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具有离域正电荷的新型水溶性异恶唑连接的1,3,4-恶二唑衍生物。

New water-soluble isoxazole-linked 1,3,4-oxadiazole derivative with delocalized positive charge.

作者信息

Bąchor Urszula, Drozd-Szczygieł Ewa, Bąchor Remigiusz, Jerzykiewicz Lucjan, Wieczorek Robert, Mączyński Marcin

机构信息

Department of Organic Chemistry, Faculty of Pharmacy, Wroclaw Medical University Borowska 211A 50-556 Wroclaw Poland

Faculty of Chemistry, University of Wroclaw F. Joliot-Curie 14 50-383 Wrocław Poland

出版信息

RSC Adv. 2021 Sep 3;11(47):29668-29674. doi: 10.1039/d1ra05116d. eCollection 2021 Sep 1.

DOI:10.1039/d1ra05116d
PMID:35479548
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9040910/
Abstract

Herein we present a synthesis and characterization of a new and unique low-weight heterocyclic compound 5-amino-2-(5-amino-3-methyl-1,2-oxazol-4-yl)-3-methyl-2,3-dihydro-1,3,4-oxadiazol-2-ylium bromide with the unusual electron charge delocalization owing the local positive charge at the carbon atom of oxadiazole moiety. X-ray single crystal of CHNO·Br showed the molecule crystalized in monoclinic, space group 2/. Both five membered rings are planar and twisted forming the ring motif with the counter ion where H⋯Br interactions are one of the dominant. The presented compound is characterized by high ionization efficiency in ESI-MS mode and undergoes dissociation within oxadiazole moiety under ESI-MS/MS conditions even under low collision energies. The presented compound is an interesting example of heterocyclic stable carbocation which may serve as a new lead structure.

摘要

在此，我们报道了一种新型独特的低分子量杂环化合物5-氨基-2-(5-氨基-3-甲基-1,2-恶唑-4-基)-3-甲基-2,3-二氢-1,3,4-恶二唑-2-鎓溴化物的合成与表征，由于恶二唑部分碳原子上存在局部正电荷，该化合物具有不寻常的电子电荷离域。CHNO·Br的X射线单晶表明该分子结晶于单斜晶系，空间群为2/。两个五元环都是平面的且扭曲，与抗衡离子形成环结构，其中H⋯Br相互作用是主要作用之一。所报道的化合物在电喷雾电离质谱（ESI-MS）模式下具有高电离效率，并且即使在低碰撞能量下，在ESI-MS/MS条件下也会在恶二唑部分发生解离。所报道的化合物是杂环稳定碳正离子的一个有趣例子，可作为一种新的先导结构。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/0bd591d625c5/d1ra05116d-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/46e1658afabb/d1ra05116d-f2.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/0335ad91bf3e/d1ra05116d-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/f7ab2032eeb2/d1ra05116d-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/559f9a625c1c/d1ra05116d-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/00042f8a8ed3/d1ra05116d-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/0bd591d625c5/d1ra05116d-f9.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/46e1658afabb/d1ra05116d-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/da785f203c38/d1ra05116d-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/abd415597b07/d1ra05116d-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/0335ad91bf3e/d1ra05116d-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/f7ab2032eeb2/d1ra05116d-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/559f9a625c1c/d1ra05116d-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/00042f8a8ed3/d1ra05116d-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/08fd/9040910/0bd591d625c5/d1ra05116d-f9.jpg

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