高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (07): 1413-1419.doi: 10.3969/j.issn.0251-0790.2012.07.009

• 分析化学 • 上一篇    下一篇

不对称反应的对映体过量值预测

张庆友1, 张丹丹1, 索净洁1, 李静亚1, 龙海林1, 许禄2   

  1. 1. 河南大学化学化工学院, 环境与分析科学研究所, 开封 475004;
    2. 中国科学院长春应用化学研究所, 长春 130022
  • 收稿日期:2011-11-15 出版日期:2012-07-10 发布日期:2012-07-10
  • 通讯作者: 许 禄, 男, 教授, 博士生导师, 主要从事化学信息学研究. E-mail: luxu@ciac.jl.cn E-mail:luxu@ciac.jl.cn
  • 基金资助:

    国家自然科学基金(批准号: 20875022), 教育部留学回国人员科研启动基金(批准号: 2009-1001)和河南省国际科技合作重点项目基金(批准号: 114300510009)资助.

Prediction of Enantiomeric Excess in Asymmetric Reaction

ZHANG Qing-You1, ZHANG Dan-Dan1, SUO Jing-Jie1, LI Jing-Ya1, LONG Hai-Lin1, XU Lu2   

  1. 1. Institute of Environmental and Analytical Sciences, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China;
    2. Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
  • Received:2011-11-15 Online:2012-07-10 Published:2012-07-10

摘要: 建立了手性催化剂结构与反应产物对映体过量值的定量结构-活性相关性模型, 以辅助苯乙酮不对称氢转移反应的催化剂筛选. 手性催化剂由手性氨醇配体与金属络合物合成, 故采用构象独立手性指数或构象依赖手性指数描述手性氨醇配体, 采用指示变量区分金属络合物, 然后合并2个指数来描述手性催化剂. 通过遗传算法进行变量选择, 采用随机森林法建立数学模型以预测对映体过量值, 测试集的相关系数R2=0.769, 整个数据集的OOB(Out-of-bag)交叉验证结果为R2=0.785.

关键词: 不对称催化, 对映体过量值, 手性催化剂, 构象独立手性指数, 构象依赖手性指数

Abstract: In order to assist enantioselective catalyst screening for asymmetric hydrogen transfer to acetophenone, the model of quantitative structure-activity relationship between the enantiomeric excesses(e.e.) of the products and the structures of the catalysts was constructed. The chiral catalysts can be synthesized by chiral amino alcohol and metal complex precursor, thus, the chiral catalysts were represented by the combination of conformation-independent chirality codes or conformation-dependent chirality codes which were derived from the structures of chiral amino alcohols and indictor variables which were used to distinguish metal complex precursor. The variables selection was performed by genetic algorithm, and then the mathematics model was built by Random Forest to make prediction of e.e. A correlation coefficient of R2=0.769 was obtained for the test set, and the result of out-of-bag(OOB) cross-validation of the whole dataset was R2 =0.785.

Key words: Asymmetric catalysis, Enantiomeric excess, Chiral catalyst, Conformation-independent chirality code, Conformation-dependent chirality code

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