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无阻碍酰胺的色谱可分离的构象异构体。

Chromatographically separable rotamers of an unhindered amide.

机构信息

Institut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.

Organisch-Chemisches Institut, Ruprecht-Karls Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

出版信息

Beilstein J Org Chem. 2014 Mar 21;10:701-6. doi: 10.3762/bjoc.10.63. eCollection 2014.

DOI:10.3762/bjoc.10.63
PMID:24778722
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3999880/
Abstract

Surprisingly stable formamide rotamers were encountered in the tetrahydroisoquinoline and morphinan series of alkaloids. We investigated the hindered rotation around the amide bond by dynamic high-performance liquid chromatography (DHPLC) and kinetic measurements of the interconversion of the rotamers which can readily be separated by HPLC as well as TLC. The experimental results of the different methods were compared to each other as well as to results obtained by DFT calculations.

摘要

在四氢异喹啉和吗啡烷生物碱系列中遇到了出人意料的稳定的甲酰胺构象异构体。我们通过动态高效液相色谱法（DHPLC）和对可以通过 HPLC 以及 TLC 轻松分离的构象异构体的互变异构的动力学测量研究了酰胺键周围的受阻旋转。不同方法的实验结果相互进行了比较，并且与通过 DFT 计算获得的结果进行了比较。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/f6ed8314c0bf/Beilstein_J_Org_Chem-10-701-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/405d093f1ace/Beilstein_J_Org_Chem-10-701-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/12e0e56038be/Beilstein_J_Org_Chem-10-701-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/02695d02af91/Beilstein_J_Org_Chem-10-701-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/8bf969d81179/Beilstein_J_Org_Chem-10-701-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/8271e4c9290e/Beilstein_J_Org_Chem-10-701-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/78f4d0d1bf6a/Beilstein_J_Org_Chem-10-701-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/f6ed8314c0bf/Beilstein_J_Org_Chem-10-701-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/405d093f1ace/Beilstein_J_Org_Chem-10-701-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/12e0e56038be/Beilstein_J_Org_Chem-10-701-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/02695d02af91/Beilstein_J_Org_Chem-10-701-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/8bf969d81179/Beilstein_J_Org_Chem-10-701-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/8271e4c9290e/Beilstein_J_Org_Chem-10-701-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/78f4d0d1bf6a/Beilstein_J_Org_Chem-10-701-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/43e8/3999880/f6ed8314c0bf/Beilstein_J_Org_Chem-10-701-g007.jpg

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5
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6
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