3-hydroxy-1-adamantol methanol, English name 3-(Hydroxymethyl) -1-Adamantol, is a white solid at room temperature and pressure, and has poor solubility in water. 3-hydroxy-1-amantadane methanol is a derivative of amantadane and is commonly used as the basic skeleton of functional organic molecules of amantadane. With the high chemical reactivity of primary alcohol units in its structure, it can be used to introduce amantadyl groups into the structure of target organic molecules. In organic synthesis methodology, it is mainly used for structural modification and synthesis of large hindrance organic ligands.
Physical and chemical properties
The 3-hydroxy-1-amantadane methanol structure contains two active hydroxyl units, and its chemical conversion properties mainly focus on these two active hydroxyl units. Due to the influence of steric hindrance, the two hydroxyl groups differ greatly in their reactivity. In organic synthetic chemistry, the difference in the activity of these two hydroxyl groups is often used to selectively modify the two reaction sites of the compound.
Figure 1. Esterification of 3-hydroxy-1-amantadinol
Add 500 ml of dried dichloromethane to 1000 ml reaction bottle, 3-hydroxy-1-amantadinol (21.8 g), HOBT(24.2 g), EDCI (34.4 g), and then slowly add triethylamine and the corresponding carboxylic acid to the reaction mixture under stirring. The resulting reaction mixture was vigorously stirred at room temperature for approximately 24 h. After the reaction, 200 ml of water was added to the reaction mixture to separate the organic phase and wash the organic phase twice with dilute hydrochloric acid. The obtained organic phase was dried with anhydrous sodium sulfate, the desiccant was removed by filtration, and the obtained filtrate was concentrated under vacuum to obtain the esterified target product molecules with a yield of 39 g. [1]
Chemical application
hydroxy-1-amantadyl carbinol is often used to introduce amantadyl groups into the structure of target organic molecules. Its high reactivity and steric effect provide a powerful tool for the synthesis of novel organic molecules. The introduction of adamantane plays an important role in the synthesis of large steric organic ligand, because the introduction of adamantyl groups can improve the stereostructure and solubility of the molecule, thus improving the synthesis efficiency and performance of the organic ligand.
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