A method to search the most stable reaction pathway and its application to the Pinner Pyrimidine Synthesis reaction

Eri Maeyama, Toru Yamaguchi, Michinori Sumimoto, K. Hori
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Abstract

The development of synthetic routes for functional chemicals has been heavily depending on experience and intuition of synthetic organic chemists. In case that target molecules have complex structures, there are many possible synthetic routes, and it is often difficult to determine which one should be adopted. In order to decrease synthesis routes for experiments, we introduced “in silico screening” which requires to search TSs for synthesis routes, we have proposed a method to locate the new TS structure of a target reaction by using TS structures in TSDB. However, this method seldom gives the most stable TS structure within possible conformers. That is, the stability of transition states (TS), reactants and products is highly dependent on initial structures used for optimization. Therefore, this method is likely to give inadequate data to compare calculated and measured values of other synthetic reactions. For these purposes, we have to find reaction mechanisms with the most stable TS and molecules involved in the reactions. In this paper, we proposed a method to search the most stable reaction pathway and applied it to the Pinner Pyrimidine reaction of ethyl 3-oxobutanoate and 3-ethoxypropanimidamide.
寻找最稳定反应途径的方法及其在平纳嘧啶合成反应中的应用
功能化学品合成路线的发展在很大程度上依赖于合成有机化学家的经验和直觉。当目标分子结构复杂时,有许多可能的合成路线,往往难以确定应该采用哪一种。为了减少实验合成路线,我们引入了通过搜索TS来寻找合成路线的“In silico screening”,我们提出了一种利用TSDB中的TS结构来定位目标反应的新TS结构的方法。然而,这种方法很少在可能的构象中给出最稳定的TS结构。也就是说,过渡态(TS)、反应物和产物的稳定性高度依赖于用于优化的初始结构。因此,这种方法可能不能提供足够的数据来比较其他合成反应的计算值和测量值。为了达到这些目的,我们必须找到最稳定的TS和参与反应的分子的反应机制。本文提出了一种寻找最稳定反应途径的方法,并将其应用于3-氧丁酸乙酯与3-乙氧基丙酰胺的平纳嘧啶反应。
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
Journal of Computer Aided Chemistry
Journal of Computer Aided Chemistry CHEMISTRY, MULTIDISCIPLINARY-
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