Structure of 72388-18-2
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| CAS No. : | 72388-18-2 |
| Formula : | C28H58O |
| M.W : | 410.76 |
| SMILES Code : | CCCCCCCCCCCCCCC(CCCCCCCCCCCC)CO |
| English Name : | 2-Dodecylhexadecan-1-ol |
| MDL No. : | MFCD27665210 |
| InChI Key : | DEMBLPGWNXUBIQ-UHFFFAOYSA-N |
| Pubchem ID : | 3018340 |
* 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 |
|---|---|---|
| 51% | With boron trifluoride diethyl etherate In dichloromethane at -20℃; for 3h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: 51 percent / BF3*Et2O / CH2Cl2 / 3 h / -20 °C 2: 91 percent / KOH / ethanol / 5 h / 50 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: 51 percent / BF3*Et2O / CH2Cl2 / 3 h / -20 °C 2: 91 percent / KOH / ethanol / 5 h / 50 °C 3: SOCl2 / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 90% | With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | With tripotassium phosphate tribasic; 5%-palladium/activated carbon In toluene at 220℃; for 288h; Sealed tube; | 14 Example 14 Guerbet Reaction of 1-Tetradecanol to C28-Alcohol_: Example 14Guerbet Reaction of 1-Tetradecanol to C28-Alcohol_:The Guerbet reaction was carried out in a 4560 mini Parr reactor. In a 50 mL reactor, 1- tetradecanol (10 g, 47 mmol), 5% palladium on carbon (containing 50% of water, 0.06 mg, 0.14 mmol), potassium phosphate tribasic (3.5 g, 16.5 mmol), toluene (15 mL) were added. The reaction vessel was sealed and the mixture was stirred at 220 °C for 6 days. The GC analysis of the crude mixture revealed that the mixture mainly consisted of C28-alcohol and unreacted starting material in 1 : 1 ratio. The reaction mixture was filtered over celite and was washed with EtOH. The solvent was evaporated and a new batch of 5% palladium on carbon (containing 50% of water, 0.06 mg, 0.14 mmol), potassium phosphate tribasic (3.5 g, 16.5 mmol), toluene (15 mL) were added. The reaction mixture was further stirred for 6 days. The mixture was filtered over celite to provide C28- OH in 75% overall yield. |
| 76 %Chromat. | With potassium-t-butoxide In neat (no solvent) at 150℃; for 24h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Cooling with ice; | 25 Preparation of 2-dodecylhexadecan-1-ol To the reaction flask was added THF (1 L), and lithium aluminum hydride (46 g, 1.2 mol) was added portionwise in an ice bath, and methyl 2-dodecylhexadecanoate (658 g, 1.5 mol) was slowly added dropwise. THF solution (200 mL). After the addition, the reaction was allowed to rise to room temperature for 2 hours. The reaction was quenched by slowly adding water under ice-cooling, and 6N hydrochloric acid was added to the solution to be clarified, and the aqueous phase was extracted three times with ethyl acetate.Wash with saturated sodium chloride and dry over anhydrous sodium sulfate. The solvent was evaporated under concentrated pressure and distilled under reduced pressure to give 520 g of 2-dodecylhexadecan-1-ol.The yield was 85%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 90% | With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 20℃; for 12h; | |
| 86% | With 1H-imidazole; carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 3h; Cooling with ice; | 26 Preparation of 1-bromo-2-dodecylhexadecane 2-Dodecylhexadecan-1-ol (411 g, 1.0 mol), imidazole (88 g, 1.3 mol), triphenylphosphine (341 g, 1.3 mol), dichloromethane (1.2 L) To the reaction flask, a solution of carbon tetrabromide (431 g, 1.3 mol) in dichloromethane (600 mL) was added dropwise under ice-cooling, and the mixture was slowly warmed to room temperature for 3 hours. The solvent was evaporated under reduced pressure, and the mixture was stirred and evaporated, evaporated, evaporated, and evaporated. After concentrated evaporation of solvent407 g of 1-bromo-2-dodecylhexadecane was obtained in a yield of 86%. |
| With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 50℃; | 7.1 (1) Under the catalytic conditions of EDC (314 mg, 1.64 mmol) and DMAP (33 mg, 0.27 mmol), meldonium (200 mg, 1.37 mmol) and 2-dodecylhexadecanol (468 mg, 1.14 mmol) are dissolved in 5 mL of DMF, and stirred and heated at 50°C for 12 h. The solvent is removed by rotary evaporation to separate the initial product, and purified by silica gel chromatography (product eluent: n-hexane: ethyl acetate = 1:1 (volume ratio)), and vacuum dried to obtain the product THP-1216. The reaction process is as follows: |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1.46 g | With tetrakis(2-ethylhexyl) orthotitanate In toluene at 50℃; for 24h; | 30 In a reaction container, 1.00 g (2.44 × 10 -3 mol) of the compound represented by the following formula (BG), 1.00 g of toluene, 0.550 g (2.68 × 10 -3 mol) of (3-isocyanatopropyl)trimethoxysilane and 6.88 × 10 -2 g (1.22 × 10 -4 mol) of tetra-2-ethylhexyl titanium were mixed and aged at 50°C for 24 hours. After that, the solvent and unreacted products were distilled off under reduced pressure to obtain 1.46 g of the product. