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

引用次数: 0

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。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

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.