Selective C—H deuterium exchange in the oxacamphanyl moiety linked to the carbamide group

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Russian Chemical Bulletin Pub Date : 2024-08-31 DOI:10.1007/s11172-024-4312-9
A. I. Nichugovskiy, E. A. Eshtukova-Shcheglova, R. R. Fayzullin, D. V. Kuznetsov, V. V. Burmistrov, I. A. Novakov
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Abstract

In the 1H NMR spectra (DMSO-d6) of 1,3-disubstituted ureas containing the 4,7,7-trimethyl-3-oxo-4-oxabicyclo[2.2.1]heptan-1-yl substituent, the signals for the CH2—CH2 moiety appear as an ADMP-type spin system consisting of four doublets of doublets of doublets with chemical shifts in the range from 1.54 to 2.80 ppm. The experiment in CD3OD showed the disappearance of the signal at δ 2.80 and a change in the multiplicity of the other signals, which is indicative of the selective deuterium exchange of one of the four protons of the CH2—CH2 group for a deuterium atom. This allows the selective modification of compounds containing the oxacamphanyl moiety.

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与碳酰胺基团相连的氧杂甘氨酰分子中的选择性 C-H 氘交换
在含有 4,7,7-三甲基-3-氧代-4-氧杂双环[2.2.1]庚烷-1-基取代基的 1,3-二取代脲的 1H NMR 光谱(DMSO-d6)中,CH2-CH2 分子的信号以 ADMP 型自旋系统的形式出现,该系统由四个双音的双音组成,化学位移范围为 1.54 至 2.80 ppm。在 CD3OD 中进行的实验表明,δ 2.80 处的信号消失了,其他信号的多重性发生了变化,这表明 CH2-CH2 基团的四个质子中的一个质子与一个氘原子发生了选择性氘交换。这样就可以对含有氧杂甘氨酰分子的化合物进行选择性修饰。
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来源期刊
Russian Chemical Bulletin
Russian Chemical Bulletin 化学-化学综合
CiteScore
2.70
自引率
47.10%
发文量
257
审稿时长
3-8 weeks
期刊介绍: Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.
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