Efficient Synthesis of the Cyclization Intermediate of Iso E Super

IF 1 4区化学 Q4 CHEMISTRY, PHYSICAL

Kinetics and Catalysis Pub Date : 2026-08-29 DOI:10.1134/S0023158426600185

Qing Zhou, Dongwu Liu, Sumu Wei, Yushan Qiu, Yumeng Ren, Jie Liu, Huidong Zheng

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引用次数: 0

Abstract

The Diels–Alder (DA) reaction between 3-methyl-3-penten-2-one (MP) and myrcene is experimentally examined and theoretically modeled as part of the Iso E Super synthesis process. The results reveal that the DA reaction between MP and myrcene follows a typical electron-demand mechanism, and the para-product (2) is the most stable structure. With the addition of the AlCl₃ catalyst, the reaction energy barrier drops significantly from 132.85 to 61.38 kJ/mol, easing the reaction conditions. The AlCl₃ catalyst exhibits the highest catalytic activity among the catalysts tested, especially in isooctane solvent, of which the conversion of myrcene reaches 88.51% and the total selectivity for the cyclization intermediate of Iso E Super is 92.86%. Additionally, it was observed that increasing the Lewis acidity strength leads to higher conversion and selectivity for the para-product of myrcene. This can be attributed to the enhanced electrophilicity of the second carbon atom in MP upon interaction with the catalyst, which makes it more reactive towards the electron-rich carbon atoms of myrcene.

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Iso E超环化中间体的高效合成

本文对3-甲基-3-戊烯-2-酮（MP）与月桂烯之间的Diels-Alder （DA）反应进行了实验研究，并对其进行了理论模拟，作为Iso E超合成过程的一部分。结果表明，MP与月桂烯之间的DA反应遵循典型的电按需反应机制，副产物(2)结构最稳定。随着AlCl3催化剂的加入，反应能垒从132.85降低到61.38 kJ/mol，反应条件明显改善。AlCl3催化剂表现出最高的催化活性，特别是在异辛烷溶剂中，月桂烯的转化率达到88.51%，Iso E Super的环化中间体的总选择性为92.86%。此外，还观察到，增加刘易斯酸强度可以提高月桂烯副产物的转化率和选择性。这可以归因于MP中第二个碳原子在与催化剂相互作用后的亲电性增强，这使得它对富含电子的月桂烯碳原子的反应性更强。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Kinetics and Catalysis 化学-物理化学

CiteScore

2.10

自引率

27.30%

发文量

审稿时长

6-12 weeks

期刊介绍： Kinetics and Catalysis Russian is a periodical that publishes theoretical and experimental works on homogeneous and heterogeneous kinetics and catalysis. Other topics include the mechanism and kinetics of noncatalytic processes in gaseous, liquid, and solid phases, quantum chemical calculations in kinetics and catalysis, methods of studying catalytic processes and catalysts, the chemistry of catalysts and adsorbent surfaces, the structure and physicochemical properties of catalysts, preparation and poisoning of catalysts, macrokinetics, and computer simulations in catalysis. The journal also publishes review articles on contemporary problems in kinetics and catalysis. The journal welcomes manuscripts from all countries in the English or Russian language.