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triethylamine In dichloromethane at 0℃; for 2h; | Synthesis of Ionizable Lipids. General procedure: A one pot, two step method was used to prepare a library of dozens of ionizable lipids: first, fatty alcohols with different structures were reacted with acryloyl chloride, with triethylamine added as an acid scavenger in a molar ratio of 1:3:3, and the reaction was carried out in dichloromethane at 0 °C for 2 hours, then the solvent and some impurities were removed by rotary evaporation. Next, amines with different structures were added in a molar ratio of 0.3, and the reaction was carried out in anhydrous ethanol at 50 °C for 24 hours. After the reaction was completed, the separation was performed by column chromatography (eluent hexane: ethyl acetate =3:1), and the desired ionizable lipids were obtained after rotary evaporation, vacuum drying, and structural characterization by nuclear magnetic resonance (NMR), and high performance liquid chromatography with an evaporative light scattering detector (HPLC ELSD). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 12h; | 6.1 (1) Glutaric anhydride (851 mg, 7.5 mmol) was slowly added to a pyridine solution (5 mL) of 2-dimethylaminoethanol (1 g, 11.2 mmol), stirred overnight, and the excess 2-dimethylaminoethanol and pyridine solution were removed by rotary evaporation to obtain the product organic acid B. Under the catalytic conditions of EDC (191 mg, 1.2 mmol) and DMAP (20 mg, 0.2 mmol), organic acid B (114 mg, 1 mmol) and 2-dodecylhexadecanol (205 mg, 0.5 mmol) were dissolved in 5 mL of CDCl2, stirred at room temperature for 12 h, and the solvent was removed by rotary evaporation to separate the initial product, which was purified by silica gel chromatography (product eluent: n-hexane: ethyl acetate = 2:1 (volume ratio)) and vacuum dried to obtain product B3. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 12h; | 9.1 (1) 3-Isobutylglutaric anhydride (1271 mg, 7.5 mmol) was slowly added to a pyridine solution (5 mL) of 2-dimethylaminoethanol (1 g, 11.2 mmol) and stirred overnight. The excess 2-dimethylaminoethanol and pyridine solution were removed by rotary evaporation to obtain the product organic acid C. Under the catalytic conditions of EDC (191 mg, 1.2 mmol) and DMAP (20 mg, 0.2 mmol), organic acid C (170 mg, 1 mmol) and 2-dodecylhexadecanol (205 mg, 0.5 mmol) were dissolved in 5 mL of CDCl2 and stirred at room temperature for 12 h. The solvent was removed by rotary evaporation to separate the initial product, which was purified by silica gel chromatography (product eluent: n-hexane:ethyl acetate = 2:1 (volume ratio)) and dried in vacuo to obtain product C3. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 12h; | 12.1 (1) 3,3-Dimethylglutaric anhydride (1061 mg, 7.5 mmol) was slowly added to a pyridine solution (5 mL) of 2-dimethylaminoethanol (1 g, 11.2 mmol) and stirred overnight. The excess 2-dimethylaminoethanol and pyridine solution were removed by rotary evaporation to obtain the product organic acid D. Under the catalytic conditions of EDC (191 mg, 1.2 mmol) and DMAP (20 mg, 0.2 mmol), organic acid D (142 mg, 1 mmol) and 2-dodecylhexadecanol (205 mg, 0.5 mmol) were dissolved in 5 mL of CDCl2 and stirred at room temperature for 12 h. The solvent was removed by rotary evaporation to separate the initial product, which was purified by silica gel chromatography (product eluent: n-hexane:ethyl acetate = 2:1 (volume ratio)) and vacuum dried to obtain product D3. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 12h; | 15.1 (1) 3-Methylglutaric anhydride (957 mg, 7.5 mmol) was slowly added to a pyridine solution (5 mL) of 2-dimethylaminoethanol (1 g, 11.2 mmol) and stirred overnight. The excess 2-dimethylaminoethanol and pyridine solution were removed by rotary evaporation to obtain the product organic acid E. Under the catalytic conditions of EDC (191 mg, 1.2 mmol) and DMAP (20 mg, 0.2 mmol), organic acid E (128 mg, 1 mmol) and 2-dodecylhexadecanol (205 mg, 0.5 mmol) were dissolved in 5 mL of CDCl2 and stirred at room temperature for 12 h. The solvent was removed by rotary evaporation to separate the initial product, which was purified by silica gel chromatography (product eluent: n-hexane:ethyl acetate = 2:1 (volume ratio)) and vacuum dried to obtain product E3. |