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以α-环柠檬醛(1)为A环合成子,以季膦盐(2)为C环合成子,通过B irch还原反应建立α,β-不饱和酮三元环结构,最后利用异丙基格氏试剂在无水三氯化铈催化下与羰基进行亲核加成反应,同时引入异丙基和羟基,得到目标产物。通过红外光谱检测,在3 418 cm-1处出现典型的羟基吸收峰,表明目标分子中成功地引入了所需官能团。1H NMR核磁共振谱中,在δ0.96、1.83和6.98处分别出现甲基的双重峰、亚甲基的七重峰和羟基氢的吸收等目标产物结构中的特征峰。在13C NMR谱和HRMS谱中,分别得到291.484 6的测定结果和20个C原子在对映位置的吸收峰值。结果表明,与目标产物结构相符,说明成功地合成了目标产物。
The α, β-unsaturated ketone three-membered ring structure was established by the B irch reduction reaction using α-cyclic citral (1) as the ring A synthon and quaternary phosphonium salt (2) as the ring C synthon. Finally, Under the catalysis of anhydrous cerium trichloride, the Grignard reagent undergoes a nucleophilic addition reaction with the carbonyl group, at the same time introducing isopropyl and hydroxyl to obtain the target product. By infrared spectroscopy, a typical hydroxyl absorption peak appeared at 3 418 cm-1, indicating that the desired functional group was successfully introduced into the target molecule. In the 1H NMR spectrum, the characteristic peaks in the structure of the target product such as the doublet of methyl group, the doublet of methylene group and the absorption of hydroxy hydrogen group appear at δ0.96, 1.83 and 6.98, respectively. The results of 291.484 6 and the absorption peaks of 20 C atoms in the enantiomeric positions were obtained respectively in 13C NMR spectrum and HRMS spectrum. The results show that, in accordance with the structure of the target product, indicating the successful synthesis of the target product.