Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non-UV-Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method
Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non-UV-Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method
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通过新的 log P 测定方法研究（脱氧）氟化对非紫外线活性氟化烷醇和碳水化合物亲脂性的影响
DOI：
10.1002/ange.201509460
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发表时间：
2015
影响因子：
--
通讯作者：
Linclau B
中科院分区：
文献类型：
--
作者：
Linclau B
通过氟化来调整性质对于许多目的来说是非常有效的，目前对脂肪族化合物的研究越来越多。一个重要的应用是脂亲性(LogP)调节。然而，对于非紫外光活性化合物，测定logP是很麻烦的。本文提出了一种新的摇瓶对数值测定方法，可以测量具有或不具有紫外线活性的含氟化合物的对数，而不管它们是亲水的还是亲油的。不需要校准曲线或测量复合质量/等分体积。用该方法测定了氟化作用对含氟脂肪醇亲脂性的影响，并测定了含氟碳水化合物的对数P值。报告了一些有趣的趋势和变化，例如，对相对立体化学的依赖。
Property tuning by fluorination is very effective for a number of purposes, and currently increasingly investigated for aliphatic compounds. An important application is lipophilicity (logP) modulation. However, the determination of logPis cumbersome for non‐UV‐active compounds. A new variation of the shake‐flask logPdetermination method is presented, enabling the measurement of logPfor fluorinated compounds with or without UV activity regardless of whether they are hydrophilic or lipophilic. No calibration curves or measurements of compound masses/aliquot volumes are required. With this method, the influence of fluorination on the lipophilicity of fluorinated aliphatic alcohols was determined, and the logPvalues of fluorinated carbohydrates were measured. Interesting trends and changes, for example, for the dependence on relative stereochemistry, are reported.