexane: EtOAc 95:5) and dried on the vacuum line to give the title compound as a white waxy solid (0.047 g, 93% yield). Mp 47.0- 49.0 °C. NMR (500.13 MHz, CDCb): d 5.35 (dtt, 1H), 5.33 (dtt, 1H), 4.05 (t, 2H),2.29 (t, 2H), 2.01 (ddt, 2H), 2.00 (ddt, 2H), 1.62 (tt, 2H), 1.60 (tt, 2H), 1.38-1.19 (m, 66H), 0.88 (t, 3H) and 0.88 (t, 3H) ppm. 13C NMR (125.68 MHz, CDCb): d 13C NMR (125.68 MHz, CDCb): d 174.1, 130.1, 129.9, 64.5, 39.2, 34.6, 32.1-32.0, 29.9-29.7, 29.5-29.4, 29.3-29.2, 28.8, 27.4-27.3, 26.1, 25.2, 22.8 and 14.3 ppm. HRMS (El) m/z calculated for C44Hss02Na [M + Na]+ 669.6528, found 669.6693. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With zinc(II) oxide at 80 - 180℃; | 4.i Step (i): Initially, 19.10 grams of n-hexcosanol were placed in a 100 mL flask and melted at 80° C. Subsequently, 4.50 grams of methyl glycolate, along with 0.018 grams of zinc oxide, were added into the flask. The mixture in the flask was stirred under atmospheric pressure, and the temperature was gradually raised to 180° C. to facilitate the evaporation of methanol. The reaction was terminated when no further methanol was observed to evaporate. The resulting light yellow liquid in the flask was identified as hexcosyl glycolate. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: C21H28ClCoN3(1+)*Cl(1-); potassium <i>tert</i>-butylate / toluene / 12 h / 100 °C / Inert atmosphere 2: C21H28ClCoN3(1+)*Cl(1-); potassium <i>tert</i>-butylate / toluene / 12 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium <i>tert</i>-butylate; C21H28ClCoN3(1+)*Cl(1-) In toluene at 100℃; for 12h; Inert atmosphere; |