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| 奈韦拉平闭环前体的量子化学研究与实验 | |
| 引用本文： | 许青青,杨亦文,姜华. 奈韦拉平闭环前体的量子化学研究与实验[J]. 计算机与应用化学, 2012, 29(3): 339-342 |
| 作者姓名： | 许青青 杨亦文 姜华 |
| 作者单位： | 1. 衢州学院化学与材料工程学院,浙江,衢州,324000 2. 浙江大学制药工程研究所,浙江,杭州,310027 |
| 摘 要： | 采用密度泛函B3LYP/6-31G(d)方法对奈韦拉平闭环前体2-环丙胺基-N-(2-氯-4-甲基-3-吡啶基)-3-吡啶甲酰胺进行了量子化学研究,并通过闭环前体在强碱的作用下,在有机溶剂中加热回流合成奈韦拉平进行了实验验证。理论计算结果表明,闭环前体分子稳定性较差,具有较强的反应活性;偶极矩与奈韦拉平差别不是很大;与卤素原子相连的碳原子是亲核取代反应的活性中心,仲胺氮原子和羰基氧原子的亲核性存在着竟争。实验结果显示,强碱的用量是影响闭环反应的主要因素,根据理论计算推测的主要产物和副产物,与实验结果相一致。 |
| 关 键 词： | 密度泛函理论(DFT) 奈韦拉平 闭环前体 合成 |
Quantum chemical and experimental study of closed-loop reactant of nevirapine |
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| Xu Qingqing , Yang Yiwen , Jiang Hua. Quantum chemical and experimental study of closed-loop reactant of nevirapine[J]. Computers and Applied Chemistry, 2012, 29(3): 339-342 | |
| Authors: | Xu Qingqing Yang Yiwen Jiang Hua |
| Affiliation: | 1 (1.College of Chemical and Material engineering,Quzhou University,Quzhou,324000,Zhejiang,China) (2.Institute of Pharmaceutical Engineering,Zhejiang University,Hangzhou,310027,Zhejiang,China) |
| Abstract: | N-(2-Chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide as closed-loop reactant of nevirapine had been theoretically studied by means of DFT-B3LYP/6-31G(d).The present conclusions were experimentally verified by heat refluxing the closed-loop reactant in organic solvent under a strong base condition,to yield nevirapine.Theoretical results indicated that the closed loop reactant molecules display high reaction activity and less stability;Dipole moment difference is not great compared with nevirapine;C atoms connected to halogen atoms is the active center of nucleophilic substitution reaction,there is nucleophilic competition with secondary amine N atom and carbonyl O atoms. Experimental results showed that the quantity of strong base is key factors that affect reactions.The results of calculation were in coincided with the experimental results well. |
| Keywords: | density function theory(DFT) nevirapine closed loop reactant synthesis |
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