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-(新戊酰氨基甲基)苯甲醛的重排：一项实验与计算研究

Rearrangement of -(pivaloylaminomethyl)benzaldehydes: an experimental and computational study.

作者信息

Hargitai Csilla, Koványi-Lax Györgyi, Nagy Tamás, Ábrányi-Balogh Péter, Dancsó András, Tóth Gábor, Halász Judit, Pandur Angéla, Simig Gyula, Volk Balázs

机构信息

Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, Hungary.

Medicinal Chemistry Research Group, Research Centre for Natural Sciences, P.O. Box 286, H-1519 Budapest, Hungary.

出版信息

Beilstein J Org Chem. 2020 Jul 13;16:1636-1648. doi: 10.3762/bjoc.16.136. eCollection 2020.

DOI:10.3762/bjoc.16.136
PMID:32733608
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7372232/
Abstract

Treatment of alkoxy-substituted -(pivaloylaminomethyl)benzaldehydes under acidic conditions resulted in the formation of the regioisomeric aldehydes and/or dimer-like products. Detailed NMR studies and single-crystal X-ray measurements supported the structure elucidation of the compounds. DFT calculations were also carried out to clarify the reaction mechanism, and to explain the observed product distributions and structural variances in the dimer-like products. Studies on the transformation of unsubstituted -(pivaloylaminomethyl)benzaldehyde under similar conditions were presented as well.

摘要

在酸性条件下对烷氧基取代的 -（新戊酰氨基甲基）苯甲醛进行处理，会生成区域异构体醛和/或二聚体状产物。详细的核磁共振研究和单晶X射线测量为化合物的结构解析提供了支持。还进行了密度泛函理论计算，以阐明反应机理，并解释二聚体状产物中观察到的产物分布和结构差异。同时也介绍了在类似条件下对未取代的 -（新戊酰氨基甲基）苯甲醛转化的研究。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/074e9be81c01/Beilstein_J_Org_Chem-16-1636-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/2b643311d35e/Beilstein_J_Org_Chem-16-1636-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/0d5310f0c811/Beilstein_J_Org_Chem-16-1636-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/0a203e99856d/Beilstein_J_Org_Chem-16-1636-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/0e0bf7a1c1bf/Beilstein_J_Org_Chem-16-1636-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/57a3b4a58f19/Beilstein_J_Org_Chem-16-1636-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/dfbdae62191a/Beilstein_J_Org_Chem-16-1636-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/4f9d25579d3a/Beilstein_J_Org_Chem-16-1636-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/514d1e7a9dbe/Beilstein_J_Org_Chem-16-1636-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/010cbc763842/Beilstein_J_Org_Chem-16-1636-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/d52a932505ef/Beilstein_J_Org_Chem-16-1636-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/a19b466ecad1/Beilstein_J_Org_Chem-16-1636-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/074e9be81c01/Beilstein_J_Org_Chem-16-1636-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/2b643311d35e/Beilstein_J_Org_Chem-16-1636-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/0d5310f0c811/Beilstein_J_Org_Chem-16-1636-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/0a203e99856d/Beilstein_J_Org_Chem-16-1636-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/0e0bf7a1c1bf/Beilstein_J_Org_Chem-16-1636-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/57a3b4a58f19/Beilstein_J_Org_Chem-16-1636-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/dfbdae62191a/Beilstein_J_Org_Chem-16-1636-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/4f9d25579d3a/Beilstein_J_Org_Chem-16-1636-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/514d1e7a9dbe/Beilstein_J_Org_Chem-16-1636-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/010cbc763842/Beilstein_J_Org_Chem-16-1636-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/d52a932505ef/Beilstein_J_Org_Chem-16-1636-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/a19b466ecad1/Beilstein_J_Org_Chem-16-1636-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2f0/7372232/074e9be81c01/Beilstein_J_Org_Chem-16-1636-g005.jpg

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