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4,6-二甲基-4-壬烯-3-酮的合成
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Abstract:
通过3-戊酮和2-甲基戊醛的羟醛缩合反应，建立了4,6-二甲基-4-壬烯-3-酮的高效合成方法。通过单因素实验考察了反应物配比、催化剂用量、反应时间、溶剂用量和反应温度对产率的影响，结果表明，最佳工艺条件为：n (3-戊酮)：n (2-甲基戊醛)：n (NaOH) = 5:1:0.5，反应时间1.5 h，反应温度75℃，目标产物的产率为92.35%，HPLC质量分数为99.6%。本工艺具有步骤简洁、反应条件温和、反应时间短、收率高、成本低和污染少的优点，适合工业化生产。
An efficient synthesis method of 4,6-dimethyl-4-nonene-3-ketone was established by a hydroxyl aldehyde condensation reaction of 3-pentenone and 2-methylpentaldehyde. Through the single factor experiment, factors influencing the product yield are discussed: such as molratio of raw material, amount of catalyst , reaction time, amount of solvent and reaction temperature. The better conditions for this reaction have been established: n (3-pentanone): n (2-methylpentanal): n (NaOH) = 5:1:0.5, the reaction time is 1.5 h, the reaction temperature is 75？C, and the yield of the target product is 92.35%, and the HPLC mass fraction was 99.6%. The process has the advantages of simple steps, mild reaction conditions, short reaction time, high yield, low cost and less pollution, and it is suitable for industrial production.
| [1] | Das, B., Banerjee, J., Chowdhury, N., Majhi, A. and Holla, H. (2006) Remarkably Chemoselective Reduction of Unmodified Baylis-Hillman Adducts by InCl3/NaBH4: Application to the Stereoselective Synthesis of Trisubstituted Alkenones Including Two Alarm Pheromones. Synlett, No. 12, 1879-1882. |
| [2] | Bestmann, H.J., Attygalle, A.B., Glasbrenner, J., Riemer, R., Vostrowsky, O., Constantino, M.G., Melikian, G. and Morgan, E.D. (1988) Pheromones, 65. Identification of the Volatile Components of the Mandibular Gland Secretion of the Ant Manica Rubida: Structure Elucidation, Synthesis, and Absolute Configuration of Manicone. Liebigs Annalen der Chemie, 1988, 55-60. https://doi.org/10.1002/jlac.198819880111 |
| [3] | 沈伟, 田伟生. 蚂蚁信息素(S)-(+)-Bishomomanicone的合成[C]//中国化学会第26届学术年会有机化学分会场论文集. 天津, 2008: 169. |
| [4] | 孙凌峰, 陈岩. 蚂蚁警戒信息素4-甲基-3-庚酮的合成[C]//中国化学会第四届有机化学学术会议论文集. 昆明, 2005: 218. |
| [5] | Jarvis, A.P., Liebig, J., H？lldobler, B. and Oldham, N.J. (2004) Biosynthesis of the Insect Pheromone (S)-4-methyl- 3-heptanone. Chemical Communications, 21, 1196-1197. https://doi.org/10.1039/B403186E |
| [6] | Koltunov, K.Y., Walspurger, S. and Sommer, J. (2006) Selective, C,C-Double Bond Reduction of α,β-Unsaturated Carbonyl Compounds with Cyclohexane Using Zeolites. Journal of Molecular Catalysis A: Chemical, 245, 231-234.
https://doi.org/10.1016/j.molcata.2005.09.034 |
| [7] | 宋欣沛, 罗丽梅, 郑一敏. 喹啉酮类化合物抗幽门螺杆菌的构效关系研究[J]. 重庆理工大学学报(自然科学), 2019, 33(7): 228-232. |
| [8] | Fischbach, W. and Malfertheiner, P. (2018) Helicobacter Pylori Infection. Deutsches ？rzteblatt Internationa, 115, 429-436.
https://doi.org/10.3238/arztebl.2018.0429 |
| [9] | 杨伶俐, 徐帆, 李全秀. 幽门螺旋杆菌所致消化性溃疡治疗研究进展[J]. 中国医药导报, 2009, 6(7): 7-9. |
| [10] | Wroblewski, L.E. and Peek Jr. R.M. (2013) Helicobacter Pylori in Gastric Carcinogenesis: Mechanisms. Gastroenterology Clinics of North America, 42, 285-298. https://doi.org/10.1016/j.gtc.2013.01.006 |
