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通过酸催化的/-混合5,6-二芳基二吡咯乙烯的氧化大环化反应进行克级卟吩的合成。

Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of /-mixed 5,6-diaryldipyrroethenes.

作者信息

Ono Toshikazu, Xu Ning, Koga Daiki, Ideo Toshihiro, Sugimoto Manabu, Hisaeda Yoshio

机构信息

Department of Chemistry and Biochemistry, Graduate School of Engineering, Center for Molecular Systems (CMS), Kyushu University Fukuoka 819-0395 Japan

PRESTO, Japan Science and Technology Agency (JST) 4-1-8 Honcho Kawaguchi Saitama 332-0012 Japan.

出版信息

RSC Adv. 2018 Nov 26;8(69):39269-39273. doi: 10.1039/c8ra09040h. eCollection 2018 Nov 23.

DOI:10.1039/c8ra09040h
PMID:35558012
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9090978/
Abstract

The gram-scale production of porphycene derivatives is reported. This has been achieved by acid-catalyzed ring closure of an /-mixture of 5,6-diaryldipyrroethenes, resulting in the formation of -tetraarylporphycenes in yields of up to 80%. /-isomerization of the 5,6-diaryldipyrroethenes under acidic conditions was key to proceed the effective macrocyclization.

摘要

报道了卟吩衍生物的克级规模制备。这是通过酸催化5,6-二芳基二吡咯乙烯的/-混合物闭环反应实现的,生成-四芳基卟吩的产率高达80%。5,6-二芳基二吡咯乙烯在酸性条件下的/-异构化是有效进行大环化反应的关键。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc0/9090978/8a8eaa1e4630/c8ra09040h-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc0/9090978/479b37f9983b/c8ra09040h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc0/9090978/b07a84b0fb88/c8ra09040h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc0/9090978/8a8eaa1e4630/c8ra09040h-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc0/9090978/479b37f9983b/c8ra09040h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc0/9090978/b07a84b0fb88/c8ra09040h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dbc0/9090978/8a8eaa1e4630/c8ra09040h-f3.jpg

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2
Manganese(V) Porphycene Complex Responsible for Inert C-H Bond Hydroxylation in a Myoglobin Matrix.锰(V)原卟啉复合物在肌红蛋白基质中导致惰性 C-H 键羟化。
J Am Chem Soc. 2017 Dec 27;139(51):18460-18463. doi: 10.1021/jacs.7b11288. Epub 2017 Dec 14.
3
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Angew Chem Int Ed Engl. 2020 Feb 17;59(8):2998-3027. doi: 10.1002/anie.201904934. Epub 2019 Dec 3.
铁原卟啉肌红蛋白催化的环丙烷化反应:由于卡宾物种的快速形成而加速催化。
J Am Chem Soc. 2017 Dec 6;139(48):17265-17268. doi: 10.1021/jacs.7b10154. Epub 2017 Nov 22.
4
The first synthesis of meso-dicycloalkylporphycenes: ring strain effects on structural and optical properties of isomeric porphyrins.中位-二环烷基卟啉的首次合成:环张力对异构卟啉结构和光学性质的影响。
Chem Commun (Camb). 2017 Nov 14;53(91):12258-12261. doi: 10.1039/c7cc07170a.
5
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Phys Chem Chem Phys. 2017 Sep 27;19(37):25537-25543. doi: 10.1039/c7cp02938a.
6
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Molecules. 2017 May 31;22(6):908. doi: 10.3390/molecules22060908.
7
Porphycenes and Related Isomers: Synthetic Aspects.卟吩及其相关异构体:合成方面。
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8
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9
Spectroscopy and Tautomerization Studies of Porphycenes.卟吩光谱和互变异构研究。
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10
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