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Last of the gem-Difluorocycloalkanes: Synthesis and Characterization of 2,2-Difluorocyclobutyl-Substituted Building Blocks
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-04-16 00:00:00 , DOI: 10.1021/acs.joc.9b00719 Anton V. Chernykh 1 , Kostiantyn P. Melnykov 1, 2 , Nataliya A. Tolmacheva 1 , Ivan S. Kondratov 1, 3 , Dmytro S. Radchenko 1, 2 , Constantin G. Daniliuc 4 , Dmitriy M. Volochnyuk 1, 5 , Sergey V. Ryabukhin 1, 2 , Yuliya O. Kuchkovska 1, 2 , Oleksandr O. Grygorenko 1, 2
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2019-04-16 00:00:00 , DOI: 10.1021/acs.joc.9b00719 Anton V. Chernykh 1 , Kostiantyn P. Melnykov 1, 2 , Nataliya A. Tolmacheva 1 , Ivan S. Kondratov 1, 3 , Dmytro S. Radchenko 1, 2 , Constantin G. Daniliuc 4 , Dmitriy M. Volochnyuk 1, 5 , Sergey V. Ryabukhin 1, 2 , Yuliya O. Kuchkovska 1, 2 , Oleksandr O. Grygorenko 1, 2
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An efficient approach to synthesis of previously unavailable 2-substituted difluorocyclobutane building blocks was developed and applied on a multigram scale. The key step of the synthetic sequence included deoxofluorination of O-protected 2-(hydroxylmethyl)cyclobutanone. Dissociation constants (pKa) and log P values for 2,2-difluorocyclobutaneamine and 2,2-difluorocyclobutanecarboxylic acid or their derivatives were measured and compared with the values obtained for the corresponding 3,3-difluorocyclobutane derivatives and nonfluorinated counterparts. Three-dimensional structures of 2,2- and 3,3-difluorocyclobutanamines were compared using exit vector plot analysis of X-ray crystallographic data.
中文翻译:
宝石的最后部分-二氟环烷烃:2,2-二氟环丁基取代的构建基的合成和表征
开发了一种有效的合成先前无法获得的2-取代的二氟环丁烷结构单元的方法,并已应用于多克规模。合成序列的关键步骤包括O保护的2-(羟甲基)环丁酮的脱氧氟化作用。测量了2,2-二氟环丁烷胺和2,2-二氟环丁烷羧酸或其衍生物的解离常数(p K a)和log P值,并将其与相应的3,3-二氟环丁烷衍生物和非氟化对应物所获得的值进行比较。使用X射线晶体学数据的出口向量图分析比较了2,2-和3,3-二氟环丁胺的三维结构。
更新日期:2019-04-16
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
宝石的最后部分-二氟环烷烃:2,2-二氟环丁基取代的构建基的合成和表征
开发了一种有效的合成先前无法获得的2-取代的二氟环丁烷结构单元的方法,并已应用于多克规模。合成序列的关键步骤包括O保护的2-(羟甲基)环丁酮的脱氧氟化作用。测量了2,2-二氟环丁烷胺和2,2-二氟环丁烷羧酸或其衍生物的解离常数(p K a)和log P值,并将其与相应的3,3-二氟环丁烷衍生物和非氟化对应物所获得的值进行比较。使用X射线晶体学数据的出口向量图分析比较了2,2-和3,3-二氟环丁胺的三维结构。